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Reaction of 3, 4-dihydroisoquinolineacetonitrile (I) and methyl 1-cyano-2, 2-dimethylthioacrylate (II) gave 3-cyano-2-methylthio-4-oxo-6, 7-dihydrobenzo [α] quinolizines (III). III reacted with various amines to form 1, 3-dicyano-2-amino-4-oxo-6, 7-dihydrobenzo-[α] quinolizines (IVa-g). III also reacted with active methylene compounds to form 1, 3-dicyano-4-oxo-6, 7-dihydrobenzo [α] quinolizines (V-IX).In the reaction of 1, 3-dicyano-2-methylthio-4-oxo-6, 7-dihydrobenzo [α] quinolizines (IIIna) and 2-amino-1, 3-dicyano-4-oxo-6, 7-dihydrobenzo [α] quinolizine (IVd) with concentrated sulfuric acid, the cyano group in 1-position was found to be easily liberated and that in 3-position was converted into a carboxamide group.Reduction of 1, 3-dicyano-4-oxo-6, 7-dihydrobenzo [α] quinolizines (IIIa, b, IVa, Vb) with sodium borohydride in ethanol or N, N-dimethylformamide gave 1, 3-dicyano-4-oxo-1, 6, 7, 11b-tetrahydro-9, 10-dimetoxybenzo [α] quinolizines (XI, XIIa, b, XIII) by the reduction of quinolizine skeleton.

Studies of Quinolizine Derivatives. V. Synthesis of 3-Cyano-2-methylthio-4-oxo-6, 7-dihydrobenzo [α] quinolizines and Their Reactions