Reactions of Guanidine and Urea with Aminonitriles

Article abstract of DOI:10.1007/BF00905077

The aminonitriles 3a-f react with guanidine in DMF to yield the 5,5- resp. 5-substituted imidazolidine-2,4-diimines 2a-d resp. 2f, whereas 2e could not be isolated. 7,14-diazadispiro<5.1.5.2>-pentadecan-15-on (7), 4-imino-1,3-diazaspiro<4.5>decan-2-one (8a) and the 2,4-diaminotriazine (9) were isolated as byproducts. 1-Aminocyclohexancarbonitrile (3a) reacts with urea to the 4-imino-1,3-diazaspiro<4.5>decan-2-one (8a); 8a can be prepared from (1-cyancyclohexyl)urea (11a) as well.The structures of the new compounds are proved by NMR-, IR- and mass spectra and the mechanism of the reaction is discussed. - Keywords: Aminonitriles, reaction with guanidine resp. urea; 1,3-Diazaspiro<4.5>decan-2-one, 4-imino; 1,3-Diazaspiro<4.4>nonan-resp. <4.5>decan-2,4-diimimne; Guanidine, reactions with aminonitriles; Imidazolidin-2,4-diimines, 5-substituted; Urea, reactions with aminonitriles