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

Ying Cheng; Hai-Ling Ye; Yu-Hua Zhan; Otto Meth-Cohn

doi:10.1055/s-2001-13405

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Synthesis 2001(6): 0904-0908
DOI: 10.1055/s-2001-13405

PAPER

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 Ye^a, Yu-Hua Zhan^a, 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)

Abstract
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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

References

1a Erdmann OL. J. Prakt. Chem. 1840, 22: 321

Google Scholar
1b Erdmann OL. J. Prakt. Chem. 1841, 22: 257

Google Scholar
1c Erdmann OL. J. Prakt. Chem. 1841, 24: 1

Google Scholar
2a Laurent A. Ann. Chim. Phys. 1840, 3: 372

Google Scholar
2b Laurent A. Ann. Chim. Phys. 1840, 3: 469

Google Scholar
2c Laurent A. J. Prakt. Chem. 1842, 25: 434

Google Scholar
3a Kapadia GJ. Shukala YN. Planta Med. 1993, 59: 568

Crossref Google Scholar
3b Glover V. Halket JM. Watkins PJ. Clow A. Goodwin BL. Sandler MJ. Neurochem. 1988, 51: 656

Crossref Google Scholar
3c Kapadia GJ. Shukala YN. Basak SP. Sokoloski EA. Fales HM. Tetrahedron 1980, 36: 2441

Crossref Google Scholar
4 Breinholt J. Demuth H. Heide M. Jensen GW. Moller IL. Nielson RI. Olsen CE. Rosendahl CN. Acta. Chem. Scand. 1996, 50: 443 ; and references cited therein

Google Scholar
5 Norman TR. Med. Sci. Res. 1996, 3: 153; and references cited therein

Google Scholar
6 Pang FY. Huckerbridge FH. Forster G. Tan K. Clow A. Stress. Med. 1996, 12: 35; and references cited therein

Crossref Google Scholar
7 Pfitzinger W. J. Prakt. Chem. 1886, 33: 100

Crossref Google Scholar
8a Holt SJ. Petrow V. J. Chem. Soc. 1947, 607

Google Scholar
8b Degutis YA. Ezyarskaite AB. Chem. Heterocycl. Compd. (Engl. Trans.) 1988, 22: 1114

Google Scholar
9 Popp FD. Adv. Heterocycl. Chem. 1975, 18: 2

Google Scholar
10 Hewawasam P. Meanwell NA. Tetrahedron Lett. 1994, 35: 7303

Crossref Google Scholar
11a Nohara F. inventors; Jpn. Kokai Tokkyo Koho 8013227.
11c Fothergill A, and Osbond JM. inventors; Eur. Patent 30380.
12 Meth-Cohn O. Goon S. Tetrahedron Lett. 1996, 37: 9381

Crossref Google Scholar
13 Cheng Y. Liu QX. Meth-Cohn O. Tetrahedron Lett. 2000, 41: 3475

Crossref Google Scholar
14a Tüzün C. Ogliaruso M. Becker EI. Org. Synth. Coll. Vol. 5 111,

Google Scholar
14b Staudinger H. Stockmann M. Ber. Dtsch. Chem. Ges. 1909, 42: 3489

Google Scholar
15 Heller G. Ber. Dtsch. Chem. Ges. 1926, 59: 710

Google Scholar
See for example:
16a Staudinger H. Stockmann M. Ber. Dtsch. Chem. Ges. 1909, 42: 3492

Article in Thieme Connect Google Scholar
16b Yietze LF. Schneider C. Pretor M. Synthesis 1993, 1079

Article in Thieme Connect Google Scholar
17 Goto J. Komatsu S. Goto N. Nambara T. Chem. Pharm. Bull. 1981, 29: 1899

Google Scholar