THE CHEMISTRY OF THE PYRIDO[4,3-B]CARBAZOLES .15. THE SYNTHESIS OF UNSYMMETRICALLY 1,4-DISUBSTITUTED CARBAZOLES AND THEIR USE IN THE SYNTHESIS OF 6H-PYRIDO[4,3-B]CARBAZOLES

被引：32

作者：

HOGAN, I ^{[1
]}

JENKINS, PD ^{[1
]}

SAINSBURY, M ^{[1
]}

机构：

[1] UNIV BATH,SCH CHEM,CLAVERTON DOWN,BATH BA2 7AY,AVON,ENGLAND

来源：

TETRAHEDRON | 1990年 / 46卷 / 08期

关键词：

D O I：

10.1016/S0040-4020(01)88387-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new construction of unsymmetrically 1,4-disubsitued carbazoles has been devised and used in the synthesis of the alkaloid olivacine. The starting materials are gramines and the sodium salts of 2-cyano-4-oxopentanonitriles. These afford 4-cyano-5-(indol-3-yl)pentan-2-ones, which can be cyclised by treatment with acetic acid and then aromatised to yield carbazoles suitably functionalised for subsequent conversion into 6H-pyrido[4,3-b]carbazoles unsymmetrically substituted at C-5 and C-ll. Attempts to develop this as a general approach to 5-alkylamino-6H]-pyrido[4,3b]carbazoles have, However, encountered a number of unforeseen problems. © 1990.

引用

页码：2943 / 2964

页数：22

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