Cargando…

Features of the behavior of 4-amino-5-carboxamido-1,2,3-triazole in multicomponent heterocyclizations with carbonyl compounds

Multicomponent reactions involving polyfunctional 4-amino-5-carboxamido-1,2,3-triazole and cyclic carbonyl-containing CH-acids were studied under conventional thermal heating, microwave and ultrasonic irradiation. The features of the reactions studied were discussed and the optimized procedures for...

Descripción completa

Detalles Bibliográficos
Autores principales: Gladkov, Eugene S, Gura, Katerina A, Sirko, Svetlana M, Desenko, Sergey M, Groth, Ulrich, Chebanov, Valentin A
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3520566/
https://www.ncbi.nlm.nih.gov/pubmed/23243471
http://dx.doi.org/10.3762/bjoc.8.236
_version_ 1782252798835949568
author Gladkov, Eugene S
Gura, Katerina A
Sirko, Svetlana M
Desenko, Sergey M
Groth, Ulrich
Chebanov, Valentin A
author_facet Gladkov, Eugene S
Gura, Katerina A
Sirko, Svetlana M
Desenko, Sergey M
Groth, Ulrich
Chebanov, Valentin A
author_sort Gladkov, Eugene S
collection PubMed
description Multicomponent reactions involving polyfunctional 4-amino-5-carboxamido-1,2,3-triazole and cyclic carbonyl-containing CH-acids were studied under conventional thermal heating, microwave and ultrasonic irradiation. The features of the reactions studied were discussed and the optimized procedures for the synthesis of final triazolopyrimidines were elaborated. In contrast to the similar MCRs of numerous other aminoazoles, a change of direction of the heterocyclizations in the case of 4-amino-5-carboxamido-1,2,3-triazole was not observed when microwave or thermal heating was substituted by ultrasonication at ambient temperature.
format Online
Article
Text
id pubmed-3520566
institution National Center for Biotechnology Information
language English
publishDate 2012
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-35205662012-12-14 Features of the behavior of 4-amino-5-carboxamido-1,2,3-triazole in multicomponent heterocyclizations with carbonyl compounds Gladkov, Eugene S Gura, Katerina A Sirko, Svetlana M Desenko, Sergey M Groth, Ulrich Chebanov, Valentin A Beilstein J Org Chem Full Research Paper Multicomponent reactions involving polyfunctional 4-amino-5-carboxamido-1,2,3-triazole and cyclic carbonyl-containing CH-acids were studied under conventional thermal heating, microwave and ultrasonic irradiation. The features of the reactions studied were discussed and the optimized procedures for the synthesis of final triazolopyrimidines were elaborated. In contrast to the similar MCRs of numerous other aminoazoles, a change of direction of the heterocyclizations in the case of 4-amino-5-carboxamido-1,2,3-triazole was not observed when microwave or thermal heating was substituted by ultrasonication at ambient temperature. Beilstein-Institut 2012-11-30 /pmc/articles/PMC3520566/ /pubmed/23243471 http://dx.doi.org/10.3762/bjoc.8.236 Text en Copyright © 2012, Gladkov et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Gladkov, Eugene S
Gura, Katerina A
Sirko, Svetlana M
Desenko, Sergey M
Groth, Ulrich
Chebanov, Valentin A
Features of the behavior of 4-amino-5-carboxamido-1,2,3-triazole in multicomponent heterocyclizations with carbonyl compounds
title Features of the behavior of 4-amino-5-carboxamido-1,2,3-triazole in multicomponent heterocyclizations with carbonyl compounds
title_full Features of the behavior of 4-amino-5-carboxamido-1,2,3-triazole in multicomponent heterocyclizations with carbonyl compounds
title_fullStr Features of the behavior of 4-amino-5-carboxamido-1,2,3-triazole in multicomponent heterocyclizations with carbonyl compounds
title_full_unstemmed Features of the behavior of 4-amino-5-carboxamido-1,2,3-triazole in multicomponent heterocyclizations with carbonyl compounds
title_short Features of the behavior of 4-amino-5-carboxamido-1,2,3-triazole in multicomponent heterocyclizations with carbonyl compounds
title_sort features of the behavior of 4-amino-5-carboxamido-1,2,3-triazole in multicomponent heterocyclizations with carbonyl compounds
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3520566/
https://www.ncbi.nlm.nih.gov/pubmed/23243471
http://dx.doi.org/10.3762/bjoc.8.236
work_keys_str_mv AT gladkoveugenes featuresofthebehaviorof4amino5carboxamido123triazoleinmulticomponentheterocyclizationswithcarbonylcompounds
AT gurakaterinaa featuresofthebehaviorof4amino5carboxamido123triazoleinmulticomponentheterocyclizationswithcarbonylcompounds
AT sirkosvetlanam featuresofthebehaviorof4amino5carboxamido123triazoleinmulticomponentheterocyclizationswithcarbonylcompounds
AT desenkosergeym featuresofthebehaviorof4amino5carboxamido123triazoleinmulticomponentheterocyclizationswithcarbonylcompounds
AT grothulrich featuresofthebehaviorof4amino5carboxamido123triazoleinmulticomponentheterocyclizationswithcarbonylcompounds
AT chebanovvalentina featuresofthebehaviorof4amino5carboxamido123triazoleinmulticomponentheterocyclizationswithcarbonylcompounds