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Synthesis 2002(16): 2426-2430
DOI: 10.1055/s-2002-35228
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthetic Applications of Aminochlorocarbenes: A Two-step Conversion of N-Methylformanilides into 3-Arylamino-2-chloroindoles

Ying Cheng*a, Yu-Hua Zhana, Hai-Xia Guana, Hua Yanga, Otto Meth-Cohn*b
Chemistry Department, Beijing Normal University, Beijing 100875, China
e-Mail: yincheng@95777.com;
Chemistry Department, University of Sunderland, Sunderland SR1 3SD, UK
e-Mail: otto.meth-cohn@sunderland.ac.uk;
Further Information

Publication History

Received 29 July 2002
Publication Date:
04 November 2002 (online)

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Abstract

The thermal cyclisation of 1,2-diarylamino-1,2-dichloroethenes (dimers of arylaminochlorocarbenes) in DMF affords 3-arylamino-2-chloroindoles in good yields (70-91%).

Key words

cyclisation - 1,2-diarylamino-1,2-dichloroethenes - aryl­aminochlorocarbenes - 3-arylamino-2-chloroindoles

    References

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  • 1b Cheng Y. Goon S. Meth-Cohn O. J. Chem. Soc., Perkin Trans. 1  1998,  1619 
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  • (b) Velezheva VS. Ryabova SYu. Chem. Heterocycl. Compd.  1990,  617 
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  • 4 Sundberg RJ. In Indoles   Meth-Cohn O. Academic Press; London: 1996.  p.39-41  ; and references therein