Free radical reactions for heterocycle synthesis.: Part 4:: A double ipso substitution reaction for azacoumarins

被引:39
作者
Zhang, W [1 ]
Pugh, G [1 ]
机构
[1] Dupont Co Inc, Stine Haskell Res Ctr, Crop Protect, Lead Discovery, Newark, DE 19714 USA
关键词
D O I
10.1016/S0040-4039(01)01089-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly efficient route to azacoumarins with an unusual mechanism of double ipso substitutions is described. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5613 / 5615
页数:3
相关论文
共 30 条
[1]   Novel intramolecular rearrangement of 3-bromo-3,3-difluoroalanine Schiff bases via radical ipso-substitution at the aromatic ring [J].
Amii, H ;
Kondo, S ;
Uneyama, K .
CHEMICAL COMMUNICATIONS, 1998, (17) :1845-1846
[2]   INTRA-MOLECULAR HOMOLYTIC AROMATIC IPSO SUBSTITUTION IN HALOGENOBENZENES BY ARYL RADICALS [J].
BENATI, L ;
MONTEVECCHI, PC ;
TUNDO, A .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (13) :530-531
[3]   A SHORT SYNTHESIS OF DIBENZOFURANS AND DIBENZOTHIOPHENES [J].
BLACK, M ;
CADOGAN, JIG ;
MCNAB, H .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (05) :395-396
[4]  
Bonfand E, 1997, HETEROCYCLES, V46, P523
[5]  
Bonfand E, 2000, SYNLETT, P475
[6]   NOVEL INTRAMOLECULAR RADICAL DISPLACEMENT-REACTIONS OF 2-INDOLYL ARYL SULFIDES AND SULFOXIDES [J].
CADDICK, S ;
ABOUTAYAB, K ;
WEST, RI .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (13) :1353-1354
[7]   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
[8]  
Crooke D FB, 1997, Coumarins: Biology, Applications and Mode of Action, P303
[9]   Observations on the nature of the tethering chain in the synthesis of biaryls and heterobiaryls via intramolecular free radical ipso substitution reactions. [J].
daMata, MLEN ;
Motherwell, WB ;
Ujjainwalla, F .
TETRAHEDRON LETTERS, 1997, 38 (01) :141-144
[10]   Steric and electronic effects in the synthesis of biaryls and their heterocyclic congeners using intramolecular free radical [1,5] ipso substitution reactions. [J].
daMata, MLEN ;
Motherwell, WB ;
Ujjainwalla, F .
TETRAHEDRON LETTERS, 1997, 38 (01) :137-140