Xu Chuangchuang, Xu Jiaxi
State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science , Beijing University of Chemical Technology , Beijing 100029 , People's Republic of China.
J Org Chem. 2018 Dec 7;83(23):14733-14742. doi: 10.1021/acs.joc.8b02203. Epub 2018 Nov 15.
A convenient synthetic method to indoles from anilines and cyanoepoxides was developed under the catalysis of BF·OEt or AlCl in alcohols. The reaction involves a tandem reaction of the regiospecific ring-opening of cyanoepoxides with anilines, elimination of cyanide, intramolecular aromatic electrophilic substitution, and water elimination. The Lewis acid generated protic acid is an efficient catalyst. The method features readily accessible starting materials, wide substrate scope, transition-metal-free environment, and regiospecificity in the ring-opening of cyanoepoxides.
在醇类溶剂中，以BF·OEt或AlCl为催化剂，开发了一种从苯胺和氰基环氧化物方便合成吲哚的方法。该反应涉及氰基环氧化物与苯胺的区域选择性开环、氰化物消除、分子内芳香亲电取代和脱水的串联反应。路易斯酸产生的质子酸是一种有效的催化剂。该方法具有起始原料易于获得、底物范围广、无过渡金属环境以及氰基环氧化物开环的区域选择性等特点。
