Synthesis of 2,3,4,4a,9,9a-hexahydro-3,9-methano-1H-indeno[2,1-c]pyridine and some N-substituted derivatives

Abstract

The construction of the very rigid 2,3,4,4a,9,9a-hexahydro-3,9-methano-1H-indeno[2,1-c]pyridine system by three different routes is presented. One of the routes led also to another novel azabenzotricyclodecane system, viz. to the compound 2-(p-tolylsulphonyl)-1,2,3,3a,8,8a-hexahydro-3,8-ethanoindeno[1,2-c]pyrrole, which was the result of a skeletal rearrangement. The last of the routes gives easy access to the title compound and its derivatives.