Captodative olefins: methyl 2-aryloxy-3-dimethylaminopropenoates and their application in a new synthesis of benzofurans

被引:37
作者
Cruz, MD [1 ]
Tamariz, J [1 ]
机构
[1] Escuela Nacl Ciencias Biol, Dept Quim Organ, Inst Politecn Nacl, Mexico City 11340, DF, Mexico
关键词
captodative olefins; 2-aryloxy-3-dimethylaminopropenoates; benzofurans; cyclization; Lewis acid catalysis;
D O I
10.1016/j.tetlet.2004.01.073
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The beta-substituted captodative olefins methyl 2-aryloxy-3-dimethylaminopropenoates 4a-h were synthesized, via amino-methylenation of the corresponding 2-phenoxyacetic esters 9a-h. Lewis acid promoted intramolecular cyclization of alkenes 4 led to benzofurans 7a-h, in an efficient synthetic approach to the benzofuran frame. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2377 / 2380
页数:4
相关论文
共 44 条
[1]   Phenolic constituents of Gnetum klossii [J].
Ali, Z ;
Tanaka, T ;
Iliya, I ;
Iinuma, M ;
Furusawa, M ;
Ito, T ;
Nakaya, K ;
Murata, J ;
Darnaedi, D .
JOURNAL OF NATURAL PRODUCTS, 2003, 66 (04) :558-560
[2]   FORMATION OF DIHYDROBENZOFURANS BY RADICAL CYCLIZATION [J].
BECKWITH, ALJ ;
MEIJS, GF .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (03) :136-137
[3]  
Bird C W., 1984, COMPREHENSIVE HETERO, P89
[4]  
Bishop BC, 1997, SYNTHESIS-STUTTGART, P1315
[5]  
Bosch J, 2000, SYNTHESIS-STUTTGART, P721
[6]  
BURKE JM, 1985, J CHEM RES-S, P34
[7]  
Cagniant P., 1975, Adv. Heterocycl. Chem., V18, P337, DOI DOI 10.1016/S0065-2725(08)60132-4
[8]   SYNTHETIC FUROCOUMARINS . XANTHOTOXIN AND METHYLXANTHOTOXINS [J].
DESOUZA, NJ ;
NAYAK, PV ;
SECCO, E .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1966, 3 (01) :42-&
[9]  
DONNELLY DMX, FURANS THEIR BENZO D
[10]   Recent developments in the chemistry of enaminones [J].
Elassar, AZA ;
El-Khair, AA .
TETRAHEDRON, 2003, 59 (43) :8463-8480