Multicomponent Synthesis of 2-(2,4-Diamino-3-cyano-5<i>H</i>-chromeno[2,3-<i>b</i>]pyridin-5-yl)malonic Acids in DMSO

Dimethyl sulfoxide is a widely used solvent in organic synthesis and in the pharmaceutical industry because of its low cost, stability, and low toxicity. Multicomponent reactions are an advanced approach that has become an efficient, economical, and eco-friendly substitute for the conventional seque...

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Autores principales:	Yuliya E. Ryzhkova, Michail N. Elinson, Oleg I. Maslov, Artem N. Fakhrutdinov
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	salicylaldehyde malononitrile dimer malonic acid chromeno[2,3-<i>b</i>]pyridine multicomponent reactions dimethyl sulfoxide Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/f3cfe1a1d84b4d368e453ce479fc8c3c
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spelling	oai:doaj.org-article:f3cfe1a1d84b4d368e453ce479fc8c3c2021-11-25T18:27:38ZMulticomponent Synthesis of 2-(2,4-Diamino-3-cyano-5<i>H</i>-chromeno[2,3-<i>b</i>]pyridin-5-yl)malonic Acids in DMSO10.3390/molecules262268391420-3049https://doaj.org/article/f3cfe1a1d84b4d368e453ce479fc8c3c2021-11-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/22/6839https://doaj.org/toc/1420-3049Dimethyl sulfoxide is a widely used solvent in organic synthesis and in the pharmaceutical industry because of its low cost, stability, and low toxicity. Multicomponent reactions are an advanced approach that has become an efficient, economical, and eco-friendly substitute for the conventional sequential multi-step synthesis of various biologically active compounds. This approach was adopted for the synthesis of previously unknown 2-(2,4-diamino-3-cyano-5<i>H</i>-chromeno[2,3-<i>b</i>]pyridin-5-yl)malonic acids via transformation of salicylaldehydes, malononitrile dimer, and malonic acid. It was shown that the use of DMSO at room temperature makes it possible to synthesize previously unavailable compounds. The investigation of the reaction mechanism using <sup>1</sup>H-NMR monitoring made it possible to confirm the proposed mechanism of the transformation. The structure of synthesized 5<i>H</i>-chromeno[2,3-<i>b</i>]pyridines was confirmed by 2D-NMR spectroscopy.Yuliya E. RyzhkovaMichail N. ElinsonOleg I. MaslovArtem N. FakhrutdinovMDPI AGarticlesalicylaldehydemalononitrile dimermalonic acidchromeno[2,3-<i>b</i>]pyridinemulticomponent reactionsdimethyl sulfoxideOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6839, p 6839 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	salicylaldehyde malononitrile dimer malonic acid chromeno[2,3-<i>b</i>]pyridine multicomponent reactions dimethyl sulfoxide Organic chemistry QD241-441
spellingShingle	salicylaldehyde malononitrile dimer malonic acid chromeno[2,3-<i>b</i>]pyridine multicomponent reactions dimethyl sulfoxide Organic chemistry QD241-441 Yuliya E. Ryzhkova Michail N. Elinson Oleg I. Maslov Artem N. Fakhrutdinov Multicomponent Synthesis of 2-(2,4-Diamino-3-cyano-5<i>H</i>-chromeno[2,3-<i>b</i>]pyridin-5-yl)malonic Acids in DMSO
description	Dimethyl sulfoxide is a widely used solvent in organic synthesis and in the pharmaceutical industry because of its low cost, stability, and low toxicity. Multicomponent reactions are an advanced approach that has become an efficient, economical, and eco-friendly substitute for the conventional sequential multi-step synthesis of various biologically active compounds. This approach was adopted for the synthesis of previously unknown 2-(2,4-diamino-3-cyano-5<i>H</i>-chromeno[2,3-<i>b</i>]pyridin-5-yl)malonic acids via transformation of salicylaldehydes, malononitrile dimer, and malonic acid. It was shown that the use of DMSO at room temperature makes it possible to synthesize previously unavailable compounds. The investigation of the reaction mechanism using <sup>1</sup>H-NMR monitoring made it possible to confirm the proposed mechanism of the transformation. The structure of synthesized 5<i>H</i>-chromeno[2,3-<i>b</i>]pyridines was confirmed by 2D-NMR spectroscopy.
format	article
author	Yuliya E. Ryzhkova Michail N. Elinson Oleg I. Maslov Artem N. Fakhrutdinov
author_facet	Yuliya E. Ryzhkova Michail N. Elinson Oleg I. Maslov Artem N. Fakhrutdinov
author_sort	Yuliya E. Ryzhkova
title	Multicomponent Synthesis of 2-(2,4-Diamino-3-cyano-5<i>H</i>-chromeno[2,3-<i>b</i>]pyridin-5-yl)malonic Acids in DMSO
title_short	Multicomponent Synthesis of 2-(2,4-Diamino-3-cyano-5<i>H</i>-chromeno[2,3-<i>b</i>]pyridin-5-yl)malonic Acids in DMSO
title_full	Multicomponent Synthesis of 2-(2,4-Diamino-3-cyano-5<i>H</i>-chromeno[2,3-<i>b</i>]pyridin-5-yl)malonic Acids in DMSO
title_fullStr	Multicomponent Synthesis of 2-(2,4-Diamino-3-cyano-5<i>H</i>-chromeno[2,3-<i>b</i>]pyridin-5-yl)malonic Acids in DMSO
title_full_unstemmed	Multicomponent Synthesis of 2-(2,4-Diamino-3-cyano-5<i>H</i>-chromeno[2,3-<i>b</i>]pyridin-5-yl)malonic Acids in DMSO
title_sort	multicomponent synthesis of 2-(2,4-diamino-3-cyano-5<i>h</i>-chromeno[2,3-<i>b</i>]pyridin-5-yl)malonic acids in dmso
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/f3cfe1a1d84b4d368e453ce479fc8c3c
work_keys_str_mv	AT yuliyaeryzhkova multicomponentsynthesisof224diamino3cyano5ihichromeno23ibipyridin5ylmalonicacidsindmso AT michailnelinson multicomponentsynthesisof224diamino3cyano5ihichromeno23ibipyridin5ylmalonicacidsindmso AT olegimaslov multicomponentsynthesisof224diamino3cyano5ihichromeno23ibipyridin5ylmalonicacidsindmso AT artemnfakhrutdinov multicomponentsynthesisof224diamino3cyano5ihichromeno23ibipyridin5ylmalonicacidsindmso
_version_	1718411171656105984

Multicomponent Synthesis of 2-(2,4-Diamino-3-cyano-5<i>H</i>-chromeno[2,3-<i>b</i>]pyridin-5-yl)malonic Acids in DMSO

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