1,3-Dipolar Cycloaddition of Nitrile Oxides and Nitrilimines to (−)-β-Caryophyllene: Stereoselective Synthesis of Polycyclic Derivatives and Their Biological Testing DOI Open Access

Dmitry E. Shybanov,

Maxim E. Kukushkin, Yuri K. Grishin

et al.

International Journal of Molecular Sciences, Journal Year: 2024, Volume and Issue: 25(21), P. 11435 - 11435

Published: Oct. 24, 2024

The cycloaddition of nitrile oxides and nitrilimines to one or both the C=C double bonds caryophyllene is described. possibility introducing five-membered fused spiro-linked heterocycles into structure sesquiterpenes by 1,3-dipolar reactions was demonstrated. As a result these reactions, pharmacophore fragments isoxazoline pyrazoline are introduced caryophyllene, which leads an increase in conformational rigidity molecule. A complete stereochemical assignment adducts carried out. study antiviral cytotoxic activity for some heterocyclic derivatives synthesized this work revealed relatively high biological previously little-studied at exocyclic C=CH

Language: Английский

4-Alkyl-4H-thieno[2′,3′:4,5]pyrrolo[2,3-b]quinoxaline Derivatives as New Heterocyclic Analogues of Indolo[2,3-b]quinoxalines: Synthesis and Antitubercular Activity DOI Open Access

Gusein A. o. Sadykhov,

Danila V. Belyaev,

Ekaterina E. Khramtsova

et al.

International Journal of Molecular Sciences, Journal Year: 2025, Volume and Issue: 26(1), P. 369 - 369

Published: Jan. 3, 2025

The synthetic approach based on a sequence of Buchwald–Hartwig cross-coupling and annulation through intramolecular oxidative cyclodehydrogenation has been used for the construction novel 4-alkyl-4H-thieno[2′,3′:4,5]pyrrolo[2,3-b]quinoxaline derivatives. For first time, these polycyclic compounds were evaluated antimycobacterial activity, including extensively drug-resistant strains. A reasonable bacteriostatic effect against Mycobacterium tuberculosis H37Rv was demonstrated. plausible mechanism activity heterocyclic analogues indolo[2,3-b]quinoxalines advanced basis their molecular docking data.

Language: Английский

Citations

0

ANRORC type rearrangement/intermolecular cyclocondensation cascade of 5,6-dicyano-3-(2-oxo-2-ethyl)pyrazin-2(1H)-ones with hydrazine hydrate for the synthesis of 2-(pyrazol-3-yl)imidazo[4,5-d]pyridazines DOI
В. А. Мамедов,

Venera R. Galimullina,

Zheng‐Wang Qu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A novel ANRORC type rearrangement/intermolecular cyclocondensation cascade of 5,6-dicyano-3-(2-oxo-2-ethyl)pyrazin-2(1 H )-ones with hydrazine hydrate is disclosed, providing an efficient strategy synthesizing 2-(pyrazol-3-yl)imidazo[4,5- d ]pyridazines.

Language: Английский

Citations

0

A Universal Method for the Synthesis of new Heterocyclic Systems: Pyrimido[2,1‐f][1,2,4]triazines DOI Creative Commons
Samvel N. Sirakanyan, Domenico Spinelli, Athina Geronikaki

et al.

ChemistryOpen, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 31, 2025

The synthesis of pyrimido[2,1-f][1,2,4]triazines was performed in four steps. Compounds obtained by acylation the starting amino esters thieno[2,3-b]pyridines were reacted with various amines. resulting derivatives underwent cyclization presence hydrazine hydrate leading to new aminomethyl thieno[3,2-d]pyrimidines. Further latter resulted unique heterocyclic systems: pyrido[3'',2'':4',5']thieno[3',2':4,5]pyrimido[2,1-f][1,2,4]triazines. uniqueness these systems lies fact that even combination last two cycles represents a system.

Language: Английский

Citations

0

New thiosemicarbazones possessing activity against SARS-CoV-2 and H1N1 influenza viruses DOI

Olga A. Zhupikova,

Оlga I. Yarovaya, Mariya K. Marenina

et al.

Mendeleev Communications, Journal Year: 2025, Volume and Issue: 35(2), P. 145 - 147

Published: Jan. 1, 2025

Language: Английский

Citations

0

Asymmetric Synthesis of Isoindolin-1-ones from Enamides via Pd-Catalyzed Intramolecular Reductive Heck Reaction DOI
М. А. Ashatkina,

D.I. Shamshina,

Vadim A. Shiryaev

et al.

Russian Journal of General Chemistry, Journal Year: 2025, Volume and Issue: 95(1), P. 30 - 34

Published: Jan. 1, 2025

Language: Английский

Citations

0

Reactions of acetylenes with substituted 2 H -thiopyran-2-thiones and their isoelectronic analogues: difficult choice of optimal route DOI
Константин Ф. Суздалев, Михаил Е. Клецкий, Антон В. Лисовин

et al.

Journal of Sulfur Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 15

Published: March 10, 2025

Language: Английский

Citations

0

Synthesis of Functionalized 1H-Imidazoles via Denitrogenative Transformation of 5-Amino-1,2,3-Triazoles DOI Creative Commons
Pavel S. Gribanov, Anna N. Philippova, Alexander F. Smol’yakov

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(7), P. 1401 - 1401

Published: March 21, 2025

An efficient access to novel 2-substituted 1H-imidazole derivatives was developed based on acid-mediated denitrogenative transformation of 5-amino-1,2,3-triazole available through dipolar azide−nitrile cycloaddition (DCR). The proposed approach includes intramolecular cyclization 5-amino-4-aryl-1-(2,2-diethoxyethyl) 1,2,3-triazoles followed by triazole ring opening and insertion in situ formed carbene intermediate into the O-H bond different alcohols under acidic conditions.

Language: Английский

Citations

0

Assembly of phenylaminopyrrolo[1,2-a]pyrazinium salts from N-allenylpyrrole-2-carbaldehydes and phenylhydrazine in the presence of acids DOI
Elena A. Gyrgenova,

S. V. Martynovskaya,

Igor Ushakov

et al.

Russian Chemical Bulletin, Journal Year: 2025, Volume and Issue: 74(1), P. 143 - 150

Published: Jan. 1, 2025

Language: Английский

Citations

0

Recent advances in chemistry of β-cyano ketones DOI
Nicolai A. Aksenov, Дмитрий А. Аксенов,

Alexander E. Kurlikov

et al.

Russian Chemical Bulletin, Journal Year: 2025, Volume and Issue: 74(2), P. 305 - 327

Published: Feb. 1, 2025

Language: Английский

Citations

0

Thiol-Epoxy Click Chemistry: The Synthesis of Vicinal Amino Alcohols Containing a 1,2,4-Triazole Ring DOI Creative Commons
Artyom V. Petrosyan, Astghik A. Shahkhatuni,

Andranik M. Davinyan

et al.

Chemistry, Journal Year: 2025, Volume and Issue: 7(2), P. 53 - 53

Published: April 1, 2025

As examples of “Click Chemistry”, the reaction 1-(oxiran-2-ylmethyl)piperidine with several 1,2,4-triazoles derivatives was studied. a result, shows that oxirane ring opens regiospecifically, according to Krasusky’s rule, without using catalyst. The basic nitrogen present in has catalytic (anchimer) effect.

Language: Английский

Citations

0