[4 + 2] Annulation of 3-Nitroindoles with Alkylidene Malononitriles: Entry to Substituted Carbazol-4-amine Derivatives.

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ID: 175
2018
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Abstract
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.
Reference Key
cao2018[4 Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Cao, Dongdong;Ying, Anguo;Mo, Hanjie;Chen, Dingben;Chen, Gang;Wang, Zhiming;Yang, Jianguo;
Journal The Journal of organic chemistry
Year 2018
DOI
10.1021/acs.joc.8b01876
URL
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