Cyclohexanones have been converted into a variety of bicyclic azaheterocycles of different oxidation level via a sequence of reactions involving (a) imination,(b) α-alkylation with N, N- disilyl-protected ω-bromoamines,(c) transimination,(d) α-chlorination of the resulting bicyclic imines and (e) dehydrochlorination and/or dehydrogenation. Appropriate choice of the reaction conditions selectively led the reactions to indoles, 7-chloroindoles, 7- ...