NOVEL ROUTES TO INDOLES, INDOLINES, QUINOLINES AND TETRAHYDROQUINOLINES FROM N-(CYCLOHEXYLIDENE)AMINES

Cyclohexanones have been converted into a variety of bicyclic azaheter ocycles of different oxidation level via a sequence of reactions invol ving (a) imination, (b) alpha-alkylation with N,N-disilyl-protected om ega-bromoamines, (c) transimination, (d) alpha-chlorination of the res ulting bicyclic imines and (e) dehydrochlorination and/or dehydrogenat ion. Appropriate choice of the reaction conditions selectively led the reactions to indoles, 7-chloroindoles, 7-chloroindolines, 4,5,6,7-tet rahydroindoles, 8-chloro-1,2,3,4-tetrahydroquinolines, 8-chloroquinoli nes or quinolines.