Molbank

6 pages, 1634 KiB

Open AccessCommunication

Hybrid Pyridine Bis-Anthracene-Imidazolium Salt: NMR Studies on Zn-Acetate Complexation

by Dorina Amăriucăi-Mantu, Violeta Mangalagiu, Catalina-Ionica Ciobanu and Vasilichia Antoci

Molbank 2021, 2021(3), M1280; https://doi.org/10.3390/M1280 - 14 Sep 2021

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We report here the design and synthesis of a new hybrid bis-anthracene-imidazolium salt, having a pyridine scaffold. NMR studies of dimer generation, as well as complexation with zinc acetate were performed. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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6 pages, 5097 KiB

Open AccessShort Note

2-Oxo-2H-chromen-7-yl 4-chlorobenzoate

by Diana Becerra, Jaime Portilla and Juan-Carlos Castillo

Molbank 2021, 2021(3), M1279; https://doi.org/10.3390/M1279 - 14 Sep 2021

Cited by 6 | Viewed by 3003

Abstract

We describe the synthesis of 2-oxo-2H-chromen-7-yl 4-chlorobenzoate 3 in 88% yield by the O-acylation reaction of 7-hydroxy-2H-chromen-2-one 1 with 4-chlorobenzoyl chloride 2 in dichloromethane using a slight excess of triethylamine at 20 °C for 1 h. The ester [...] Read more.

We describe the synthesis of 2-oxo-2H-chromen-7-yl 4-chlorobenzoate 3 in 88% yield by the O-acylation reaction of 7-hydroxy-2H-chromen-2-one 1 with 4-chlorobenzoyl chloride 2 in dichloromethane using a slight excess of triethylamine at 20 °C for 1 h. The ester 3 was completely characterized by mass spectrometry, IR, UV–Vis, 1D, and 2D NMR spectroscopy. Full article

(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)

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8 pages, 1542 KiB

Open AccessShort Note

4,6-Bis((E)-2-(4′-N,N-diphenylamino-[1,1′-biphenyl]-4-yl)vinyl)-2-phenylpyrimidine

by Lacina Diarra, Françoise Robin-le Guen and Sylvain Achelle

Molbank 2021, 2021(3), M1278; https://doi.org/10.3390/M1278 - 10 Sep 2021

Cited by 1 | Viewed by 1850

Abstract

In this contribution, we designed a 4,6-distyrylpyrimidine chromophore with diphenylamino electron-donating groups and biphenylenevinylene extended π-conjugated linkers. This compound has been synthesized in two steps from 4,6-dimethyl-2-phenylpyrimidine by a double Knoevenagel reaction with 4-bromobenzaldehyde followed by a double Suzuki–Miyaura cross coupling reaction with [...] Read more.

In this contribution, we designed a 4,6-distyrylpyrimidine chromophore with diphenylamino electron-donating groups and biphenylenevinylene extended π-conjugated linkers. This compound has been synthesized in two steps from 4,6-dimethyl-2-phenylpyrimidine by a double Knoevenagel reaction with 4-bromobenzaldehyde followed by a double Suzuki–Miyaura cross coupling reaction with 4-(N,N-diphenylamino)phenylboronic acid. This compound exhibits intense emission in moderately polar solvents as well as in solid state. This compound is characterized by an intense emission solvatochromism with emission ranging from blue in non polar n-heptane to orange in dichloromethane. This chromophore is also sensible to the presence of acid with a bathochromic shift of the charge transfer absorption band and emission quenching. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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7 pages, 1198 KiB

Open AccessShort Note

2,6-Dimethoxybenzyl Bromide

by R. Alan Aitken, Elizabeth A. Saab and Alexandra M. Z. Slawin

Molbank 2021, 2021(3), M1277; https://doi.org/10.3390/M1277 - 7 Sep 2021

Cited by 1 | Viewed by 2044

Abstract

The unstable title compound has been characterized for the first time. Its melting point, UV, IR, ¹H and ¹³C-NMR and high-resolution mass spectra are presented. The X-ray structure has also been determined and shows a rather long C–Br bond perpendicular to [...] Read more.

The unstable title compound has been characterized for the first time. Its melting point, UV, IR, ¹H and ¹³C-NMR and high-resolution mass spectra are presented. The X-ray structure has also been determined and shows a rather long C–Br bond perpendicular to the otherwise planar molecule. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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Graphical abstract

13 pages, 1583 KiB

Open AccessArticle

2-Chloro-4,6-bis{(E)-3-methoxy-4-[(4-methoxybenzyl)oxy]styryl}pyrimidine: Synthesis, Spectroscopic and Computational Evaluation

by Otávio Augusto Chaves, Vitor Sueth-Santiago, Douglas Chaves de Alcântara Pinto, José Carlos Netto-Ferreira, Debora Decote-Ricardo and Marco Edilson Freire de Lima

Molbank 2021, 2021(3), M1276; https://doi.org/10.3390/M1276 - 7 Sep 2021

Cited by 1 | Viewed by 2629

Abstract

A novel curcumin analog namely 2-chloro-4,6-bis{(E)-3-methoxy-4-[(4-methoxybenzyl)oxy]-styryl}pyrimidine (compound 7) was synthesized by three-step reaction. The condensation reaction of protected vanillin with 2-chloro-4,6-dimethylpyrimidine (6) was the most efficient step, resulting in a total yield of 72%. The characterization [...] Read more.

