Tetrahedron

Novel routes to indoles, indolines, quinolines and tetrahydroquinolines from N-(Cyclohexylidene) amines

N De Kimpe, M Keppens

Index: De Kimpe, Norbert; Keppens, Marian Tetrahedron, 1996 , vol. 52, # 10 p. 3705 - 3718

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Citation Number: 43

Abstract

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- ...