Polycyclic N-Hetero Compounds. VIII. Reactions of Ketones with Trisformylaminomethane

Reactions of ketones with trisformylaminomethane were described. Except pyrimidine derivatives reported by Bredereck, et al., few by-products were obtained. Thus methyl ethyl ketone (I) gave 4-ethylpyrimidine (III) and 5-methyl-4-(5-pyrimidinyl) pyrimidine (IV), diethyl ketone (V) gave 4-amino-3, 5-dimethylpyridine (VII), cyclohexanone (VIII) gave bis (5, 6, 7, 8-tetrahydro-8-quinazolinylidenemethyl) amine (X). 4-Methyl-5-phenylpyrimidine (XII) and 8-phenyl-5, 6, 7, 8-tetrahydroquinazoline (XIV) were obtained from phenylacetone (XI) and 2-phenylcyclohexanone (XIII) respectively. Dehydrogenation of (XIV) with sulfur afforded 8-phenylquinazoline (XV).