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

Libo Ruan; Min Shi; Shiwei Mao; Lifang Yu; Fan Yang; Jie Tang

doi:10.1016/j.tet.2013.12.050

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

Libo Ruan, Min Shi, Shiwei Mao, Lifang Yu, Fan Yang^*, Jie Tang

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

Research output: Contribution to journal › Article › peer-review

29 Scopus citations

Abstract

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 2-methoxydeoxybenzoins. 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.

Original language	English
Pages (from-to)	1065-1070
Number of pages	6
Journal	Tetrahedron
Volume	70
Issue number	5
DOIs	https://doi.org/10.1016/j.tet.2013.12.050
State	Published - 4 Feb 2014

Keywords

2-Arylbenzo[b]furans
2-Methoxychalcone epoxides
Cyclodehydration
Deformylation
Stemofuran A

Access to Document

10.1016/j.tet.2013.12.050

Cite this

@article{33095322aad64e3eaea2dcef2306f195,

title = "An efficient approach to construct 2-arylbenzo[b]furans from 2-methoxychalcone epoxides",

abstract = "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 2-methoxydeoxybenzoins. 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.",

keywords = "2-Arylbenzo[b]furans, 2-Methoxychalcone epoxides, Cyclodehydration, Deformylation, Stemofuran A",

author = "Libo Ruan and Min Shi and Shiwei Mao and Lifang Yu and Fan Yang and Jie Tang",

year = "2014",

month = feb,

day = "4",

doi = "10.1016/j.tet.2013.12.050",

language = "英语",

volume = "70",

pages = "1065--1070",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "5",

}

TY - JOUR

T1 - An efficient approach to construct 2-arylbenzo[b]furans from 2-methoxychalcone epoxides

AU - Ruan, Libo

AU - Shi, Min

AU - Mao, Shiwei

AU - Yu, Lifang

AU - Yang, Fan

AU - Tang, Jie

PY - 2014/2/4

Y1 - 2014/2/4

N2 - 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 2-methoxydeoxybenzoins. 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.

AB - 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 2-methoxydeoxybenzoins. 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.

KW - 2-Arylbenzo[b]furans

KW - 2-Methoxychalcone epoxides

KW - Cyclodehydration

KW - Deformylation

KW - Stemofuran A

UR - https://www.scopus.com/pages/publications/84892369021

U2 - 10.1016/j.tet.2013.12.050

DO - 10.1016/j.tet.2013.12.050

M3 - 文章

AN - SCOPUS:84892369021

SN - 0040-4020

VL - 70

SP - 1065

EP - 1070

JO - Tetrahedron

JF - Tetrahedron

IS - 5

ER -

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

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this