A novel curcumin analog namely 2-chloro-4,6-bis{(E)-3-methoxy-4-[(4-methoxybenzyl)oxy]-styryl}pyrimidine (compound 7) was synthesized by three-step reaction. The condensation reaction of protected vanillin with 2-chloro-4,6-dimethylpyrimidine (6) was the most efficient step, resulting in a total yield of 72%. The characterization of compound 7 was performed by ¹H and ¹³C nuclear magnetic resonance (NMR), as well as high-resolution mass spectrometry. The experimental spectrometric data were compared with the theoretical spectra obtained by the density functional theory (DFT) method, showing a perfect match between them. UV-visible spectroscopy and steady-state fluorescence emission studies were performed for compound 7 in solvents of different polarities and the results were correlated with DFT calculations. Compound 7 showed a solvatochromism effect presenting higher molar extinction coefficient (log ε = 4.57) and fluorescence quantum yield (ϕ = 0.38) in toluene than in acetonitrile or methanol. The simulation of both frontier molecular orbitals (FMOs) and molecular electrostatic potential (MEP) suggested that the experimental spectra profile in toluene was not interfered by a possible charge transfer. These results are an indication of a low probability of compound 7 in reacting with unsaturated phospholipids in future applications as a fluorescent dye in biological systems. Full article

(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)

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Graphical abstract

8 pages, 11675 KiB

Open AccessCommunication

Practical and Asymmetric Synthesis of Apremilast Using Ellman’s Sulfinamide as a Chiral Auxiliary

by Bofei Wang and Fangrui Zhong

Molbank 2021, 2021(3), M1275; https://doi.org/10.3390/M1275 - 2 Sep 2021

Viewed by 4060

Abstract

Herein, we described a new protocol for the asymmetric synthesis of apremilast using tert-butanesulfinamide as a chiral auxiliary. This synthetic route consisted of four steps starting from the commercially available 3-hydroxy-4-methoxybenzaldehyde, and apremilast was accordingly obtained in an overall 56% yield and [...] Read more.

Herein, we described a new protocol for the asymmetric synthesis of apremilast using tert-butanesulfinamide as a chiral auxiliary. This synthetic route consisted of four steps starting from the commercially available 3-hydroxy-4-methoxybenzaldehyde, and apremilast was accordingly obtained in an overall 56% yield and with 95.5% ee. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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6 pages, 1429 KiB

Open AccessCommunication

4-(((4-Methoxyphenyl)amino)methyl)-N,N-dimethylaniline and 2-Methoxy-5-((phenylamino)methyl)phenol

by Peter A. Ajibade and Fartisincha P. Andrew

Molbank 2021, 2021(3), M1274; https://doi.org/10.3390/M1274 - 31 Aug 2021

Viewed by 2627

Abstract

Molecular structures of 4-(((4-methoxyphenyl)amino)methyl)-N,N-dimethylaniline and 2-methoxy-5-((phenylamino)methyl)phenol synthesized via Schiff bases reduction route are reported. The compounds consist of asymmetric units of C₁₆H₂₀N₂O (1) and C₁₄H₁₅NO₂ ( [...] Read more.

Molecular structures of 4-(((4-methoxyphenyl)amino)methyl)-N,N-dimethylaniline and 2-methoxy-5-((phenylamino)methyl)phenol synthesized via Schiff bases reduction route are reported. The compounds consist of asymmetric units of C₁₆H₂₀N₂O (1) and C₁₄H₁₅NO₂ (2) in orthorhombic and monoclinic crystal systems, respectively. Compound 1 consist of intermolecular C11—H11···N2 hydrogen bonding with C11···N21 = 3.463(4) Å. The hydroxyl group in 2 is also involved in intermolecular O2—H2···O2 and O2—H2···O21 hydrogen bonding with O2···O11 = 2.8885(15) Å and O1···O21 = 2.9277(5) Å. The molecular structures of the compounds are stabilized by secondary intermolecular interactions of C1—H1B···O11 and C5—H···(C41, C51, C61, C71) for 1 and H···C, C—H···O and N—H···C for 2. The reported compounds are important starting material for the synthesis of many compounds such as azo dyes and dithiocarbamate. Full article

