The synthesis of 9-azasteroids—II: Synthesis of β-cyano- and β-carbethoxy-3- and 4-oxo-1,2,3,4,5,6-hexahydrobenzo[c]quinolizines☆

Add time:08/12/2019    Source:sciencedirect.com

The synthesis of 3-cyano-4-oxo-1,2,3,4,5,6-hexahydrobenzo[c]quinolizine (XIV), of 2-carbethoxy-3-oxo-1,2,3,4,5,6-hexahydrobenzo[c]quinolizine(XVII), and of 4-cyano-3-oxo-1,2,3,4,5,6-hexahydrobenzo[c]quinolizine (XXIX) is reported. Attempts to methylate 3-carbethoxy-4-oxo-1,2,3,4,5,6-hexahydrobenzo[c]quinolizine (II) were unsuccessful, although the keto-ester (II) was nitrated successfully to give the nitro compound (X). Similar nitration of the di-ester (VIII) gave the nitro diester (IX). Methylation of the keto-ester (XVII) with subsequent decarboxylation gave the methyl ketone (XXI). The isomeric ketone (XX) has been synthesized.

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