Facile two-step synthesis of 2-arylbenzofurans based on the selective cross McMurry couplings

被引:89
作者
Duan, Xin-Fang [1 ]
Zeng, Jing [1 ]
Zhang, Zhan-Bin [1 ]
Zi, Guo-Fu [1 ]
机构
[1] Beijing Normal Univ, Dept Chem, Beijing 100875, Peoples R China
关键词
D O I
10.1021/jo7019652
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A novel two-step synthesis of 2-arylbenzofurans has been developed. It involves a selective cross McMurry coupling of a salicylaldehyde or substituted salicylaldehyde with an aromatic aldehyde and a sequential oxidative cyclization of the resulting ortho-vinylphenols. Utilizing this synthetic protocol, a variety of 2-arylbenzofurans including cicerfuran (5) have been efficiently synthesized.
引用
收藏
页码:10283 / 10286
页数:4
相关论文
共 43 条
[1]   Synthesis of cicerfuran, an antifungal benzofuran, and some related analogues [J].
Aslam, SN ;
Stevenson, PC ;
Phythian, SJ ;
Veitch, NC ;
Hall, DR .
TETRAHEDRON, 2006, 62 (17) :4214-4226
[2]  
BANERJI A, 1990, CHEM COMMUN, P150
[3]   Gold-catalyzed tandem cycloisomerization-hydroalkoxylation of homopropargylic alcohols [J].
Belting, Volker ;
Krause, Norbert .
ORGANIC LETTERS, 2006, 8 (20) :4489-4492
[4]  
Cagniant P., 1975, Adv. Heterocycl. Chem., V18, P337, DOI DOI 10.1016/S0065-2725(08)60132-4
[5]   REACTION OF ORTHO ALKENYL PHENOLS AND ALKYLPHENOLS WITH 2,3-DICHLORO-5,6-DICYANOBENZOQUINONE (DDQ) - SYNTHESES OF 2,2-DIALKYLCHROMENES [J].
CARDILLO, G ;
CRICCHIO, R ;
MERLINI, L .
TETRAHEDRON, 1971, 27 (10) :1875-&
[6]   On-water chemistry:: Copper-catalyzed straightforward synthesis of benzo[b]furan derivatives in neat water [J].
Carril, M ;
SanMartin, R ;
Tellitu, I ;
Domínguez, E .
ORGANIC LETTERS, 2006, 8 (07) :1467-1470
[7]   Synthesis of benzo[b]furans via CuI-catalyzed ring closure [J].
Chen, CY ;
Dormer, PG .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17) :6964-6967
[8]   Synthesis of sterically hindered ortho-substituted tetraphenylethenes. Electronic effects in the McMurry olefination reaction [J].
Chung, MK ;
Qi, GZ ;
Stryker, JM .
ORGANIC LETTERS, 2006, 8 (07) :1491-1494
[9]   A new, expeditious entry to the benzophenanthrofuran framework by a Pd-catalyzed C- and O-arylation/PIFA-mediated oxidative coupling sequence [J].
Churruca, F ;
SanMartin, R ;
Tellitu, I ;
Domínguez, E .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (12) :2481-2490
[10]  
Dell C. P., 2000, SCI SYNTHESIS HOUBEN, V10, P11