Molbank

8 pages, 1299 KiB

Open AccessCommunication

¹H NMR Chemical Shift Changes as a Result of Introduction of Carbonyl-Containing Protecting Groups Observed in Bornol and Isoborneol

by Baohe Lyu, Honoka Sako, Mio Sugiura, Yoshikazu Hiraga, Ryukichi Takagi and Satomi Niwayama

Molbank 2024, 2024(4), M1899; https://doi.org/10.3390/M1899 - 11 Oct 2024

Abstract

Complete assignments of the ¹H NMR chemical shifts for monoterpenes, borneol, and isoborneol, and their derivatives in which the secondary hydroxy group is protected with an acetyl group or a benzoyl group, have been made in CDCl₃ and C₆D [...] Read more.

Complete assignments of the ¹H NMR chemical shifts for monoterpenes, borneol, and isoborneol, and their derivatives in which the secondary hydroxy group is protected with an acetyl group or a benzoyl group, have been made in CDCl₃ and C₆D₆. Upon the protection of the hydroxy group with the carbonyl functional groups, or acetyl or benzoyl groups, many protons constituting the bicyclic ring exhibited downfield and upfield shifts in the chemical shift values, aiding in the unambiguous assignments of protons and carbons. Full article

(This article belongs to the Section Structure Determination)

► Show Figures

Figure 1

5 pages, 667 KiB

Open AccessShort Note

(4aS,5S,6aR,10aR,10bR)-5-Methoxy-9,9-dimethyl-4a,5,6a,7,10a,10b-hexahydro-12H-[1,3]dioxino[4′,5′:5,6]pyrano[4,3-b][1,2,3]triazolo[1,5-d][1,4]oxazine

by Leticia Lomas Romero, Guillermo E. Negron Silva, Ricardo Corona-Sánchez, Elsie Ramírez-Domínguez, Atilano Gutiérrez-Carrillo and Alma Sánchez-Eleuterio

Molbank 2024, 2024(4), M1898; https://doi.org/10.3390/M1898 - 9 Oct 2024

Abstract

A new tetracyclic morpholine-fused[5,1-c]-triazole, (4aS,5S,6aR,10aR,10bR)-5-methoxy-9,9-dimethyl-4a,5,6a,7,10a,10b-hexahydro-12H-[1,3]dioxino[4′,5′:5,6]pyrano[4,3-b][1,2,3]triazolo[1,5-d][1,4]oxazine, was synthesized via a five-step sequence starting from methyl α-_D-glucopyranoside by using, as a key step, an intramolecular copper(I) catalyzed alkyne-azide cycloaddition (CuAAC). The synthesized compound was fully characterized by ¹H and ¹³C NMR, FT-IR, and HRMS. Full article

(This article belongs to the Section Organic Synthesis)

► Show Figures

Figure 1

8 pages, 1467 KiB

Open AccessShort Note

2-(Butylamino)-6-chloro-4-[3-(7-chloro-4-quinolylamino)propylamino]-1,3,5-triazine

by Zimo Ren, Yuzhu Guo, Yang Xiao, Alessandra Gianoncelli, Paolo Coghi and Giovanni Ribaudo

Molbank 2024, 2024(4), M1895; https://doi.org/10.3390/M1895 - 8 Oct 2024

Abstract

We herein report the synthesis of a 7-chloro-aminoquinoline triazine conjugate. The s-triazine library was generated by stepwise nucleophilic substitution of cyanuric chloride with butylamine. The structure of the compound was comprehensively determined using various analytical techniques, including proton nuclear magnetic resonance (¹ [...] Read more.

We herein report the synthesis of a 7-chloro-aminoquinoline triazine conjugate. The s-triazine library was generated by stepwise nucleophilic substitution of cyanuric chloride with butylamine. The structure of the compound was comprehensively determined using various analytical techniques, including proton nuclear magnetic resonance (¹H NMR), carbon-13 nuclear magnetic resonance (¹³C NMR), heteronuclear single quantum coherence (HSQC), and Distortionless Enhancement by Polarization Transfer (DEPT-135) experiments. Additionally, ultraviolet (UV) spectroscopy, Fourier-transform infrared (FTIR) spectroscopy, and high-resolution mass spectrometry (HRMS) were employed for full characterization. Preliminary studies explored the potential interaction of the molecule with dihydrofolate reductase (DHFR) using molecular modeling. Furthermore, its drug-likeness was assessed by predicting relevant pharmacokinetic properties. Full article

