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Synthesis 2001(6): 0904-0908
DOI: 10.1055/s-2001-13405
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Very Simple Route to N-Methylisatins: Friedel-Crafts Acylation of p-Substituted N,N-Dimethylanilines with Oxalyl Chloride and DABCO

Ying Cheng*a, Hai-Ling Yea, Yu-Hua Zhana, Otto Meth-Cohn*b
a Chemistry Department, Beijing Normal University, Beijing 100875, China
b Chemistry Department, University of Sunderland, Sunderland SR1 3SD, UK
e-Mail: yincheng@public2.east.net.cn; e-Mail: otto.meth-cohn@sunderland.ac.uk;
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Publication History

Received 5 December 2000
Publication Date:
24 September 2004 (online)

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Abstract

N-Methylisatins were obtained in high yields in a one-pot reaction by the Friedel-Crafts acylation of p-substituted N,N-dimethylanilines by oxalyl chloride in the presence of a base. The best results were obtained using DABCO.

Key words

isatins - Friedel-Crafts acylation - condensations - amines - cyclizations