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4 pages, 349 KiB

Open AccessCommunication

Synthesis of 4-[(1H-Benzimidazol-2-yl)sulfanyl]benzaldehyde and 2-({4-[(1H-Benzimidazol-2-yl)sulfanyl]phenyl}methylidene)hydrazine-1-carbothioamide

by Mustafa Turki Ubeid, Hamdy Khamees Thabet and Mohamed Yousef Abu Shuheil

Molbank 2021, 2021(3), M1273; https://doi.org/10.3390/M1273 - 26 Aug 2021

Cited by 4 | Viewed by 3373

Abstract

Here we describe the preparation of 2-(4-((1H-benzo[d]imidazol-2-yl)thio)-benzylidene)-hydrazine-1-carbothioamide in two steps. In the first step, 1,3-dihydro-2H-1,3-benzimidazole-2-thione was reacted with 4-fluorobenzaldehyde in DMSO to get 4-[(1H-benzimidazol-2-yl)sulfanyl]benzaldehyde in high yield. The reaction of the obtained aldehyde with thiosemicarbazide in ethanol at reflux [...] Read more.

Here we describe the preparation of 2-(4-((1H-benzo[d]imidazol-2-yl)thio)-benzylidene)-hydrazine-1-carbothioamide in two steps. In the first step, 1,3-dihydro-2H-1,3-benzimidazole-2-thione was reacted with 4-fluorobenzaldehyde in DMSO to get 4-[(1H-benzimidazol-2-yl)sulfanyl]benzaldehyde in high yield. The reaction of the obtained aldehyde with thiosemicarbazide in ethanol at reflux temperature yielded 2-({4-[(1H-benzimidazol-2-yl)sulfanyl]phenyl}methylidene)hydrazine-1-carbothioamide. The structure of the synthesized compounds was established by NMR spectroscopy (¹H, ¹³C), mass spectrometry, and infrared spectroscopy. Full article

(This article belongs to the Special Issue Nitrogen-Containing Molecules: Natural and Synthetic Products Including Coordination Compounds)

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Scheme 1

5 pages, 8029 KiB

Open AccessShort Note

3-(3-Hydroxypropyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxaldehyde Methyl Hemiacetal

by Massimiliano Cordaro

Molbank 2021, 2021(3), M1272; https://doi.org/10.3390/M1272 - 20 Aug 2021

Viewed by 1703

Abstract

The synthesis of 3-(3-hydroxypropyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxaldehyde as a stable methyl hemiacetal through a convenient 3-step procedure is reported. The molecule is multifunctional as it contains a formyl group, a hydroxyl group and the imide moiety. Each of these groups can play a role in specific [...] Read more.

The synthesis of 3-(3-hydroxypropyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxaldehyde as a stable methyl hemiacetal through a convenient 3-step procedure is reported. The molecule is multifunctional as it contains a formyl group, a hydroxyl group and the imide moiety. Each of these groups can play a role in specific transformations or uses. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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Graphical abstract

5 pages, 572 KiB

Open AccessShort Note

5-(2,6-Diacetamidopyridin-4-yl)-kryptoBODIPY

by Massimiliano Cordaro and Mariachiara Trapani

Molbank 2021, 2021(3), M1271; https://doi.org/10.3390/M1271 - 13 Aug 2021

Viewed by 1808

Abstract

The development of new dyes for various fields of application is of primary interest for the scientific community, among these BODIPY are widely studied for their versatility. This communication describes the synthesis of a BODIPY dye on which a diacetoamidopyridine moiety is connected [...] Read more.

The development of new dyes for various fields of application is of primary interest for the scientific community, among these BODIPY are widely studied for their versatility. This communication describes the synthesis of a BODIPY dye on which a diacetoamidopyridine moiety is connected in meso position. The synthesis procedure requires a one-pot step and the dye is obtained with a yield of 20%. The diacetoamido portion contains chemical functionalities able to favor the interaction of BODIPY with complementary molecules, such as uracil or thymine, offering potential applications for the design of new functional materials or sensors. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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Graphical abstract

12 pages, 1430 KiB

Open AccessShort Note

2-((E)-2-((E)-4-Chloro-5-(2-((E)-5-methoxy-3,3-dimethyl-1-(3-phenylpropyl)indolin-2-ylidene) ethylidene)-1,1-dimethyl-1,2,5,6-tetrahydropyridin-1-ium-3-yl)vinyl)-5-methoxy-3,3-dimethyl-1-(3-phenylpropyl)-3H-indol-1-ium

by Emmanuel Ramsey Buabeng and Maged Henary

Molbank 2021, 2021(3), M1270; https://doi.org/10.3390/M1270 - 11 Aug 2021

Cited by 3 | Viewed by 2325

Abstract

A heptamethine fluorophore, ERB-60, has been synthesized efficiently in four steps in a good yield. The structure of this fluorophore consists of an electron-donating group (methoxy), a hydrophobic moiety (phenylpropyl) with a rotatable bond, a quaternary ammonium fragment, and indolium rings at [...] Read more.

