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NEW SPIRO DERIVATIVE OF DIHYDRO-1,2,3-TRIAZOLO[1,5-a]PYRIMIDINE AS A PRODUCT OF MULTICOMPONENT REACTION

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


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.

Keywords


1,2,3-triazole derivatives; microwave synthesis; molecular structure investigation; multicomponent reactions; reaction mechanism; X-ray analysis

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