W. Wendelin, I. Zmölnig, H. Schramm
Sep 1, 1980
Citations
0
Influential Citations
3
Citations
Journal
Monatshefte für Chemie / Chemical Monthly
Abstract
Guanidine reacts with cyclohexanone, cycloheptanone, acetone and 3-pentanone, resp., in a molar ratio 2∶1 to give the 1,3,5-triazaspiro[5.5]undeca-and [5.6]dodeca-1,3-dien-2,4-diamines3 a and3 b resp. and the 6,6-dimethylresp. diethyl-1,6-dihydro-1,3,5-triazin-2,4-diamines3 d and3 e resp. On the contrary, action of guanidine on cyclopentanone yields not3 c, but the 1′,5′,7′-tetrahydrospiro[cyclopentane-1,4′-cyclopentapyrimidine]-2′(3′H)-imines2 c, 5 c and6 c resp., which are 1∶2- and 1∶3-condensates. Phenylacetone is transformed by guanidine (1∶2) to give 6-phenyl-2,4-pyrimidindiamine (8 f).The structure of the compounds cited is proved by NMR-, IR-, and (partially) mass spectra. The different courses of the formation of3 a, b, d, e, 2 c, 5 c and6 c resp. and8 f are also discussed.The structural formulae of some additional bases, which were synthesized from guanidine and cyclopentanone, 3-pentanone and phenylacetone resp. could not be established.