► Show Figures

Figure 1

5 pages, 805 KiB

Open AccessShort Note

5-Diethoxymethyl-1,1-diethoxy-5-hydroxyundeca-3,6-diyn-2-one

by Ludvik O. Espeland and Leiv K. Sydnes

Molbank 2024, 2024(4), M1896; https://doi.org/10.3390/M1896 - 8 Oct 2024

Abstract

As an extension of our study of the reactivity of derivatives of 3,3,4,4-tetraethoxybut-1-yne, attempts have been made to achieve acid-catalyzed deacetalization of the diethoxymethyl moieties in 5-diethoxymethyl-1,1,2,2-tetraethoxyundeca-3,6-diyn-5-ol. That was not achieved; instead, only deketalization occurred and afforded the title compound, indicating that the [...] Read more.

As an extension of our study of the reactivity of derivatives of 3,3,4,4-tetraethoxybut-1-yne, attempts have been made to achieve acid-catalyzed deacetalization of the diethoxymethyl moieties in 5-diethoxymethyl-1,1,2,2-tetraethoxyundeca-3,6-diyn-5-ol. That was not achieved; instead, only deketalization occurred and afforded the title compound, indicating that the triple bond activates the propargylic diethoxy moiety relative to the other acetal groups. Full article

► Show Figures

Scheme 1

4 pages, 810 KiB

Open AccessShort Note

4-(1H-Tetrazol-5-yl)-2-(p-tolyl)quinoline

by Angelika Lásiková and Daniel Végh

Molbank 2024, 2024(4), M1897; https://doi.org/10.3390/M1897 - 8 Oct 2024

Abstract

The synthesis of 4-(1H-tetrazol-5-yl)-2-(p-tolyl)quinoline 4 as a possible modification of the biphenyltetrazole substructure of losartan 1 is described. The transformation of 2-(p-tolyl)quinoline-4-carbonitrile 3 to the corresponding tetrazole 4 was carried out by the reaction of trimethysilyl azide [...] Read more.

The synthesis of 4-(1H-tetrazol-5-yl)-2-(p-tolyl)quinoline 4 as a possible modification of the biphenyltetrazole substructure of losartan 1 is described. The transformation of 2-(p-tolyl)quinoline-4-carbonitrile 3 to the corresponding tetrazole 4 was carried out by the reaction of trimethysilyl azide and dibutyltin oxide as a catalyst in refluxing toluene. The title compound (4) was characterized by IR, ¹H NMR, ¹³C NMR, and HRMS. Full article

(This article belongs to the Section Organic Synthesis)

► Show Figures

Figure 1

5 pages, 1384 KiB

Open AccessCommunication

Synthesis of Novel Thiazoles Based on (+)-Usnic Acid

by Aleksandr S. Filimonov, Olga A. Luzina and Nariman F. Salakhutdinov

Molbank 2024, 2024(4), M1894; https://doi.org/10.3390/M1894 - 3 Oct 2024

Abstract

A series of usnic acid derivatives containing a thiazole ring with an amide substituent were synthesized. The convenient method for synthesis of these compounds is a reaction of 14-bromousnic acid with N-acylthioureas. Acylation of aminothiazole does not lead to the targeted compound. Full article

► Show Figures

Figure 1

6 pages, 1788 KiB

Open AccessShort Note

Benzo[d][1,3]oxathiole-2-thione

by R. Alan Aitken, David B. Cordes, Lauryne Cottineau and Aidan P. McKay

Molbank 2024, 2024(4), M1891; https://doi.org/10.3390/M1891 - 30 Sep 2024

Abstract

Although known for 120 years, the title compound has not been adequately characterised before. In this paper, it is fully characterised by ¹H and ¹³C NMR and IR spectroscopy and its X-ray structure has been determined for the first time. Full article

(This article belongs to the Section Structure Determination)

► Show Figures

Graphical abstract

13 pages, 6421 KiB

Open AccessShort Note

[(2-Chlorophenyl)-(4-fluorophenyl)methylene]-(4-fluorophenyl)amine

by Salvador Vilchis-Valdés, Alberto Cedillo-Cruz, Marco A. García-Eleno, Diego Martínez-Otero and Erick Cuevas-Yañez

Molbank 2024, 2024(4), M1892; https://doi.org/10.3390/M1892 - 30 Sep 2024

Abstract

The formation of a N,1,1-triaryl imine derived from (2-chlorophenyl)-bis-(4-fluorophenyl)methanol is reported. The title compound is formed from a consecutive process which involves a nucleophilic substitution and subsequent Schmidt reaction. A description of the synthesized compound’s NMR spectra is presented and the structure [...] Read more.

