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Synthesis 2003(3): 0383-0388
DOI: 10.1055/s-2003-37354
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (Indol-3-yl)methanesulfonamide and its 5-Methoxy Derivative

Alexander M. Korolev, Andrey E. Shchekotikhin, Ludmila N. Lysenkova, Maria N. Preobrazhenskaya*
Gause Institute of New Antibiotics, Russian Academy of Medical Sciences, B. Pirogovskaya 11, Moscow 119021, Russia
Fax: +7(095)2450295; e-Mail: lcta@space.ru;
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Publication History

Received 5 November 2002
Publication Date:
19 February 2003 (online)

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Abstract

Two methods for the synthesis of (indol-3-yl)methanesulfonamide were elaborated based on the ‘switching off’ the reactivity of the indole nucleus in the intermediates by using indoline or indoxyl compounds. (2,3-Dihydroindol-3-yl)methanesulfonic acid was the key compound used in the indole-indoline approach and (1-acetyl-3-hydroxy-2,3-dihydroindol-3-yl)-N-(tert-butyl)methanesulfonamide was the key intermediate when 1-acetylindoxyl was used as the starting compound.

Key words

(indol-3-yl)methanesulfonamide - sodium (indol-3-yl)methanesulfonate - indoxyl - (N-tert-butyl)methanesulfonamide - (5-methoxyindol-3-yl)methanesulfonamide

    References

  • 1 Silverman RB. The Organic Chemistry of Drug Design and Drug Action   Academic Press; San Diego: 1992. 
    Google Scholar
  • 2a Iskric S. Period. Biol.  1984,  86:  153 
    Google Scholar
  • 2b Kulmacz RJ. J. Biol. Chem.  1989,  264:  14136 
    Google Scholar
  • 3 Connor HE. Beattie DT. Migraine: Pharmacology and Genetics   Sandler M. Ferrary M. Harnett S. Chapman and Hall; London: 1996.  p.30 
    Google Scholar
  • 4 Wieland T. Fischer E. Moewus F. Liebigs Ann. Chem.  1949,  561:  47 
    Google Scholar
  • 5 Coker N. J. Org. Chem.  1962,  27:  1881 
    Google Scholar
  • 6 Thompson ME. J. Org. Chem.  1984,  49:  1700 
    Google Scholar