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

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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Bibliographic Details
Main Authors: Irina G. Tkachenko, Sergey A. Komykhov, Vladimir I. Musatov, Svitlana V. Shishkina, Viktoriya V. Dyakonenko, Vladimir N. Shvets, Mikhail V. Diachkov, Valentyn A. Chebanov, Sergey M. Desenko
Format: Article
Language:English
Published: Beilstein-Institut 2019-10-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
5-aminotetrazole
antioxidant activity
1,3-dicarbonyl compounds
multicomponent synthesis
tetrazolo[1,5-a]pyrimidines
Online Access:https://doi.org/10.3762/bjoc.15.231
Description
Summary: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.
ISSN:1860-5397

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