ACYLATING AND ARYLSULFONYLATING ABILITY OF O-DERIVATIVES OF ISATIN 3-OXIMES

Authors

  • А. П. Станкявичюс Institute of Cardiology, Kaunas Medical University, Kaunas 50009
  • П. Б. Терентьев M. V. Lomonosov Moscow State University, Moscow 119899
  • Л. Н. Янушене Institute of Cardiology, Kaunas Medical University, Kaunas 50009
  • А. Б. Савицкас Kaunas Medical University, Kaunas 44307

DOI:

https://doi.org/10.1007/8409

Keywords:

O-acetates, O-benzoates, and O-arylsulfonates of 2, 3-indoledione 3-oximes, acylation and arylsulfonation, mass spectrometry

Abstract

O-Acyl and O-arylsulfonyl derivatives of isatin 3-oximes have been synthesized and their interaction with alcohols and amines has been investigated. It was established that none of the esters of 1-substituted isatin 3-oximes reacted with the  indicated nucleophiles. 1-Unsubstituted O-aryl and O-arylsulfonyl derivatives react with amines as acylating agents even at room temperature, but O-acetyl derivatives only on heating. Acylamides or arylsulfamides respectively are formed  in this way. O-Acyl derivatives do not react with alcohols at room temperature. Only O-benzoyl derivatives form ethyl benzoate on heating in ethanol. A comparative analysis of mass spectrometric data on the processes of acylation and arylsulfonylation is given.

How to Cite
Stankevicius, A. P.; Terentiev, P. B.; Janushene, L. N.; Savickas, A. B.  Chem. Heterocycl. Compd. 2005, 41, 98. [Khim. Geterotsikl. Soedin. 2005, 113.]

For this article in the English edition, see DOI 10.1007/s10593-005-0114-7

 

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Published

2023-12-05

Issue

No. 1 (2005)

Section

Original Papers