In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines

The three-component reaction of 5-aminotetrazole with aliphatic aldehydes (formaldehyde, acetaldehyde) and acetoacetic ester derivatives in water under microwave irradiation leads to the selective formation of 4,7-dihydrotetrazolo[1,5-a]pyrimidine derivatives. Under similar conditions using 4,4,4-tr...

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Autores principales: Tkachenko, Irina G, Komykhov, Sergey A, Musatov, Vladimir I, Shishkina, Svitlana V, Dyakonenko, Viktoriya V, Shvets, Vladimir N, Diachkov, Mikhail V, Chebanov, Valentyn A, Desenko, Sergey M
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2019
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6808202/
https://www.ncbi.nlm.nih.gov/pubmed/31666873
http://dx.doi.org/10.3762/bjoc.15.231
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author Tkachenko, Irina G
Komykhov, Sergey A
Musatov, Vladimir I
Shishkina, Svitlana V
Dyakonenko, Viktoriya V
Shvets, Vladimir N
Diachkov, Mikhail V
Chebanov, Valentyn A
Desenko, Sergey M
author_facet Tkachenko, Irina G
Komykhov, Sergey A
Musatov, Vladimir I
Shishkina, Svitlana V
Dyakonenko, Viktoriya V
Shvets, Vladimir N
Diachkov, Mikhail V
Chebanov, Valentyn A
Desenko, Sergey M
author_sort Tkachenko, Irina G
collection PubMed
description The three-component reaction of 5-aminotetrazole with aliphatic aldehydes (formaldehyde, acetaldehyde) and acetoacetic ester derivatives in water under microwave irradiation leads to the selective formation of 4,7-dihydrotetrazolo[1,5-a]pyrimidine derivatives. Under similar conditions using 4,4,4-trifluoroacetoacetic ester 5-hydroxy-4,5,6,7-tetrahydrotetrazolo[1,5-a]pyrimidines are obtained. The analogous reaction with acetylacetone requires scandium(III) triflate as catalyst. The antioxidant activity of selected compounds was assayed with 1,1-diphenyl-2-picrylhydrazyl.
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spelling pubmed-68082022019-10-30 In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines Tkachenko, Irina G Komykhov, Sergey A Musatov, Vladimir I Shishkina, Svitlana V Dyakonenko, Viktoriya V Shvets, Vladimir N Diachkov, Mikhail V Chebanov, Valentyn A Desenko, Sergey M Beilstein J Org Chem Full Research Paper The three-component reaction of 5-aminotetrazole with aliphatic aldehydes (formaldehyde, acetaldehyde) and acetoacetic ester derivatives in water under microwave irradiation leads to the selective formation of 4,7-dihydrotetrazolo[1,5-a]pyrimidine derivatives. Under similar conditions using 4,4,4-trifluoroacetoacetic ester 5-hydroxy-4,5,6,7-tetrahydrotetrazolo[1,5-a]pyrimidines are obtained. The analogous reaction with acetylacetone requires scandium(III) triflate as catalyst. The antioxidant activity of selected compounds was assayed with 1,1-diphenyl-2-picrylhydrazyl. Beilstein-Institut 2019-10-08 /pmc/articles/PMC6808202/ /pubmed/31666873 http://dx.doi.org/10.3762/bjoc.15.231 Text en Copyright © 2019, Tkachenko et al. https://creativecommons.org/licenses/by/4.0https://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/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. 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
Tkachenko, Irina G
Komykhov, Sergey A
Musatov, Vladimir I
Shishkina, Svitlana V
Dyakonenko, Viktoriya V
Shvets, Vladimir N
Diachkov, Mikhail V
Chebanov, Valentyn A
Desenko, Sergey M
In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines
title In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines
title_full In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines
title_fullStr In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines
title_full_unstemmed In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines
title_short In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines
title_sort in water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6808202/
https://www.ncbi.nlm.nih.gov/pubmed/31666873
http://dx.doi.org/10.3762/bjoc.15.231
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