The formation of a N,1,1-triaryl imine derived from (2-chlorophenyl)-bis-(4-fluorophenyl)methanol is reported. The title compound is formed from a consecutive process which involves a nucleophilic substitution and subsequent Schmidt reaction. A description of the synthesized compound’s NMR spectra is presented and the structure was unambiguously established by X-ray analysis. A Hirshfeld surface analysis is also included, confirming the presence of intermolecular H···F interactions involved in crystal packing. Full article

► Show Figures

Figure 1

5 pages, 402 KiB

Open AccessShort Note

rac-2-(2′-Ferrocenyl-2′-hydroxy-n-propyl)-1,3-benzothiazole

by Martin G. Zhen, Kathleen L. May and Robert A. Gossage

Molbank 2024, 2024(4), M1893; https://doi.org/10.3390/M1893 - 30 Sep 2024

Abstract

The synthesis and characterisation (UV-Vis, IR, HRESI-MS, ¹H and ¹³C NMR spectroscopies, electrochemistry) is reported of the novel title material (1: alternatively named rac-1-(2′-benzothiazolyl)-2-ferrocenyl-2-propanol): a rare example of a ferrocenyl-benzothiazole hybrid species. Compound 1 is produced by the [...] Read more.

The synthesis and characterisation (UV-Vis, IR, HRESI-MS, ¹H and ¹³C NMR spectroscopies, electrochemistry) is reported of the novel title material (1: alternatively named rac-1-(2′-benzothiazolyl)-2-ferrocenyl-2-propanol): a rare example of a ferrocenyl-benzothiazole hybrid species. Compound 1 is produced by the low temperature reaction of acetylferrocene (3) with a solution of the methyl anion derived via the deprotonation of 2-methyl-1,3-benzothiazole. The yield of 1 is moderate (34%) after purification and is an air and thermally stable solid under ambient conditions. Attempts to sublime 1, however, result in decomposition with one of the products being identified (NMR) as 3. The spectroscopic features of 1 are presented. Attempts to obtain suitable crystalline material of 1 for a single crystal X-ray diffraction study were unfortunately unsuccessful. Compound 1 also does not form stable coordination complexes with various metal salts (e.g., Ni[2+], Co[2+], etc.) under the conditions tested. Full article

(This article belongs to the Section Organic Synthesis)

► Show Figures

Scheme 1

6 pages, 1727 KiB

Open AccessShort Note

(R)-2-Amino-1-hydroxyethylphosphonic Acid

by Majid Motevalli, Isaac Abrahams, Peter Blakskjær, Caroline E. Wyatt and Peter B. Wyatt

Molbank 2024, 2024(4), M1888; https://doi.org/10.3390/M1888 - 26 Sep 2024

Abstract

(R)-2-Amino-1-hydroxyethylphosphonic acid 2 was prepared by hydrolytic kinetic resolution of rac-diethyl oxiran-2-ylphosphonate followed by reaction with benzylamine, acid hydrolysis, catalytic hydrogenolysis, and anion-exchange chromatography. Recrystallization from water-ethanol gave pure 2, which was characterized by IR, ¹H NMR, ¹³ [...] Read more.

(R)-2-Amino-1-hydroxyethylphosphonic acid 2 was prepared by hydrolytic kinetic resolution of rac-diethyl oxiran-2-ylphosphonate followed by reaction with benzylamine, acid hydrolysis, catalytic hydrogenolysis, and anion-exchange chromatography. Recrystallization from water-ethanol gave pure 2, which was characterized by IR, ¹H NMR, ¹³C NMR, ³¹P NMR, polarimetry, elemental microanalysis, high-resolution mass spectrometry, and single-crystal X-ray diffraction. The acid 2 crystallized in the orthorhombic noncentrosymmetric space group P2₁2₁2₁ with cell parameters a = 6.303 (2) Å, b = 7.104 (2) Å, c = 11.627 (3) Å. The X-ray crystal structure confirmed the (R)-configuration of 2 and revealed that 2 is zwitterionic in the solid state, with extensive intermolecular hydrogen bonding between the hydroxyl, ammonium cation, and phosphonate anion groups. Full article

