A radical based addition-elimination route for the preparation of indoles

被引:28
作者
Murphy, JA
Scott, KA
Sinclair, RS
Martin, CG
Kennedy, AR
Lewis, N
机构
[1] Univ Strathclyde, Dept Pure & Appl Chem, Glasgow G1 1XL, Lanark, Scotland
[2] SmithKline Beecham Pharmaceut, Tonbridge TN11 9AN, Kent, England
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 15期
关键词
D O I
10.1039/b002565h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Indoles, including tricyclic derivatives, are produced by cyclisations of aryl radicals onto vinyl halides followed by elimination of halide radical and tautomerism of the resulting product; the aryl radicals are produced using "clean methodology" either by reaction of iodide ions with arenediazonium salts or by reaction of phosphorus-centred radicals with aryl iodides.
引用
收藏
页码:2395 / 2408
页数:14
相关论文
共 90 条
[1]   MECHANISTIC AND KINETIC-STUDIES ON THE IODODEDIAZONIATION REACTION [J].
ABEYWICKREMA, AN ;
BECKWITH, ALJ .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) :2568-2571
[2]   MECHANISTIC AND KINETIC-STUDIES OF THE THIODEDIAZONIATION REACTION [J].
ABEYWICKREMA, AN ;
BECKWITH, ALJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (26) :8227-8229
[3]   Radical cyclisation onto imidazoles and benzimidazoles [J].
Aldabbagh, F ;
Bowman, WR .
TETRAHEDRON, 1999, 55 (13) :4109-4122
[4]   CASCADE COBALT GROUP TRANSFER - RADICAL TRAPPING - TANDEM RADICAL CYCLIZATION REACTIONS IN SYNTHESIS [J].
ALI, A ;
HARROWVEN, DC ;
PATTENDEN, G .
TETRAHEDRON LETTERS, 1992, 33 (20) :2851-2854
[5]   OXIDATIVE RADICAL CYCLIZATION TO PYRROLES UNDER REDUCING CONDITIONS - REDUCTIVE DESULFONYLATION OF ALPHA-SULFONYLPYRROLES WITH TRI-N-BUTYLTIN HYDRIDE [J].
ANTONIO, Y ;
DELACRUZ, ME ;
GALEAZZI, E ;
GUZMAN, A ;
BRAY, BL ;
GREENHOUSE, R ;
KURZ, LJ ;
LUSTIG, DA ;
MADDOX, ML ;
MUCHOWSKI, JM .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (01) :15-22
[6]  
Baguley PA, 1998, ANGEW CHEM INT EDIT, V37, P3073, DOI 10.1002/(SICI)1521-3773(19981204)37:22<3072::AID-ANIE3072>3.0.CO
[7]  
2-9
[8]   3-oxa- and 3-azabicyclo[3.1.0]hexan-2-ones via tandem radical cyclization-intramolecular S(N)2 reactions [J].
Baldovini, N ;
Bertrand, MP ;
Carriere, A ;
Nouguier, R ;
Plancher, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (09) :3205-3208
[9]   HYPOPHOSPHOROUS ACID AND ITS SALTS - NEW REAGENTS FOR RADICAL CHAIN DEOXYGENATION, DEHALOGENATION AND DEAMINATION [J].
BARTON, DHR ;
JANG, DO ;
JASZBERENYI, JC .
TETRAHEDRON LETTERS, 1992, 33 (39) :5709-5712
[10]   THE INVENTION OF RADICAL REACTIONS .32. RADICAL DEOXYGENATIONS, DEHALOGENATIONS, AND DEAMINATIONS WITH DIALKYL PHOSPHITES AND HYPOPHOSPHOROUS ACID AS HYDROGEN SOURCES [J].
BARTON, DHR ;
JANG, DO ;
JASZBERENYI, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (24) :6838-6842