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

被引：37

作者：

DeKimpe, N

Keppens, M

机构：

[1] Department of Organic Chemistry, Fac. of Agric. and Appl. Biol. Sci., University of Gent, B-9000 Gent

来源：

TETRAHEDRON | 1996年 / 52卷 / 10期

关键词：

D O I：

10.1016/0040-4020(96)00046-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclohexanones have been converted into a variety of bicyclic azaheterocycles of different oxidation level via a sequence of reactions involving (a) imination, (b) alpha-alkylation with N,N-disilyl-protected omega-bromoamines, (c) transimination, (d) alpha-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-chloroindolines, 4,5,6,7-tetrahydroindoles, 8-chloro-1,2,3,4-tetrahydroquinolines, 8-chloroquinolines or quinolines.

引用

页码：3705 / 3718

页数：14

共 22 条

[1]

AMBEKAR SY, 1964, J KARNATAK U, V9, P5

[2] TRANSANNULAR REACTIONS OF PEPTIDES - THE PEPTIDE NITROGEN IN A 10-MEMBERED RING [J].