Tetrahedron p. 3705 - 3718 (1996)
Update date:2022-08-04
Topics:
De Kimpe, Norbert
Keppens, Marian
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 to reactions to indoles, 7-chloroindoles, 7-chloroindolines, 4,5,6,7-tetrahydroindoles, 8-chloro-1,2,3,4-tetrahydroquinolines, 8-chloroquinolines or quinolines.
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