Cargando…

A Facile and Catalyst-Free Microwave-Promoted Multicomponent Reaction for the Synthesis of Functionalised 1,4-Dihydropyridines With Superb Selectivity and Yields

We report a highly efficient green protocol for developing a novel library of 1,2,4-triazole-tagged 1,4-dihydropyridine analogs through the one-pot process from the four-component fusion of the 1H-1,2,4-triazol-3-amine with different chosen aldehydes, diethyl acetylenedicarboxylate, and active methy...

Descripción completa

Detalles Bibliográficos
Autores principales: Kerru, Nagaraju, Maddila, Suresh, Jonnalagadda, Sreekantha B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8044462/
https://www.ncbi.nlm.nih.gov/pubmed/33869142
http://dx.doi.org/10.3389/fchem.2021.638832
_version_ 1783678490797670400
author Kerru, Nagaraju
Maddila, Suresh
Jonnalagadda, Sreekantha B.
author_facet Kerru, Nagaraju
Maddila, Suresh
Jonnalagadda, Sreekantha B.
author_sort Kerru, Nagaraju
collection PubMed
description We report a highly efficient green protocol for developing a novel library of 1,2,4-triazole-tagged 1,4-dihydropyridine analogs through the one-pot process from the four-component fusion of the 1H-1,2,4-triazol-3-amine with different chosen aldehydes, diethyl acetylenedicarboxylate, and active methylene compounds in a water medium under microwave irradiation and catalyst-free conditions. Excellent yields (94–97%) of the target products were achieved with high selectivity with a short reaction time (<12 min) at room temperature. The structures of the synthesized pyrimidine analogs were established by NMR and HRMS spectroscopic analysis. Simple workup, impressive yields, no column chromatography, green solvent, rapid reaction, and excellent functional group tolerance are the benefits of this protocol.
format Online
Article
Text
id pubmed-8044462
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher Frontiers Media S.A.
record_format MEDLINE/PubMed
spelling pubmed-80444622021-04-15 A Facile and Catalyst-Free Microwave-Promoted Multicomponent Reaction for the Synthesis of Functionalised 1,4-Dihydropyridines With Superb Selectivity and Yields Kerru, Nagaraju Maddila, Suresh Jonnalagadda, Sreekantha B. Front Chem Chemistry We report a highly efficient green protocol for developing a novel library of 1,2,4-triazole-tagged 1,4-dihydropyridine analogs through the one-pot process from the four-component fusion of the 1H-1,2,4-triazol-3-amine with different chosen aldehydes, diethyl acetylenedicarboxylate, and active methylene compounds in a water medium under microwave irradiation and catalyst-free conditions. Excellent yields (94–97%) of the target products were achieved with high selectivity with a short reaction time (<12 min) at room temperature. The structures of the synthesized pyrimidine analogs were established by NMR and HRMS spectroscopic analysis. Simple workup, impressive yields, no column chromatography, green solvent, rapid reaction, and excellent functional group tolerance are the benefits of this protocol. Frontiers Media S.A. 2021-03-31 /pmc/articles/PMC8044462/ /pubmed/33869142 http://dx.doi.org/10.3389/fchem.2021.638832 Text en Copyright © 2021 Kerru, Maddila and Jonnalagadda. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Kerru, Nagaraju
Maddila, Suresh
Jonnalagadda, Sreekantha B.
A Facile and Catalyst-Free Microwave-Promoted Multicomponent Reaction for the Synthesis of Functionalised 1,4-Dihydropyridines With Superb Selectivity and Yields
title A Facile and Catalyst-Free Microwave-Promoted Multicomponent Reaction for the Synthesis of Functionalised 1,4-Dihydropyridines With Superb Selectivity and Yields
title_full A Facile and Catalyst-Free Microwave-Promoted Multicomponent Reaction for the Synthesis of Functionalised 1,4-Dihydropyridines With Superb Selectivity and Yields
title_fullStr A Facile and Catalyst-Free Microwave-Promoted Multicomponent Reaction for the Synthesis of Functionalised 1,4-Dihydropyridines With Superb Selectivity and Yields
title_full_unstemmed A Facile and Catalyst-Free Microwave-Promoted Multicomponent Reaction for the Synthesis of Functionalised 1,4-Dihydropyridines With Superb Selectivity and Yields
title_short A Facile and Catalyst-Free Microwave-Promoted Multicomponent Reaction for the Synthesis of Functionalised 1,4-Dihydropyridines With Superb Selectivity and Yields
title_sort facile and catalyst-free microwave-promoted multicomponent reaction for the synthesis of functionalised 1,4-dihydropyridines with superb selectivity and yields
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8044462/
https://www.ncbi.nlm.nih.gov/pubmed/33869142
http://dx.doi.org/10.3389/fchem.2021.638832
work_keys_str_mv AT kerrunagaraju afacileandcatalystfreemicrowavepromotedmulticomponentreactionforthesynthesisoffunctionalised14dihydropyridineswithsuperbselectivityandyields
AT maddilasuresh afacileandcatalystfreemicrowavepromotedmulticomponentreactionforthesynthesisoffunctionalised14dihydropyridineswithsuperbselectivityandyields
AT jonnalagaddasreekanthab afacileandcatalystfreemicrowavepromotedmulticomponentreactionforthesynthesisoffunctionalised14dihydropyridineswithsuperbselectivityandyields
AT kerrunagaraju facileandcatalystfreemicrowavepromotedmulticomponentreactionforthesynthesisoffunctionalised14dihydropyridineswithsuperbselectivityandyields
AT maddilasuresh facileandcatalystfreemicrowavepromotedmulticomponentreactionforthesynthesisoffunctionalised14dihydropyridineswithsuperbselectivityandyields
AT jonnalagaddasreekanthab facileandcatalystfreemicrowavepromotedmulticomponentreactionforthesynthesisoffunctionalised14dihydropyridineswithsuperbselectivityandyields