Abstract
Action of guanidine or urea on cyclohexanone-, cyclopentanone-, cycloheptanone-and acetonecyanohydrine3 a−3 d generates very different products:
3 a reacts with guanidine inDMF to yield 1,3-diazaspiro[4.5]decane-2,4-diimine (5 a). Heating the components without solvent affords 7,14-diazadispiro[5.1.5.2]pentadecan-15-one(7)15–17, the guanidine not participating in the reaction; similarly3 b is transformed by guanidine to a pentacyclic dispirocompound (possible formulae19 and20), whereas3 d reacts to give 3,3,5,5-tetramethylpiperazine-2,6-dione(21)19. In 3-pentanone guanidine-cyanide condensates itself to give 2,4-diamino-triazine (22)21, 22.
Action of urea on3 a−3 d yields the 4-imino-1,3-diazaspiroalkan-2-ones6 a−6 c and the 4-imino-5,5-dimethylimidazolidin-2-one6 d 6–8 resp. If the reaction of urea and3 d is carried out inDMF, however, 5,5-dimethyl-4-ureido-3-imidazolin-2-one (28) (or the tautomeric carbamoyliminoimidazolidinone27) is produced.
The structures of the compounds prepared are proved by NMR-, IR- and mass spectra.
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Herrn Prof. Dr.G. Zigeuner zum 60. Geburtstag gewidmet.
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Wendelin, W., Schramm, HW. & Zmölnig, I. Über die Reaktionen von Guanidin bzw. Harnstoff mit Cyanhydrinen. Monatshefte für Chemie 112, 853–866 (1981). https://doi.org/10.1007/BF00899786
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DOI: https://doi.org/10.1007/BF00899786