Cao Dongdong, Ying Anguo, Mo Hanjie, Chen Dingben, Chen Gang, Wang Zhiming, Yang Jianguo
School of Pharmaceutical and Chemical Engineering , Taizhou University , Taizhou 318000 , P.R. China.
College of Pharmaceutical Science , Zhejiang Chinese Medical University , Hangzhou 311400 , P.R. China.
J Org Chem. 2018 Oct 19;83(20):12568-12574. doi: 10.1021/acs.joc.8b01876. Epub 2018 Oct 4.
A general and transition-metal-free method for the construction of the carbazol-4-amine motif via a vinylogous Michael addition/cyclization/isomerization/elimination reaction of 3-nitroindoles with alkylidene malononitriles has been developed. This novel methodology allows the facile synthesis of a series of di- and trisubstituted carbazol-4-amine derivatives in moderate to good yields. A gram-scale experiment was successfully performed, highlighting the practicability of this method. Moreover, this strategy is also applicable to 3-nitrobenzothiophene, affording the corresponding dibenzo[ b, d]thiophen-1-amine derivatives in moderate yields.
通过3-硝基吲哚与亚烷基丙二腈的烯醇式迈克尔加成/环化/异构化/消除反应构建咔唑-4-胺基序的通用且无过渡金属的方法已被开发出来。这种新颖的方法能够以中等至良好的产率轻松合成一系列二取代和三取代的咔唑-4-胺衍生物。成功进行了克级实验，突出了该方法的实用性。此外，该策略也适用于3-硝基苯并噻吩，能以中等产率得到相应的二苯并[b,d]噻吩-1-胺衍生物。
