A tandem radical addition/cyclization process of 1-(2-iodoethyl)indoles and methyl acrylate

被引:37
作者
Miranda, LD
Cruz-Almanza, R
Pavón, M
Romero, Y
Muchowski, JM
机构
[1] Univ Nacl Autonoma Mexico, Inst Quim, Mexico City 04510, DF, Mexico
[2] Univ Autonoma Estado Mexico, Fac Quim, Mexico City 05000, DF, Mexico
[3] Roche Biosci, Palo Alto, CA 94304 USA
关键词
radical cycloaddition; radical addition; hexabutylditin; indole systems;
D O I
10.1016/S0040-4039(00)01829-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Benzindolizidine systems are generated in moderate yields by a hexabutylditin mediated consecutive radical addition, cyclization, oxidation process from 1-(2-iodoethyl)indoles and methyl acrylate. (C) 2000 Published by Elsevier Science Ltd.
引用
收藏
页码:10181 / 10184
页数:4
相关论文
共 16 条
[1]   OXIDATIVE RADICAL CYCLIZATION OF (OMEGA-IODOALKYL)INDOLES AND PYRROLES - SYNTHESIS OF (-)-MONOMORINE AND 3 DIASTEREOMERS [J].
ARTIS, DR ;
CHO, IS ;
JAIMEFIGUEROA, S ;
MUCHOWSKI, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) :2456-2466
[2]   Bu3SnH mediated oxidative radical cyclisations:: synthesis of 6H-benzo[c]chromen-6-ones [J].
Bowman, WR ;
Mann, E ;
Parr, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (17) :2991-2999
[3]   EFFECTS OF TEMPERATURE ON ATOM TRANSFER CYCLIZATION REACTIONS OF ALLYLIC ALPHA-IODO ESTERS AND AMIDES [J].
CURRAN, DP ;
TAMINE, J .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2746-2750
[4]   ATOM TRANSFER CYCLIZATION OF SIMPLE HEXENYL IODIDES - A CAUTION ON THE USE OF ALKENYL IODIDES AS PROBES FOR THE DETECTION OF SINGLE ELECTRON-TRANSFER PROCESSES [J].
CURRAN, DP ;
KIM, D .
TETRAHEDRON LETTERS, 1986, 27 (48) :5821-5824
[5]   THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .1. [J].
CURRAN, DP .
SYNTHESIS-STUTTGART, 1988, (06) :417-439
[6]   ATOM TRANSFER CYCLOADDITION - A FACILE PREPARATION OF FUNCTIONALIZED (METHYLENE)CYCLOPENTANES [J].
CURRAN, DP ;
CHEN, MH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (21) :6558-6560
[7]  
Giese B., 1986, RADICALS ORGANIC SYN
[8]  
Kaoudi T, 2000, ANGEW CHEM INT EDIT, V39, P731, DOI 10.1002/(SICI)1521-3773(20000218)39:4<731::AID-ANIE731>3.3.CO
[9]  
2-L
[10]   A NEW-ONE-ELECTRON-CARBON-CARBON BOND FORMING REACTION - SEPARATION OF THE CHAIN PROPAGATION STEPS IN FREE-RADICAL ALLYLATION [J].
KECK, GE ;
BYERS, JH .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) :5442-5444