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

• 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

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.