A heptamethine fluorophore, ERB-60, has been synthesized efficiently in four steps in a good yield. The structure of this fluorophore consists of an electron-donating group (methoxy), a hydrophobic moiety (phenylpropyl) with a rotatable bond, a quaternary ammonium fragment, and indolium rings at the terminal ends connected via polymethine chain. All these inherent chemical features fine-tuned the optical properties of the fluorophore. This compound was characterized by both ¹H NMR, ¹³C NMR and mass spectra. The optical properties, including molar absorptivity, fluorescence, Stokes’s shift, and quantum yield, were measured in different solvents such as DMSO, DMF, MeCN, i-PrOH, MeOH, and H₂O. The wavelengths of maximum absorbance of ERB-60 were found to be in the range of 745–770 nm based on the solvents used. In decreasing order, the maximum wavelength of absorbance of ERB-60 in the tested solvents was DMSO > DMF > i-PrOH > MeOH > MeCN > H₂O while the decreasing order of the extinction coefficient was found to be MeCN > MeOH > DMSO > i-PrOH > H₂O > DMF. ERB-60 was found to be more photostable than IR-786 iodide, a commercially available dye, and brighter than the FDA-approved dye, indocyanine green (ICG). Full article

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4 pages, 486 KiB

Open AccessShort Note

(E)-3-[4-(1H-Imidazol-1-yl)phenyl]-1-(4-methylphenyl)prop-2-en-1-one

by Nicholas Bailey and Bradley O. Ashburn

Molbank 2021, 2021(3), M1269; https://doi.org/10.3390/M1269 - 10 Aug 2021

Cited by 1 | Viewed by 2037

Abstract

Imidazole-containing chalcones have been shown to be strongly effective against Aspergillusfumigatus, the causative agent for the disease pulmonary aspergillosis. Claisen–Schmidt condensation of 4-(1H-imidazol-1-yl)benzaldehyde with 4′-methylacetophenone using aqueous sodium hydroxide in methanol yielded the novel compound (E)-3-[4-(1H [...] Read more.

Imidazole-containing chalcones have been shown to be strongly effective against Aspergillusfumigatus, the causative agent for the disease pulmonary aspergillosis. Claisen–Schmidt condensation of 4-(1H-imidazol-1-yl)benzaldehyde with 4′-methylacetophenone using aqueous sodium hydroxide in methanol yielded the novel compound (E)-3-[4-(1H-imidazol-1-yl)phenyl]-1-(4-methylphenyl)prop-2-en-1-one in good yield and purity after recrystallization from hot methanol. With the known antifungal properties of these combined pharmacophores, this novel compound is suitable for anti-aspergillus activity study. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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Graphical abstract

6 pages, 1463 KiB

Open AccessShort Note

(±)-2-{[4-(4-Bromophenyl)-5-phenyl-4H-1,2,4-triazol-3-yl]sulfanyl}-1-phenyl-1-ethanol

by Milenca Mariana Vorga and Valentin Badea

Molbank 2021, 2021(3), M1268; https://doi.org/10.3390/M1268 - 6 Aug 2021

Viewed by 2506

Abstract

The novel racemic secondary alcohol (±)-2-{[4-(4-bromophenyl)-5-phenyl-4H-1,2,4-triazol-3-yl]sulfanyl}-1-phenyl-1-ethanol (12) has been successfully synthesized through S-alkylation of 4-(4-bromophenyl)-5-phenyl-4H-1,2,4-triazole-3-thiol (10) in alkaline medium with 2-bromo-1-phenylethanone followed by reduction of the corresponding ketone 11. All the synthesized compounds [...] Read more.

The novel racemic secondary alcohol (±)-2-{[4-(4-bromophenyl)-5-phenyl-4H-1,2,4-triazol-3-yl]sulfanyl}-1-phenyl-1-ethanol (12) has been successfully synthesized through S-alkylation of 4-(4-bromophenyl)-5-phenyl-4H-1,2,4-triazole-3-thiol (10) in alkaline medium with 2-bromo-1-phenylethanone followed by reduction of the corresponding ketone 11. All the synthesized compounds were characterized by IR, 1D (¹H, ¹³C, DEPT135) and 2D (¹H-¹H, ¹H-¹³C and ¹H-¹⁵N) NMR spectroscopy, elemental analysis and HRMS spectrometry. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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Scheme 1

7 pages, 8643 KiB

Open AccessShort Note

2-Diphenylphosphinomethyl-3-methylpyrazine

by Tiziana Boccuzzi, Luciana Cicco, Andrea Francesca Quivelli, Paola Vitale, Filippo Maria Perna, Konstantin Karaghiosoff and Vito Capriati

Molbank 2021, 2021(3), M1267; https://doi.org/10.3390/M1267 - 5 Aug 2021

Viewed by 2136

Abstract

The lateral metalation-electrophilic trapping reaction of alkyl-substituted pyrazines has always been challenging and poorly regioselective, with the corresponding derivatives often being isolated in moderate yield. In this contribution, we first report on the preparation of an unsymmetrically-substituted pyrazine, that is 2-diphenylphosphinomethyl-3-methylpyrazine, by subjecting [...] Read more.

