Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 20, Pages 12568-12574Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01876
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Funding
- Natural Science foundation of Zhejiang Province [LY18B020002, LQ15B020001]
- National Natural Science Foundation of China [21576176]
- PhD Start-up Grant, Nurturing Project from Taizhou University [2017PY008]
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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.
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