Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 1
41
Views
2
CrossRef citations to date
0
Altmetric
Original Articles

Novel Synthesis of Ethyl 3-(Bromoacetyl)-4,6-dichloro-1H-indole-2-carboxylate as Useful Intermediate in the Preparation of Potential Glycine Site Antagonists

&
Pages 51-60 | Received 29 May 1997, Published online: 20 Aug 2006

References and Notes

  • Collingridge , G. L. 1994 . The NMDA Receptor, , 2nd Ed. , Edited by: Watkins , J. C. Oxford, , England : IRL Press .
  • Palfreyman , M. G. and Baron , M. B. 1991 . Excitatory Amino Acid Antagonists , Edited by: Meldrum , B. 101 – 129 . Oxford, , England : Blackwell . Chapter 6
  • Kemp , J. A. and Leeson , P. D. 1993 . TiPS , 14 : 20
  • Leeson , P. D. and Iversen , L. L. 1994 . J. Med. Chem. , 37 : 4053
  • Johnson , J. W. and Ascher , P. 1987 . Nature , 325 : 529
  • Kleckner , N. W. and Dingledine , R. 1988 . Science , 241 : 835
  • Thompson , A. M. 1990 . Prog. Neurobiol. , 35 : 53
  • Huettner , J. E. 1991 . Biochem. Pharmacol , 41 : 9
  • Morris , R. G. M. , Anderson , E. , Lynch , G. S. and Baudry , M. 1986 . Nature , 319 : 774
  • Koek , W. and Colpaert , F. C. 1990 . J. Pharmacol. Exp. Ther. , 252 : 349
  • Chiamulera , C. , Costa , S. and Reggiani , A. 1990 . Psychopharmacol. , 112 : 551
  • Di Fabio , R. , Capelli , A. M. , Conti , N. , Cugola , A. , Donati , D. , Feriani , A. , Gastaldi , P. , Gaviraghi , G. , Hewkin , C. T. , Micheli , F. , Missio , A. , Mugnaini , M. , Pecunioso , A. , Quaglia , A. M. , Ratti , E. , Rossi , L. , Tedesco , G. , Trist , D. G. and Reggiani , A. 1997 . J. Med. Chem. , 40 : 841
  • Leeson , P. D. , Baker , R. , Carling , R. W. , Curtis , R. , Moore , K. W. , Williams , B. J. , Foster , A. C. , Donald , A. E. , Kemp , J. A. and Marshall , G. R. 1991 . J. Med. Chem. , 34 : 1243
  • Metzger , J. V. 1984 . “ Thiazole and their Benzo Derivatives ” . In Comprehensive Heterocyclic Chemistry , Edited by: Katritzky , A. R. and Rees , C. W. Vol. 6 , Pergamon Press . Chapter 4.19
  • Tanaka , K. , Nomura , K. , Oda , H. , Yoshida , S. and Mitsuhashi , K. 1991 . J. Heterocyclic. Chem. , 28 : 907
  • The acetylation of an unsbstituted indole 2-carboxylated ester, under Friedel-Crafts condition, was found to be dependent on the acidity of the carboxylic acid used; stronger acid derivatives tend to give the C-5 acylated product with respect to the acylation of C-3 position. Murakami Y. Tani M. Tanaka K. Yokoyama Y. Chem. Pharm. Bull. 1988 36 2023
  • Using carboxylic acid/ trifluoroacetic anhydride/ poliphosphoric acid method, stronger acid derivatives tend to give lower yield of the acetylated product. Murakami Y. Tani Suzuki M. Sudoh K. Uesato M. M. Tanaka K. Yokoyama Y. Chem. Pharm. Bull. 1985 33 4707
  • Dalla Croce , P. , Ferraccioli , R. and Ritieni , A. 1990 . Synthesis , : 212
  • After the conclusion of our work, an alternative procedure for the selective bromination of the α carbon of ethyl 3-acetyl-1H-indole-2-carboxylate has been published. Suzuki H. Shinpo K. Yamazaki T. Niwa S. Yokoyama Y. Murakami Y. Heterocycles 1996 42 83

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.