Abstract
Various 5,9b-dihydrobenz[e]indolines were synthesized by three general methods: (a) by alkylation with the appropriate alkyl halide of 1,2,4,5-tetrahydro-1H-benz[e]indoles, themselves obtained by alkylation with bromochloroethane of enamines derived from 7-alkoxy-2- tetralones; (b) from 1-alkylaminoethyl-2,2-ethylenedioxy-1,2,3,4-tetrahydronaphthalenes by acid hydrolysis, and (c) by reduction of 2-oxo-2,3,5,9b-tetrahydro-1 H-benz[e]indoles which in turn were obtained from ethyl 2-oxo-1,2,3,4-tetrahydro-1-naphthalene acetates by reaction with methylamine followed by dehydration. These substances are key intermediates in the synthesis of 9-oxobenzomorphans.
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