文章基本信息

标题：Revisiting 2-Alkoxy-3-bromoindolines: Control C-2 vs. C-3 Elimination for Regioselective Synthesis of Alkoxyindoles
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作者：Takumi Abe ; Yuta Kosaka ; Takaaki Kawasaki 等
期刊名称：Chemical and Pharmaceutical Bulletin
印刷版ISSN：0009-2363
电子版ISSN：1347-5223
出版年度：2020
卷号：68
期号：6
页码：555-558
DOI：10.1248/cpb.c20-00135
出版社：The Pharmaceutical Society of Japan
摘要：The regioselective synthesis of both 2- and 3-alkoxyindoles from a common intermediate, 2-alkoxy-3-bromoindolines (ROBIN), is described. The 2-alkoxyindoles are obtained by a base-promoted regioselective elimination of HBr from ROBIN, whereas the synthesis of 3-alkoxyindoles is achieved by a silver-mediated alkoxylation followed by an acid-promoted elimination of alkoxide. This key elimination features the complete regioselectivity and no need for catalysts, that makes it have potential synthetic applications. Furthermore, this protocol is user friendly because ROBIN is able to be prepared from commercially available indoles and is a bench-stable easy-to-handle crystalline substrate, thus allowing the concise synthesis of a variety of both 2- and 3-alkoxyindoles.
关键词：3-alkoxyindole;2-alkoxyindole;elimination;regioselective synthesis;silver