Molbank

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 - 03 Aug 2021

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

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

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)

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Open AccessShort Note

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

by

Anatoliy A. Vereshchagin

,

,

,

and

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

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)

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Graphical abstract

Open AccessShort Note

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

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and

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

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)

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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

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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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

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 Special Issue Molecules from Side Reactions II)

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Graphical abstract

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

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)

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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

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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Graphical abstract

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

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,

and

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

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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Graphical abstract

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

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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Graphical abstract

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

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 Special Issue Molecules from Side Reactions II)

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Figure 1

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

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)

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Scheme 1

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

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)

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Graphical abstract

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

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)

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Scheme 1

Open AccessCommunication

Ambient-Temperature Synthesis of (E)-N-(3-(tert-Butyl)-1-methyl-1H-pyrazol-5-yl)-1-(pyridin-2-yl)methanimine

by

Diana Becerra

,

Justo Cobo

and

Juan-Carlos Castillo

Molbank 2021, 2021(3), M1250; https://doi.org/10.3390/M1250 - 07 Jul 2021

Abstract

We report the ambient-temperature synthesis of novel (E)-N-(3-(tert-butyl)-1-methyl-1H-pyrazol-5-yl)-1-(pyridin-2-yl)methanamine 3 in 81% yield by a condensation reaction between 3-(tert-butyl)-1-methyl-1H-pyrazol-5-amine 1 and 2-pyridinecarboxaldehyde 2 in methanol using magnesium sulfate as a drying agent. [...] Read more.

We report the ambient-temperature synthesis of novel (E)-N-(3-(tert-butyl)-1-methyl-1H-pyrazol-5-yl)-1-(pyridin-2-yl)methanamine 3 in 81% yield by a condensation reaction between 3-(tert-butyl)-1-methyl-1H-pyrazol-5-amine 1 and 2-pyridinecarboxaldehyde 2 in methanol using magnesium sulfate as a drying agent. The N-pyrazolyl imine 3 was full characterized by IR, 1D, and 2D NMR spectroscopy, mass spectrometry, and elemental analysis. Full article

(This article belongs to the Special Issue Heterocycle Reactions)

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Figure 1

Open AccessCommunication

Synthesis of the Guanidine Derivative: N-{[(7-(4,5-Dihydro-1H-imidazol-2-yl)-2-(p-tolyl)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene)amino](phenylamino)methylene}benzamide

by

Łukasz Balewski

and

Anita Kornicka

Molbank 2021, 2021(3), M1246; https://doi.org/10.3390/M1246 - 06 Jul 2021

Abstract

The guanidine derivative N-{[(7-(4,5-dihydro-1H-imidazol-2-yl)-2-(p-tolyl)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene)amino](phenylamino)methylene}benzamide (3) has been obtained by the reaction of one measure of N-{[7-(4,5-dihydro-1H-imidazol-2-yl)-2-(p-tolyl)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene]carbamothioyl}benzamide (2) [...] Read more.

The guanidine derivative N-{[(7-(4,5-dihydro-1H-imidazol-2-yl)-2-(p-tolyl)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene)amino](phenylamino)methylene}benzamide (3) has been obtained by the reaction of one measure of N-{[7-(4,5-dihydro-1H-imidazol-2-yl)-2-(p-tolyl)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene]carbamothioyl}benzamide (2) with one measure of aniline in the presence of mercury(II) chloride and triethylamine in anhydrous dimethylformamide. The structure of product 3 was confirmed by ¹H and ¹³C-NMR, infrared spectroscopy, and elemental analysis. Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

Open AccessCommunication

Pyridinium Pentachloridooxomolybdate(V), (PyH)₂[MoOCl₅], Revisited: Single-Crystal X-ray Structure Determination

by

Jaka Šturm

and

Barbara Modec

Molbank 2021, 2021(3), M1249; https://doi.org/10.3390/M1249 - 06 Jul 2021

Abstract

(PyH)₂[MoOCl₅] was obtained in the form of emerald green crystals unintentionally from (PyH)₅[MoOCl₄(H₂O)]₃Cl₂ in acetonitrile. (PyH)₂[MoOCl₅] has been used as a starting material in molybdenum(V) coordination [...] Read more.

