Studies on Quinolizine Derivatives. XIV. Synthesis of Azacycl[3, 3, 3]azine Derivatives. (7)

Abstract

4-Imino-6-methyl-4H-quinolizine derivatives (XIII) were easily obtained by the reaction of 6-methyl-2-pyridineacetate derivatives (XI) with ethoxymethylenemalononitrile (XII). The reaction of XI with ethyl ethoxymethylenecyanoacetate (XIV) afforded ethyl 4-substituted-2-cyano-4-(6-methyl-2-pyridyl)-crotonate derivatives (XV). New nitrogen-bridged [12]annulene heterocyclic systems, 1-azacycl[3, 3, 3]azine derivatives (XVII, XVIII) were obtained by the reaction of XIII or XV with XII or acetic anhydride.