The lateral metalation-electrophilic trapping reaction of alkyl-substituted pyrazines has always been challenging and poorly regioselective, with the corresponding derivatives often being isolated in moderate yield. In this contribution, we first report on the preparation of an unsymmetrically-substituted pyrazine, that is 2-diphenylphosphinomethyl-3-methylpyrazine, by subjecting to metalation with n-BuLi the commercially available 2,3-dimethylpyrazine, followed by interception of the putative lithiated benzyl-type intermediate with Ph₂PCl. Such a functionalization has been successfully carried out in the absence of additional ligands, working either in THF at −78 °C or in a more environmentally friendly solvent like cyclopentyl methyl ether at 0 °C, with the desired phosphine derivative being isolated in 70–85% yield. The newly synthesized adduct has been fully characterized by means of multinuclear magnetic resonance spectroscopic techniques, and also by preparing a selenium derivative, which furnished single crystals that were suitable for X-ray analysis. Full article

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4 pages, 402 KiB

Open AccessCommunication

4-Aminoalkyl Quinolin-2-one Derivatives via Knorr Cyclisation of ω-Amino-β-Keto Anilides

by Plamen Angelov, Stilyana Velichkova and Pavel Yanev

Molbank 2021, 2021(3), M1266; https://doi.org/10.3390/M1266 - 5 Aug 2021

Cited by 2 | Viewed by 2139

Abstract

In a high-yielding and solvent-free procedure N-ethoxycarbonyl protected ω-amino-β-keto anilides undergo Knorr cyclisation in neat polyphosphoric acid to provide straightforward route to 4-aminoalkyl quinolin-2-one derivatives with variable length of the alkyl chain. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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Scheme 1

3 pages, 1247 KiB

Open AccessShort Note

4-Chlorobenzyl Chloride

by R. Alan Aitken and Alexandra M. Z. Slawin

Molbank 2021, 2021(3), M1265; https://doi.org/10.3390/M1265 - 4 Aug 2021

Viewed by 2279

Abstract

The X-ray structure of the title compound has been determined for the first time. Its molecular structure is in good agreement with those previously determined for similar benzyl halides and the angles between the ring–Cl bonds in adjacent molecules show values in good [...] Read more.

The X-ray structure of the title compound has been determined for the first time. Its molecular structure is in good agreement with those previously determined for similar benzyl halides and the angles between the ring–Cl bonds in adjacent molecules show values in good agreement with an early Zeeman quadrupole spectroscopy study. Full article

(This article belongs to the Section Structure Determination)

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4 pages, 543 KiB

Open AccessShort Note

2-Hydroxy-3-octyloxybenzaldehyde

by Julia V. Novoselova, Anatoliy A. Vereshchagin, Arseniy Y. Kalnin, Daniil A. Lukyanov and Oleg V. Levin

Molbank 2021, 2021(3), M1264; https://doi.org/10.3390/M1264 - 3 Aug 2021

Viewed by 2272

Abstract

Herein, we report the chromatography-free synthesis of 2-hydroxy-3-octyloxybenzaldehyde by the alkylation of 2,3-dihydroxybenzaldehyde as a promising precursor for new SalEn-type complexes with transition metals. The structure of the product is elucidated by means of ¹H and ¹³C-NMR spectra, high-resolution mass spectrometry [...] Read more.

Herein, we report the chromatography-free synthesis of 2-hydroxy-3-octyloxybenzaldehyde by the alkylation of 2,3-dihydroxybenzaldehyde as a promising precursor for new SalEn-type complexes with transition metals. The structure of the product is elucidated by means of ¹H and ¹³C-NMR spectra, high-resolution mass spectrometry with electrospray ionization (ESI-HRMS) and Fourier-transform infrared spectroscopy (FTIR). Full article

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Graphical abstract

3 pages, 329 KiB

Open AccessShort Note

4′,4′′′,4′′′′′-Nitrilotris(4-methoxy-[1,1′-biphenyl]-3-carbaldehyde)

by Anatoliy A. Vereshchagin, Julia V. Novoselova, Arseniy Y. Kalnin, Daniil A. Lukyanov and Oleg V. Levin

Molbank 2021, 2021(3), M1263; https://doi.org/10.3390/M1263 - 31 Jul 2021

Viewed by 2488

Abstract

Multipodal salicylaldehydes have attracted much scientific interest as scaffolds for the construction of multinuclear complexes, as well as metal and covalent organic frameworks. Herein, we report a preparation of 4′,4′′′,4′′′′′-nitrilotris(4-methoxy-[1,1′-biphenyl]-3-carbaldehyde), a direct precursor for the tripodal salicylaldehyde with triphenylamine core. The structure of [...] Read more.

