ISSN:
1434-4475
Keywords:
Guanidine, reactions with ketones
;
Ketones, reactions with guanidine
;
2,4-Pyrimidindiamine, 6-phenyl
;
Spiro [cyclopentan-1,4′-cyclopentapyrimidin]-2′ (3′ H)-imine, 1′,5′,6′,7′-tetrahydro
;
1,3,5-Triazaspiro[5.5]undeca-and [5.6]dodeca-1,3-dien-2,4-diamine
;
1,3,5-Triazine-2,4-diamines, 1,6-dihydro-6,6-dialkyl, and salts
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00909677
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