Synthesis of alkylated carbonyl‐bearing furans via acid‐catalyzed Friedel‐Crafts reaction DOI Open Access
I. M. Tkachenko, Н. А. Иванова, Kristina S. Khrapovitskaya

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 11, 2024

Abstract Carbonyl‐bearing furans, certain pyrroles, and thiophenes were alkylated using alcohols in an acidic medium. Some 5‐alkylated derivatives of 2‐furoic acid with various adamantyls‐, cycloalkyl‐, other 2°‐ 3°‐alkyl substituents synthesized as a biomass‐derived chemical platform. Side reaction resulted the substitution carboxylic group, leading to formation 1,5‐dialkyl furans. In alkylation acyl formyl furan, either mono‐ or di‐alkyl products obtained, depending on functional group present furan nucleus. Pyrroles (or thiophenes) related groups exclusively near‐exclusively) yielded mono‐alkyl products. The resultant 5‐substituted carbonyl furans can be used building blocks synthetic equivalents for 1 C 4 synthons, demonstrated by series reactions involving 5‐adamantan‐1‐yl‐2‐furoic acid.

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,

A. 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