An efficient approach to construct 2-arylbenzo[b]furans from 2-methoxychalcone epoxides

被引：27
|
作者：
Ruan, Libo [1 ]
Shi, Min [1 ]
Mao, Shiwei [1 ]
Yu, Lifang [1 ]
Yang, Fan [1 ]
Tang, Jie [1 ]
机构：
[1] E China Normal Univ, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, Inst Drug Discovery & Dev, Shanghai 200062, Peoples R China
来源：
TETRAHEDRON | 2014年 / 70卷 / 05期
关键词：
2-Arylbenzo[b]furans; 2-Methoxychalcone epoxides; Deformylation; Cyclodehydration; Stemofuran A; ONE-POT SYNTHESIS; O-IODOPHENOLS; 2-ARYLBENZOFURANS; ARYL; DERIVATIVES; REARRANGEMENT; ANTIOXIDANT; BENZOFURANS; IODIDES; LIGNANS;
D O I：
10.1016/j.tet.2013.12.050
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient and practical method for construction of 2-arylbenzo[b]furans from 2-methoxychalcone epoxides has been reported. Catalyzed by 2 mol % of BF3.Et2O, 2-methoxychalcone epoxides went through the Meerwein rearrangement, followed by deformylation in one-pot to successfully afforded 2methoxydeoxybenzoins. Afterward, 2-arylbenzo[b]furans were obtained in high yields (87%-100%) via intermolecular cyclodehydration of 2-methoxydeoxybenzoins with 48% HBr. By utilization of this approach, the natural product stemofuran A and the key intermediate of eupomatenoid 6 have been synthesized conveniently. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1065 / 1070
页数：6
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