Faculty of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung City 807, Taiwan.
J Org Chem. 2009 Nov 20;74(22):8798-801. doi: 10.1021/jo9015634.
In this paper a concise, efficient, and environmentally benign method for the synthesis of 3-alkoxymethylcoumarin is described. From the reaction of 3-cyanochromene with an alkoxide and arylamine in THF, (Z)-2-phenylimino-3-alkoxymethylchromene was obtained as a novel intermediate via an isomerization of the double bond, a 1,2-addition of alkoxide, a Michael-type addition of aniline, an another isomerization of double bond and an elimination of ammonia. Subsequently, the intermediate was converted into the desired coumarin by treatment with 15% HCl in THF in good yield.
本文描述了一种简洁、高效且环境友好的 3-烷氧基甲基香豆素合成方法。通过 3-氰基色烯与烷氧基和芳胺在四氢呋喃中的反应，通过双键的异构化、烷氧基的 1,2-加成、苯胺的迈克尔加成、另一个双键的异构化和氨的消除，得到了 novel intermediate (Z)-2-苯基亚氨基-3-烷氧基甲基色烯。随后，通过用 15%盐酸在四氢呋喃中处理该中间体，以良好的收率得到了所需的香豆素。
