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
收藏
页码：5695 / 5698
页数：4
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