Regioselective Synthesis and Stereochemical Structure of 1,2,8,9,13-Pentaazadispiro[4.1.4.3]Tetradeca-2,9-Dien-6-Ones

Abstract

A facile regioselective synthetic approach towards 1,3,4,8,10,11-hexaaryl-13-methyl-1,2,8,9,13-pentaazadispiro [4.1.4.3]tetradeca-2,9-dien-6-ones 3a–g was achieved through the reaction of 3,5-bis(arylmethylene)-1-methyl-4-piperidinones 1a–f with nitrilimines (generated in situ by triethylamine dehydrohalogenation of the corresponding hydrazonoyl chlorides 2a,b). The stereochemical configuration of the isolated products was established to be 4 S, 5 R, 7 R, 11 S based on a single crystal X-ray diffraction study of 3b.