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

详细信息    查看全文

• 作者：V.S. Prasada Rao Lingam ; Dnyaneshwar H. Dahale ; Kagga Mukkanti ; Balasubramanian Gopalan ; Abraham Thomas
• 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
• 刊名：Tetrahedron Letters
• 出版年：2012
• 出版时间：17 October, 2012
• 年：2012
• 卷：53
• 期：42
• 页码：5695-5698
• 全文大小：463 K

文摘

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 ¦Á- or ¦Â-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.