► Show Figures

Graphical abstract

8 pages, 2371 KiB

Open AccessShort Note

Bis [4,4′-(1,3-Phenylenebis(azanylylidene))-bis(3,6-di-tert-butyl-2-oxycyclohexa-2,5-dien-1-one)-bis(dimethylsulfoxide)nickel(II)]

by Irina N. Meshcheryakova, Nikolay O. Druzhkov, Ilya A. Yakushev, Kseniya V. Arsenyeva, Anastasiya V. Klimashevskaya and Alexandr V. Piskunov

Molbank 2024, 2024(4), M1890; https://doi.org/10.3390/M1890 - 26 Sep 2024

Abstract

A new cage-like dimeric nickel(II) complex Ni₂L₂(DMSO)₄ based on a ditopic redox-active hydroxy-para-iminobenzoquinone type ligand LH₂ (L is 4,4′-(1,3-phenylene-bis(azaneylylidene))-bis(3,6-di-tert-butyl-2-oxycyclohexa-2,5-dien-1-one dianion) was synthesized in DMSO at 120 °C. The molecular structure of [...] Read more.

A new cage-like dimeric nickel(II) complex Ni₂L₂(DMSO)₄ based on a ditopic redox-active hydroxy-para-iminobenzoquinone type ligand LH₂ (L is 4,4′-(1,3-phenylene-bis(azaneylylidene))-bis(3,6-di-tert-butyl-2-oxycyclohexa-2,5-dien-1-one dianion) was synthesized in DMSO at 120 °C. The molecular structure of the synthesized compound was determined by X-ray diffraction analysis. The complex Ni₂L₂(DMSO)₄ is almost insoluble in all organic solvents, probably due to the presence of a large number of intermolecular contacts in its structure. The electronic spectrum and thermal stability of the crystalline compound have been studied. Full article

► Show Figures

Figure 1

6 pages, 932 KiB

Open AccessShort Note

Methyl 6,7-Difluoro-2-[(4-fluorobenzyl)sulfanyl]-4-hydroxyquinoline-3-carboxylate

by Vladimir A. Potapov, Irina A. Novokshonova, Maxim V. Musalov, Svetlana V. Amosova and Oleg A. Rakitin

Molbank 2024, 2024(4), M1889; https://doi.org/10.3390/M1889 - 26 Sep 2024

Abstract

A convenient synthesis of a novel fluoroquinolone precursor, methyl 6,7-difluoro-2-[(4-fluorobenzyl)sulfanyl]-4-hydroxyquinoline-3-carboxylate, at a 78% yield starting from 3,4-difluorophenyl isothiocyanate was developed. The structure of the product was established by ¹H, ¹³C, and ¹⁹F NMR spectroscopy, mass spectrometry, IR spectroscopy and confirmed [...] Read more.

A convenient synthesis of a novel fluoroquinolone precursor, methyl 6,7-difluoro-2-[(4-fluorobenzyl)sulfanyl]-4-hydroxyquinoline-3-carboxylate, at a 78% yield starting from 3,4-difluorophenyl isothiocyanate was developed. The structure of the product was established by ¹H, ¹³C, and ¹⁹F NMR spectroscopy, mass spectrometry, IR spectroscopy and confirmed by elemental analysis. The title compound, containing the pharmacophoric 4-fluorobenzyl group, will be used in the synthesis of novel fluoroquinolone derivatives. Full article

(This article belongs to the Section Organic Synthesis)

► Show Figures

Figure 1

5 pages, 1385 KiB

Open AccessShort Note

Ac-[K-Aib-C(3,9-Acm; 6,12-DFLC₍_Acm₎KKESEK)]₄-NH₂

by Vasiliki Moulasioti, Evgenia Fotou, Vassilios Moussis and Vassilios Tsikaris

Molbank 2024, 2024(4), M1887; https://doi.org/10.3390/M1887 - 25 Sep 2024

Abstract

Chemoselective reactions have played a crucial role in the development of high-molecular-weight (>3000 Da) macromolecules with a branched architecture, particularly as peptides and epitope-based vaccines have emerged as promising tools for drug development. Based on this, in this study, we designed and synthesized [...] Read more.

