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A Simple and Efficient Access to Naphtho[ b ]furans by Claisen Rearrangement/Cyclization of Bromonaphthyl 3‐Phenylallyl Ethers
Author(s) -
Wang Wei,
Huang Jin,
Zhou Rong,
Jiang ZhiJie,
Fu HaiYan,
Zheng XueLi,
Chen Hua,
Li RuiXiang
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500151
Subject(s) - chemistry , claisen rearrangement , base (topology) , solvent , combinatorial chemistry , medicinal chemistry , organic chemistry , mathematical analysis , mathematics
A transition‐metal‐free Claisen rearrangement/cyclization reaction was developed for the synthesis of naphthofuran derivatives from bromonaphthyl 3‐phenylallyl ethers. The nature of the base employed in this reaction plays an important role in determining the ratio for the formation of naphthofuran and naphthol products. By using K 2 CO 3 as base and DMF as solvent, we have synthesized a variety of functionalized naphthofurans in good to high yields (49–92 %) and with satisfactory selectivities.