Microwave-assisted Claisen rearrangement of naphthyl 2-propynyl ethers: synthesis of naphthofurans

被引：24

作者：

Lingam, V. S. Prasada Rao ^{[1
]}

Dahale, Dnyaneshwar H. ^{[1
]}

Mukkanti, Kagga ^{[2
]}

Gopalan, Balasubramanian ^{[1
]}

Thomas, Abraham ^{[1
]}

机构：

[1] Glenmark Pharmaceut Ltd, MIDC, Glenmark Res Ctr, Div Med Chem, Navi Mumbai 400709, India

[2] Jawaharlal Nehru Technol Univ Hyderabad, Inst Sci & Technol, Hyderabad 500072, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 42期

关键词：

Naphtho[1,2-b]furans; Naphtho[2,1-b]furans; Naphthyl 2-propynyl ethers; Claisen rearrangement; Cesium fluoride; Mitsunobu reaction; Microwave irradiation; ARYL PROPARGYL ETHER; CONSTITUENTS; FURANS;

D O I：

10.1016/j.tetlet.2012.08.053

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient two-step approach for the synthesis of naphtho[1,2-b]furans and naphtho[2,1-b]furans has been developed. Various functionalized propargyl alcohols were etherified with alpha- or beta-naphthol under Mitsunobu reaction conditions to give naphthyl 2-propynyl ethers, which underwent a facile microwave-assisted Claisen rearrangement and concomitant anionic cyclization to yield naphthofuran derivatives under basic reaction conditions. (c) 2012 Elsevier Ltd. All rights reserved.

引用

页码：5695 / 5698

页数：4

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