Intermolecular 'oxidative' aromatic substitution reactions of the imidazol-5-yl radical mediated by the 'reductant' Bu3SnH

被引：38

作者：

McLoughlin, PTF ^{[1
]}

Clyne, MA ^{[1
]}

Aldabbagh, F ^{[1
]}

机构：

[1] Natl Univ Ireland Univ Coll Galway, Dept Chem, Galway, Ireland

来源：

TETRAHEDRON | 2004年 / 60卷 / 37期

关键词：

free radicals; heterocycles; imidazoles; tributyltin hydride;

D O I：

10.1016/j.tet.2004.06.120

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactivity of the imidazol-5-yl in comparison to the imidazol-2-yl and phenyl radical under the reductive conditions of Bu3SnH, in intermolecular substitution reactions onto various aromatic substrates is reported. The directing effect of the hetero atom or methyl substituent in aromatic substrates was found to be more important than the polarity of the attacking sigma-radical in determining the major product isomer. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：8065 / 8071

页数：7

共 30 条

[1] Bu3SnH mediated oxidative radical cyclisation onto imidazoles and pyrroles [J].

Aldabbagh, F ;

Bowman, WR ;

Mann, E ;

Slawin, AMZ .

TETRAHEDRON, 1999, 55 (26) :8111-8128

[2] The mechanism of Bu3SnH-mediated homolytic aromatic substitution [J].

Beckwith, ALJ ;

Bowry, VW ;

Bowman, WR ;

Mann, E ;

Parr, J ;

Storey, JMD .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (01) :95-98

[3] Preparation of β- and γ-lactams via ring closures of unsaturated carbamoyl radicals derived from 1-carbamoyl-1-methylcyclohexa-2,5-dienes [J].

Bella, AF ;

Jackson, LV ;

Walton, JC .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (03) :421-428

[4] New cascade 2-indolylacyl radical addition-cyclization reactions [J].

Bennasar, ML ;

Roca, T ;

Griera, R ;

Bosch, J .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (22) :7547-7551

[5] Synthesis of heterocycles by radical cyclisation [J].

Bowman, WR ;

Fletcher, AJ ;

Potts, GBS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (24) :2747-2762

[6] IMIDAZOL-5-YL RADICALS AS REACTIVE INTERMEDIATES [J].

BOWMAN, WR ;

TAYLOR, PF .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (04) :919-924

[7] OXIDATION DURING REDUCTIVE CYCLIZATIONS USING BU3SNH [J].

BOWMAN, WR ;

HEANEY, H ;

JORDAN, BM .

TETRAHEDRON, 1991, 47 (48) :10119-10128

[8]

COMINS DL, 1990, HETEROCYCLES, V31, P2025

[9] Synthesis of carbazomycin B by radical arylation of benzene [J].

Crich, D ;

Rumthao, S .

TETRAHEDRON, 2004, 60 (07) :1513-1516

[10] AMIDE-BASED PROTECTING/RADICAL TRANSLOCATING (PRT) GROUPS - GENERATION OF RADICALS ADJACENT TO CARBONYLS BY 1,5-HYDROGEN TRANSFER-REACTIONS OF O-IODOANILIDES [J].

CURRAN, DP ;

YU, HS ;

LIU, HT .

TETRAHEDRON, 1994, 50 (25) :7343-7366

← 1 2 3 →