Application of a radical catalysed isomerisation reaction to the synthesis of fused [1,2-a]indoles

被引：11

作者：

Caddick, S ^{[1
]}

Shering, CL ^{[1
]}

Wadman, SN ^{[1
]}

机构：

[1] GLAXO WELLCOME RES & DEV LTD,MED RES CTR,STEVENAGE SG1 2NY,HERTS,ENGLAND

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 35期

基金：

英国工程与自然科学研究理事会; 英国生物技术与生命科学研究理事会;

关键词：

D O I：

10.1016/S0040-4039(97)01378-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new radical triggered isomerisation approach to fused indoles is presented; the proposed mechanism involves the radical cyclization of a beta-toluenesulfonyl-vinyl radical or beta-toluenesulfonyl-alkyl radical onto a sulfone substituted indole and is catalysed with Se-phenyl-p-toluene-selenosulfonate (TsSePh). (C) 1997 Elsevier Science Ltd.

引用

页码：6249 / 6250

页数：2

共 18 条

[1] Preparation of organostannanes by intermolecular radical substitution reactions [J].

Aboutayab, K ;

Caddick, S ;

Jenkins, K ;

Joshi, S ;

Khan, S .

TETRAHEDRON, 1996, 52 (34) :11329-11340

[2] A CONVENIENT SYNTHESIS OF SELENOLSULFONATES FROM THE OXIDATION OF SULFONHYDRAZIDES WITH BENZENESELENINIC ACID [J].

BACK, TG ;

COLLINS, S .

TETRAHEDRON LETTERS, 1980, 21 (23) :2213-2214

[3] RECENT PROGRESS IN THE USE OF SULFONYL RADICALS IN ORGANIC-SYNTHESIS - A REVIEW [J].

BERTRAND, MP .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1994, 26 (03) :257-290

[4]

BHAWGWAT SS, 1994, TETRAHEDRON LETT, V35, P1847

[5]

CADDICK S, 1993, SYNLETT, P231

[6] Intramolecular radical substitution reactions: A novel approach to fused [1,2-a]indoles [J].

Caddick, S ;

Aboutayab, K ;

Jenkins, K ;

West, RI .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (07) :675-682

[7]

CADDICK S, 1997, J CHEM SOC CHEM COMM, P171

[8]

Chatgilialoglu C., 1988, CHEM SULFONES SULFOX, P1089

[9]

CURRAN DP, 1991, CHEM REV, V91, P1237

[10]

GUNG J, 1997, TETRAHEDRON LETT, V38, P787

← 1 2 →