New spiro derivative of dihydro-1,2,3-triazolo[1,5-a]pyrimidine as a product of multicomponent reaction.

Gladkov, Eugene S.; Sirko, Svetlana M.; Musatov, Vladimir I.; Shishkina, Svetlana V.; Tkachenko, Irina G.; Komykhov, Sergey A.; Desenko, Sergey M.

A new spiro derivative of dihydro-1,2,3-triazolo[1,5-a]pyrimidine - 5'-amino-6'-cyano-4'H-spiro[cyclohexane-1,7'-[1,2,3]triazolo[1,5-a]-pyrimidine]-3'-carboxamide - was prepared by three-component reaction of 5-amino-1,2,3-triazole-4-carboxamide with malononitrile and cyclohexanone; the structure of product was established by X-ray analysis. Microwave activation and conventional heating showed the formation of single product and the same direction of heterocyclization. Available literature data concerning similar reactions using 3-amino-1,2,4-triazole or 2-aminobenzimidazole were reinvestigated experimentally with consideration of alternative structures; structures of products were studied by NMR including NOE experiments.

PYRIMIDINES; CHEMICAL reactions; CHEMICAL derivatives; CARBOXAMIDES; MALONONITRILE; CYCLOHEXANONES

Chemistry of Heterocyclic Compounds, 2018, Vol 54, Issue 12, p1139

0009-3122

Academic Journal

10.1007/s10593-019-02405-9