Studies on Quinolizine Derivatives. XXIII. : Synthesis and Reactions of Methylthioazacycl[3.3.3]azines

Abstract

Dimethyl 7-acyl-9-cyano-1-azacycl[3.3.3]azine-2, 3-dicarboxylates (4, 6) were synthesized via 1-acyl-3-cyano-4-imino-4H-quinolizines (3, 5) as key intermediates. The nucleophilic substitution of the methylthio group in antiaromatic azacycl[3.3.3]azines (6b, 9, 13) gave the corresponging producs. The reaction of 9 or 13 with methyl acetoacetate gave the fused diazacycl[3.3.3]azines (12, 16), which are examples of a new ring system.