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

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

doi:10.3762/bjoc.15.231

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

Beilstein J Org Chem. 2019 Oct 8:15:2390-2397. doi: 10.3762/bjoc.15.231. eCollection 2019.

Authors

Irina G Tkachenko^{1

2

3}, Sergey A Komykhov^{1

2}, Vladimir I Musatov¹, Svitlana V Shishkina^{1

2}, Viktoriya V Dyakonenko¹, Vladimir N Shvets⁴, Mikhail V Diachkov⁵, Valentyn A Chebanov^{1

2}, Sergey M Desenko^{1

2}

Affiliations

¹ State Scientific Institution "Institute for Single Crystals", National Academy of Sciences of Ukraine, Nauky Ave 60, Kharkiv 61072, Ukraine.
² Karazin Kharkiv National University, Svobody Sq. 4, Kharkiv 61022, Ukraine.
³ Kharkiv Scientific Research Forensic Center, Ministry of Internal Affairs of Ukraine, 32 Kovtuna Str., Kharkiv 61036, Ukraine.
⁴ Zaporizhzhia State Medical University, Mayakovsky Ave 26, Zaporizhzhia 69035, Ukraine.
⁵ Bar-Ilan University Ramat Gan, 5290002, Israel.

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.