Multipodal salicylaldehydes have attracted much scientific interest as scaffolds for the construction of multinuclear complexes, as well as metal and covalent organic frameworks. Herein, we report a preparation of 4′,4′′′,4′′′′′-nitrilotris(4-methoxy-[1,1′-biphenyl]-3-carbaldehyde), a direct precursor for the tripodal salicylaldehyde with triphenylamine core. The structure of the product was confirmed by molecular spectroscopy. The reported approach may be broadened over a variety of multipodal salicylaldehydes. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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Graphical abstract

5 pages, 689 KiB

Open AccessShort Note

1-Tosyl-6-vinyl-4,5,6,7-tetrahydro-1H-benzo [d] imidazole-2-amine

by Fiach B. Meany, Sarah O’Rourke and Paul V. Murphy

Molbank 2021, 2021(3), M1262; https://doi.org/10.3390/M1262 - 31 Jul 2021

Viewed by 2395

Abstract

The alkene functionalised 2-aminobenzimidazole ring found in terrazoanthine natural products was synthesized in 3 steps from 1,2-epoxy-4-vinylcyclohexane via epoxide ring opening with toluenesulphonamide yielding 2 regioisomeric, separable amino alcohols. One isomer was oxidized to the corresponding ketone and subsequently condensed with cyanamide to [...] Read more.

The alkene functionalised 2-aminobenzimidazole ring found in terrazoanthine natural products was synthesized in 3 steps from 1,2-epoxy-4-vinylcyclohexane via epoxide ring opening with toluenesulphonamide yielding 2 regioisomeric, separable amino alcohols. One isomer was oxidized to the corresponding ketone and subsequently condensed with cyanamide to furnish the title compound, which was characterized by ¹H-NMR and ¹³C-NMR spectroscopy. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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Figure 1

4 pages, 525 KiB

Open AccessShort Note

4,4′-Di-tert-butyl-2,2′-bipyridinium Trifluoromethanesulfonate

by Shintaro Kodama, Kazuki Bunno, Akihiro Nomoto and Akiya Ogawa

Molbank 2021, 2021(3), M1261; https://doi.org/10.3390/M1261 - 28 Jul 2021

Cited by 1 | Viewed by 2880

Abstract

4,4′-Di-tert-butyl-2,2′-bipyridinium trifluoromethanesulfonate was synthesized by stirring 4,4′-Di-tert-butyl-2,2′-bipyridine with scandium(III) trifluoromethanesulfonate in acetonitrile, followed by precipitation with diethyl ether. The structure of the new compound was characterized by FT-IR, ¹H, ¹³C{¹H} and ¹⁹F{¹H} [...] Read more.

4,4′-Di-tert-butyl-2,2′-bipyridinium trifluoromethanesulfonate was synthesized by stirring 4,4′-Di-tert-butyl-2,2′-bipyridine with scandium(III) trifluoromethanesulfonate in acetonitrile, followed by precipitation with diethyl ether. The structure of the new compound was characterized by FT-IR, ¹H, ¹³C{¹H} and ¹⁹F{¹H} NMR spectroscopy and CHN elemental analysis. This is a safe and simple method to obtain mono-protonated bipyridinium trifluoromethanesulfonate without the direct use of trifluoromethanesulfonic acid. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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4 pages, 969 KiB

Open AccessShort Note

N-(Benzo[d]thiazol-2-yl)-2-(2-fluoro-[1,1′-biphenyl]-4-yl)propanamide

by Stanimir Manolov, Iliyan Ivanov and Dimitar Bojilov

Molbank 2021, 2021(3), M1260; https://doi.org/10.3390/M1260 - 26 Jul 2021

Viewed by 2019

Abstract

N-(Benzo[d]thiazol-2-yl)-2-(2-fluoro-[1,1′-biphenyl]-4-yl)propanamide was prepared by a reaction between benzo[d]thiazol-2-amine and flurbiprofen in high yield. The newly obtained flurbiprofen derivative was fully analyzed and characterized via ¹H, ¹³C, UV, IR, and mass spectral data. Full article

(This article belongs to the Section Structure Determination)

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7 pages, 1899 KiB

Open AccessShort Note

Poly[3-methyl-1,3-oxazolidin-2-iminium[µ₃-cyanido-tri-µ₂-cyanido-κ⁹C:N-tricuprate(I)]]

by Leena N. Rachid and Peter W. R. Corfield

Molbank 2021, 2021(3), M1259; https://doi.org/10.3390/M1259 - 26 Jul 2021

Viewed by 1984

Abstract

The unexpected formation of an oxazole ring has occurred during synthesis of a copper(I) cyanide network polymer as part of our ongoing studies of the structural chemistry of these networks. Crystals of the title compound were formed during the synthesis of a previously [...] Read more.

