A. O. Kurskova, V. Dotsenko, K. Frolov
Jun 1, 2021
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Journal
Russian Journal of General Chemistry
Abstract
Sequential reaction of cyclohexanone with malononitrile and 2-aminopropene-1,1,3-tricarbonitrile in the presence of potassium hydroxide or sodium ethylate in ethanol gave 4-imino-2-(dicyanomethylene)-3-azaspiro[5.5]undecane-1,5-dicarbonitrile. The latter reacted with primary amines and an excess of formaldehyde to form new 2-(dicyanomethylene)-3,7-diazaspiro[bicyclo[3.3.1]non-3-ene-9,1′-cyclohexane]-1.5-dicarbonitrile derivatives. Contrary to the literature data, the reaction of cyclohexanone with 2-aminopropene-1,1,3-tricarbonitrile in benzene in the presence of piperidine and glacial acetic acid led to the formation of 2,4-diamino-5,6,7,8-tetrahydronaphthalene-1,3-dicarbonitrile.