Polycyclic N-Hetero Compounds. VII. Reactions of Benzyl Ketones with Formamide XI

On heating phenylacetone (III) with formamide in the presence of phosphoryl chloride (called the modified Vilsmeier reaction) afforded 4-methyl-5-phenylpyrimidine (IV), 5-phenyl-4-(5-pyrimidinyl) pyrimidine (V), and 3-methyl-2, 4-diphenylaniline (VI). The modified Vilsmeier reaction of 3-methoxyphenylacetone (VII) gave 6-methoxy-3-methylisoquinoline (VIII), 4-β-formylaminovinyl-5-m-methoxyphenylpyrimidine (IX), 9-methoxybenzo [f] quinazoline (X), and 7-methoxybenzo [f] quinazoline (XI). The same reaction of 2-phenylcyclohexanone (XII) gave 8-phenyl-5, 6, 7, 8-tetrahydroquinazoline (XIII) and 4-formylamino-4, 4a, 5, 6, 7, 8-hexahydroquinazoline (XIV).