The unexpected formation of an oxazole ring has occurred during synthesis of a copper(I) cyanide network polymer as part of our ongoing studies of the structural chemistry of these networks. Crystals of the title compound were formed during the synthesis of a previously reported CuCN network solid containing protonated N-methylethanolamine and have been characterized by single crystal X-ray structure analysis. The structure shows well-defined oxazole-2-iminium cations sitting in continuous channels along the short a-axis of the crystal in a new three-dimensional copper(I) cyanide polymeric network. Evidently, a reaction has occurred between the cyanide ion and the protonated N-methylethanolamine base. Full article

(This article belongs to the Collection Molecules from Side Reactions)

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12 pages, 1628 KiB

Open AccessCommunication

2-Hydroxy-5-(3,5,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenyl (E)-3-(4-hydroxy-3-methoxyphenyl)acrylate: Synthesis, In Silico Analysis and In Vitro Pharmacological Evaluation

by Antonella Brizzi, Alfonso Trezza, Ottavia Spiga, Samuele Maramai, Francesco Scorzelli, Simona Saponara and Fabio Fusi

Molbank 2021, 2021(3), M1258; https://doi.org/10.3390/M1258 - 23 Jul 2021

Cited by 1 | Viewed by 2406

Abstract

Quercetin and ferulic acid are two phytochemicals extensively represented in the plant kingdom and daily consumed in considerable amounts through diets. Due to a common phenolic structure, these two molecules share several pharmacological properties, e.g., antioxidant and free radical scavenging, anti-cancer, anti-inflammatory, anti-arrhythmic, [...] Read more.

Quercetin and ferulic acid are two phytochemicals extensively represented in the plant kingdom and daily consumed in considerable amounts through diets. Due to a common phenolic structure, these two molecules share several pharmacological properties, e.g., antioxidant and free radical scavenging, anti-cancer, anti-inflammatory, anti-arrhythmic, and vasorelaxant. The aim of the present work was the combination of the two molecules in a single chemical entity, conceivably endowed with more efficacious vasorelaxant activity. Preliminary in silico studies herein described suggested that the new hybrid compound bound spontaneously and with high affinity on the K_Ca1.1 channel. Thus, the synthesis of the 3′-ferulic ester derivative of quercetin was achieved and its structure confirmed by ¹H- and ¹³C-NMR spectra, HSQC and HMBC experiments, mass spectrometry, and elementary analysis. The effect of the new hybrid compound on vascular K_Ca1.1 and Ca_V1.2 channels revealed a partial loss of the stimulatory activity that characterizes the parent compound quercetin. Therefore, further studies are necessary to identify a better strategy to improve the vascular properties of this flavonoid. Full article

(This article belongs to the Special Issue Innovative Approaches to Modify Polyphenols)

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4 pages, 675 KiB

Open AccessShort Note

N-(2,2-Diphenylethyl)-2-(6-methoxynaphthalen-2-yl)propanamide

by Stanimir Manolov, Iliyan Ivanov and Dimitar Bojilov

Molbank 2021, 2021(3), M1257; https://doi.org/10.3390/M1257 - 23 Jul 2021

Viewed by 2324

Abstract

N-(2,2-Diphenylethyl)-2-(6-methoxynaphthalen-2-yl)propanamide was prepared by a reaction between 2,2-diphenylethan-1-amine and naproxen in high yield. The newly obtained naproxen derivative was fully analyzed and characterized via ¹H, ¹³C, UV, IR, and mass spectral data. Full article

(This article belongs to the Section Structure Determination)

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6 pages, 1187 KiB

Open AccessShort Note

9a-Phenyl-2,3,3a,3b,9a,9b-hexahydro-4H-furo[3‘,2’:3,4]cyclobuta- [1,2-b]chromen-4-one: A Flavone-Based [2 + 2]-Photocycloadduct

by Jens Lefarth, Jörg Neudörfl and Axel G. Griesbeck

Molbank 2021, 2021(3), M1256; https://doi.org/10.3390/M1256 - 23 Jul 2021

Cited by 4 | Viewed by 2333

Abstract

The intermolecular [2 + 2]-photocycloaddition of the parent flavone molecule (4) as the triplet energy-accepting species and the electron-rich alkene 2, 3-dihydrofuran (5) was performed by visible-light-mediated triplet-sensitization with an iridium-based organometallic sensitizer. The reaction proceeds with high diastereo- [...] Read more.

The intermolecular [2 + 2]-photocycloaddition of the parent flavone molecule (4) as the triplet energy-accepting species and the electron-rich alkene 2, 3-dihydrofuran (5) was performed by visible-light-mediated triplet-sensitization with an iridium-based organometallic sensitizer. The reaction proceeds with high diastereo- and regioselectivity (>98:2 for the regiochemical orientation and with 95% d.s.). In contrast to numerous other ene/enone combinations that are described in the literature and were also performed by us, the reaction between 4 and 5 almost solely afforded the cis-syn-cis cyclobutane 6, whereas analogous conjugated six- and five-membered cycloalkenones preferentially react to cis-anti-cis cyclobutanes or a mixture of both diastereoisomers (e.g., for the cyclohexanone-derived example 9). Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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5 pages, 1259 KiB

Open AccessShort Note

N,N-Bis(hexyl α-d-acetylmannosyl) Acrylamide

by Atsushi Miyagawa, Shinya Ohno and Hatsuo Yamamura

Molbank 2021, 2021(3), M1255; https://doi.org/10.3390/M1255 - 22 Jul 2021

Cited by 1 | Viewed by 2300

Abstract

Glycosyl monomers for the assembly of multivalent ligands are typically synthesized using carbohydrates with biological functions and polymerizable functional groups such as acrylamide or styrene introduced into the carbohydrate aglycon, and monomers polymerized using a radical initiator. Herein, we report the acryloylation of [...] Read more.