Chemoselective reactions have played a crucial role in the development of high-molecular-weight (>3000 Da) macromolecules with a branched architecture, particularly as peptides and epitope-based vaccines have emerged as promising tools for drug development. Based on this, in this study, we designed and synthesized the peptide macromolecule CH₃CO-[K-Aib-C(3,9-CH₂NHCOCH₃; 6,12-DFLC(CH₂NHCOCH₃)KKESEK)]₄-NH₂ [Ac-K-Aib-C(3,9-Acm); 6,12-epitope)]₄-NH₂] using chemoselective thioether bond formation between the peptide carrier CPSOC (3,9 Acm) and the IAc-DFLC_(Acm)KKESEK-NH₂ peptide epitope. The conjugate was purified via RP-HPLC and characterized via HR-ESI-MS. The epitope D¹²⁸FLCKKESEK¹³⁷ derives from the lethal toxin, ammodytoxin A, from the V. ammodytes snake species, and it was synthesized using the SPPS Fmoc/tBu methodology and characterized via HR-ESI-MS and NMR techniques. Full article

► Show Figures

Figure 1

5 pages, 1538 KiB

Open AccessCommunication

Synthesis and Characterization of N-Nitroso-3-morpholinosydnonimine as NO Radical Donor

by Nathalie Saffon-Merceron, Christian Lherbet and Pascal Hoffmann

Molbank 2024, 2024(4), M1886; https://doi.org/10.3390/M1886 - 24 Sep 2024

Abstract

N-Nitroso-3-morpholinosydnonimine 3 was prepared by nitrosation of SIN-1 and characterized by ¹H-NMR, ¹³C-NMR, and HRMS. Its structure, confirmed by single crystal X-ray diffraction analysis, was found to be in agreement with its mesoionic and aromatic character. Unlike 3-morpholino-sydnonimine (SIN-1), which [...] Read more.

N-Nitroso-3-morpholinosydnonimine 3 was prepared by nitrosation of SIN-1 and characterized by ¹H-NMR, ¹³C-NMR, and HRMS. Its structure, confirmed by single crystal X-ray diffraction analysis, was found to be in agreement with its mesoionic and aromatic character. Unlike 3-morpholino-sydnonimine (SIN-1), which releases both nitric oxide and superoxide radical, decomposition of this nitrosylated sydonimine could yield nitric oxide as the only decomposition product, and thus without the formation of toxic peroxynitrite. Full article

(This article belongs to the Section Organic Synthesis)

► Show Figures

Figure 1

6 pages, 1319 KiB

Open AccessShort Note

2-Methylpropan-2-ammonium [(3R,5R)-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-[(2S)-2-methylbutanoyl]oxy-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-heptanoate

by Ioana-Georgeta Grosu, Alexandru Turza, Xenia Filip and Maria-Olimpia Miclaus

Molbank 2024, 2024(3), M1885; https://doi.org/10.3390/M1885 - 24 Sep 2024

Abstract

Pravastatin is a popular statin agent with applications in the treatment of cardiovascular diseases for patients with an abnormal lipid panel. The starting form of pravastatin is amorphous and following recrystallization, it becomes a crystalline solid with tert-butylamine salt molecules embedded within the [...] Read more.

Pravastatin is a popular statin agent with applications in the treatment of cardiovascular diseases for patients with an abnormal lipid panel. The starting form of pravastatin is amorphous and following recrystallization, it becomes a crystalline solid with tert-butylamine salt molecules embedded within the lattice. Its molecular and crystal structure were elucidated based on single-crystal X-ray diffraction and characterized by ss-NMR. Full article

(This article belongs to the Section Structure Determination)

► Show Figures

Figure 1

8 pages, 981 KiB

Open AccessShort Note

4-(10-Phenyl-9-Anthracenyl)-1,2-Benzenediol

by Nicola Edwards and Kelsey Harris

Molbank 2024, 2024(3), M1884; https://doi.org/10.3390/M1884 - 23 Sep 2024

Abstract

The title compound, 4-(10-phenyl-9-anthracenyl)-1,2-benzenediol, was synthesized using a two-step protocol. In the first step, 9-phenyl,10-bromoanthracene was coupled to 3,4-dimethoyphenylboronic acid by employing Pd(PPh₃)₄ as the catalyst and potassium carbonate as the base. Methoxy group removal was effected using HBr in [...] Read more.

