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. 2019 Oct 8:15:2390-2397.
doi: 10.3762/bjoc.15.231. eCollection 2019.

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

Irina G Tkachenko  1   2   3 , Sergey A Komykhov  1   2 , Vladimir I Musatov  1 , Svitlana V Shishkina  1   2 , Viktoriya V Dyakonenko  1 , Vladimir N Shvets  4 , Mikhail V Diachkov  5 , Valentyn A Chebanov  1   2 , Sergey M Desenko  1   2
Affiliations

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

Irina G Tkachenko et al. Beilstein J Org Chem. .

Abstract

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.

Keywords: 1,3-dicarbonyl compounds; 5-aminotetrazole; antioxidant activity; multicomponent synthesis; tetrazolo[1,5-a]pyrimidines.

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Figures

Scheme 1
Scheme 1
Three synthetic approaches to dihydrotetrazolo[1,5-a]pyrimidines.
Scheme 2
Scheme 2
Three-component reaction of 1, 7a,b and 8a–d in water.
Figure 1
Figure 1
Molecular structure of 9a according to X-ray data. Displacement ellipsoids are shown at the 50% probability level.
Scheme 3
Scheme 3
Three-component reaction of 5-aminotetrazole (1) with formaldehyde (7a) and acetylacetone (10).
Scheme 4
Scheme 4
a) Three-component reaction of 5-aminotetrazole (1) with acetaldehyde (7b) and ethyl 4,4,4-trifluoroacetoacetate (13); b) structure investigation of 14 by NMR.
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