(PyH)₂[MoOCl₅] was obtained in the form of emerald green crystals unintentionally from (PyH)₅[MoOCl₄(H₂O)]₃Cl₂ in acetonitrile. (PyH)₂[MoOCl₅] has been used as a starting material in molybdenum(V) coordination chemistry for decades, yet its true identity has not been known until now. The X-ray structure analysis has undoubtedly confirmed the existence of this compound. The [MoOCl₅]²⁻ ion displays the usual structural characteristics of the mononuclear MoO³⁺-containing compounds. Full article

(This article belongs to the Section Structure Determination)

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Figure 1

Open AccessShort Note

(2,3-Dihydro-1H-indol-5-ylmethyl)amine

by

Vladimir A. Ogurtsov

and

Oleg A. Rakitin

Molbank 2021, 2021(3), M1248; https://doi.org/10.3390/M1248 - 05 Jul 2021

Abstract

New (2,3-dihydro-1H-indol-5-ylmethyl)amine was synthesized from 2-((1-acetylindolin-5-yl)methyl)isoindoline-1,3-dione by simultaneous deprotection of phthalimide and acetyl groups. The structure of the newly synthesized compounds was established by elemental analysis, high resolution mass-spectrometry, ¹H, ¹³C NMR and IR spectroscopy and mass-spectrometry. The resulting [...] Read more.

New (2,3-dihydro-1H-indol-5-ylmethyl)amine was synthesized from 2-((1-acetylindolin-5-yl)methyl)isoindoline-1,3-dione by simultaneous deprotection of phthalimide and acetyl groups. The structure of the newly synthesized compounds was established by elemental analysis, high resolution mass-spectrometry, ¹H, ¹³C NMR and IR spectroscopy and mass-spectrometry. The resulting compound is a convenient intermediate for various disubstituted 1-(indolin-5-yl)methanamines, which may be of interest as substances with useful pharmacological properties. Full article

(This article belongs to the Special Issue Heterocycle Reactions)

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Graphical abstract

Open AccessShort Note

tert-Butyl Bis(4′-(Hexyloxy)-[1,1′-biphenyl]-4-yl)carbamate

by

Timofey N. Chmovzh

and

Oleg A. Rakitin

Molbank 2021, 2021(3), M1247; https://doi.org/10.3390/M1247 - 05 Jul 2021

Abstract

New donor building blocks, i.e., triarylamino derivatives, are of great interest for the production of organic photovoltaic materials. In this communication, bis(4′-(hexyloxy)-[1,1′-biphenyl]-4-yl)amine was synthesized in a two-step process via hydrolysis of its tert-butyl carbamate derivative. tert-Butyl bis(4′-(hexyloxy)-[1,1′-biphenyl]-4-yl)carbamate was obtained by Suzuki [...] Read more.

New donor building blocks, i.e., triarylamino derivatives, are of great interest for the production of organic photovoltaic materials. In this communication, bis(4′-(hexyloxy)-[1,1′-biphenyl]-4-yl)amine was synthesized in a two-step process via hydrolysis of its tert-butyl carbamate derivative. tert-Butyl bis(4′-(hexyloxy)-[1,1′-biphenyl]-4-yl)carbamate was obtained by Suzuki cross-coupling reaction of tert-butyl bis(4-bromophenyl)carbamate and (4-(hexyloxy)phenyl)boronic acid in the presence of tetrakis(triphenylphosphine)palladium(0). The structure of newly synthesized compounds was established by means of elemental analysis, high resolution mass-spectrometry, ¹H, ¹³C-NMR, IR and UV spectroscopy and mass-spectrometry. Full article

(This article belongs to the Special Issue Metal-Catalyzed Synthesis)

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Scheme 1

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