The title compound, 4-(10-phenyl-9-anthracenyl)-1,2-benzenediol, was synthesized using a two-step protocol. In the first step, 9-phenyl,10-bromoanthracene was coupled to 3,4-dimethoyphenylboronic acid by employing Pd(PPh₃)₄ as the catalyst and potassium carbonate as the base. Methoxy group removal was effected using HBr in the presence of acetic acid in the second step. Overall, two novel 9,10-diphenylanthracence-based compounds were synthesized in this work; standard spectroscopic techniques and high-resolution mass spectrometry were employed in their characterization. The photophysical properties of these compounds are also reported. These compounds are potentially useful as sensors, catalysts and building blocks for larger architectures. Full article

► Show Figures

Figure 1

6 pages, 1036 KiB

Open AccessCommunication

Thiazolylketol Acetates as Glycosyl Donors: Stereoselective Synthesis of a C-Ketoside

by Clark Ferrari, Alessandro Dondoni and Alberto Marra

Molbank 2024, 2024(3), M1883; https://doi.org/10.3390/M1883 - 23 Sep 2024

Abstract

We have already proven that thiazolylketol acetates, synthetised by addition of 2-lithiothiazole to sugar lactones followed by acetylation, are efficient glycosyl donors in the presence of O-, N-, and P-nucleophiles. We describe here their first use in the C-glycosidation using [...] Read more.

We have already proven that thiazolylketol acetates, synthetised by addition of 2-lithiothiazole to sugar lactones followed by acetylation, are efficient glycosyl donors in the presence of O-, N-, and P-nucleophiles. We describe here their first use in the C-glycosidation using trimetylsilyl cyanide as the acceptor in order to prepare, after thiazole-to-formyl unmasking and reduction, the corresponding C-ketosides. Full article

(This article belongs to the Section Organic Synthesis)

► Show Figures

Graphical abstract

7 pages, 243 KiB

Open AccessCommunication

The Effects of Ceric Ammonium Nitrate in the Oxidation of 2-Benzyl-1,4-dimethoxybenzene Derivatives

by Marcello Casertano, Anna Aiello, Marialuisa Menna and Concetta Imperatore

Molbank 2024, 2024(3), M1882; https://doi.org/10.3390/M1882 - 16 Sep 2024

Abstract

The one- or two-electron reduction in quinone compounds gives rise to semiquinones and hydroquinones, respectively, which, in turn, can be oxidized back to quinones, generating a cyclic redox system with the production of reactive oxygen species (ROS). For these reasons, quinone derivatives participate [...] Read more.

The one- or two-electron reduction in quinone compounds gives rise to semiquinones and hydroquinones, respectively, which, in turn, can be oxidized back to quinones, generating a cyclic redox system with the production of reactive oxygen species (ROS). For these reasons, quinone derivatives participate in various biological processes in metabolic pathways, such as oxidative reactions and electron transport. In addition, natural quinone compounds as well as their semisynthetic and/or synthetically produced derivatives are of great pharmacological interest for the discovery and design of new drugs. As a result, their chemical reactivity as well as new methods for their synthesis are being investigated on an ongoing basis. Herein, a mild and efficient synthesis to obtain 2-(4-benzyl substituted)-1,4-dimethoxybenzene derivatives is reported. In addition, an evaluation of the effects on the quinone/diquinone ratio in the reaction product in relation to different ways of adding the oxidant CAN to the arene solution is discussed. Full article

(This article belongs to the Section Organic Synthesis)

► Show Figures

Scheme 1

4 pages, 586 KiB

Open AccessShort Note

rel-(2R,3S)-2-((Diphenylmethylene)amino)-5-oxo-5-phenyl-3-(thiophen-2-yl)pentanenitrile

by Donka N. Tasheva and Vesela M. Mihaylova

Molbank 2024, 2024(3), M1881; https://doi.org/10.3390/M1881 - 11 Sep 2024

Abstract

The reaction of 2-((diphenylmethylene)amino)acetonitrile with (E)-1-phenyl-3-(thiophen-2-yl)prop-2-en-1-one was performed by using 33% NaOH in CH₃CN for 30 min at 0 °C. The main product—rel-(2R,3S)-2-((diphenylmethylene)amino)-5-oxo-5-phenyl-3-(thiophen-2-yl)pentanenitrile—was isolated and characterized by IR, ¹H NMR, ¹³C NMR, ¹H-¹H COSY, and high-resolution mass spectrometry (HRMS). Full article

(This article belongs to the Section Organic Synthesis)

► Show Figures

Graphical abstract

Journal Description

Molbank

Latest Articles

Journal Menu

Journal Browser

Highly Accessed Articles

Latest Books

E-Mail Alert

News

Topics

Conferences

Special Issues

Topical Collections

Further Information

Guidelines

MDPI Initiatives

Follow MDPI