Glycosyl monomers for the assembly of multivalent ligands are typically synthesized using carbohydrates with biological functions and polymerizable functional groups such as acrylamide or styrene introduced into the carbohydrate aglycon, and monomers polymerized using a radical initiator. Herein, we report the acryloylation of 6-aminohexyl α-d-mannoside and its conversion into the glycosyl monomer bearing an acrylamide group. The general acryloylation procedure afforded the desired N-hexyl α-d-acetylmannosyl acrylamide monomer as well as an unexpected compound with a close R_f value. The compounds were separated and analyzed by nuclear magnetic resonance spectroscopy and mass spectrometry, which revealed the unknown compound to be the bivalent N,N-bis(hexyl α-d-acetylmannosyl) acrylamide monomer, which contains two hexyl mannose units and one acrylamide group. To the best of our knowledge, this side reaction has not previously been disclosed, and may be useful for the construction of multivalent sugar ligands. Full article

(This article belongs to the Collection Molecules from Side Reactions)

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4 pages, 822 KiB

Open AccessShort Note

Thiophene-3-carbonyl Chloride

by R. Alan Aitken and Alexandra M. Z. Slawin

Molbank 2021, 2021(3), M1254; https://doi.org/10.3390/M1254 - 22 Jul 2021

Viewed by 2005

Abstract

The X-ray structure of the title compound has been determined for the first time. It shows the ring flip disorder common among thiophene-3-carbonyl derivatives and the occurrence of this phenomenon in the structures of such compounds is discussed. Full article

(This article belongs to the Section Structure Determination)

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3 pages, 477 KiB

Open AccessShort Note

4-Chloro-6-(chloromethyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine

by Vladimir A. Ogurtsov and Oleg A. Rakitin

Molbank 2021, 2021(3), M1253; https://doi.org/10.3390/M1253 - 22 Jul 2021

Cited by 2 | Viewed by 2285

Abstract

A novel 4-chloro-6-(chloromethyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine was prepared by a rational and short two-step synthesis from commercially available ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate via 6-(chloromethyl)-1-methyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one. The structure of the synthesized compounds was established by elemental analysis, high-resolution mass-spectrometry, ¹ [...] Read more.

A novel 4-chloro-6-(chloromethyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine was prepared by a rational and short two-step synthesis from commercially available ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate via 6-(chloromethyl)-1-methyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one. The structure of the synthesized compounds was established by elemental analysis, high-resolution mass-spectrometry, ¹H, ¹³C-NMR and IR spectroscopy and mass-spectrometry. 4-Chloro-6-(chloromethyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine is a convenient intermediate for various disubstituted 1-methyl-1H-pyrazolo[3,4-d]pyrimidines, which may be of interest as substances with useful pharmacological properties. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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6 pages, 1436 KiB

Open AccessShort Note

1-(4-Formyl-2,6-dimethoxyphenoxy)-4-chlorobut-2-yne

by Jérôme Husson

Molbank 2021, 2021(3), M1252; https://doi.org/10.3390/M1252 - 21 Jul 2021

Viewed by 1848

Abstract

A reaction of biomass-derived aldehyde synringaldehyde and half an equivalent of 1,4-dichlorobut-2-yne was attempted in order to obtain a bis-aldehyde with an alkyne spacer. The reaction was carried out in a basic media to effect bis O-alkylation, as described in literature for [...] Read more.

A reaction of biomass-derived aldehyde synringaldehyde and half an equivalent of 1,4-dichlorobut-2-yne was attempted in order to obtain a bis-aldehyde with an alkyne spacer. The reaction was carried out in a basic media to effect bis O-alkylation, as described in literature for the preparation of structurally similar compounds. Nevertheless, only mono alkylation was observed. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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10 pages, 1335 KiB

Open AccessCommunication

Synthesis of Aminopropyltriethoxysilyl-Substituted Imines and Amides

by Surya R. Banks, J. Tanner Morningstar and Mark E. Welker

Molbank 2021, 2021(3), M1251; https://doi.org/10.3390/M1251 - 18 Jul 2021

Cited by 3 | Viewed by 2877

Abstract

A series of small molecules containing aminopropyltriethoxysilyl-substituted imines and amides were synthesized so that they could potentially be incorporated into self-assembled monolayers (SAMs) on metal oxide surfaces. Simple one-step imine preparations and two-step amide preparations are reported here. Full article

(This article belongs to the Section Organic Synthesis and Biosynthesis)

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