Ultrasonic-assisted unusual four-component synthesis of 7-azolylamino-4,5,6,7-tetrahydroazolo[1,5- a]pyrimidines

Yana I Sakhno; Maryna V Murlykina; Oleksandr I Zbruyev; Anton V Kozyryev; Svetlana V Shishkina; Dmytro Sysoiev; Vladimir I Musatov; Sergey M Desenko; Valentyn A Chebanov

doi:10.3762/bjoc.16.27

Ultrasonic-assisted unusual four-component synthesis of 7-azolylamino-4,5,6,7-tetrahydroazolo[1,5- a]pyrimidines

Beilstein J Org Chem. 2020 Feb 27:16:281-289. doi: 10.3762/bjoc.16.27. eCollection 2020.

Authors

Affiliations

¹ Division of Chemistry of Functional Materials, State Scientific Institution "Institute for Single Crystals" of National Academy of Sciences of Ukraine, Nauky Av. 60, 61072 Kharkiv, Ukraine.
² Faculty of Chemistry, V. N. Karazin Kharkiv National University, Svobody Sq. 4, 61077 Kharkiv, Ukraine.
³ Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo náměstí 542/2, 166 10 Praha 6, Czech Republic.

Abstract

Four-component reactions of 3-amino-1,2,4-triazole or 5-amino-1H-pyrazole-4-carbonitrile with aromatic aldehydes and pyruvic acid or its esters under ultrasonication were studied. Unusual for such a reaction type, a cascade of elementary stages led to the formation of 7-azolylaminotetrahydroazolo[1,5-a]pyrimidines.

Keywords: 3-amino-1,2,4-triazole; 5-amino-1H-pyrazole-4-carbonitrile; 7-azolylaminotetrahydroazolo[1,5-a]pyrimidines; heterocycle; multicomponent reaction; ultrasonication.

Grants and funding

The authors thank the National Academy of Sciences of Ukraine for financial support in the frame of the projects "Creation of modern bases for obtaining and analyzing substances and components of materials for pharmaceutical purposes" (0119U100727) and "Investigation of structural features of nitrogen containing heterocycles with potential biological activity" (0119U100716). M. Murlykina was supported by the Grant of National Academy of Sciences of Ukraine for young scientists’ research laboratories and groups (0118U100275).