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Chemistry of Heterocyclic Compounds

, Volume 41, Issue 4, pp 515–525 | Cite as

Reaction of 3-Arylaminobenzofuro-, 3-Arylaminobenzothieno-, and 3-Arylaminoindolo[2,3-c]pyrylium Salts with Nucleophilic Reagents

  • V. S. Tolkunov
  • Yu. B. Vysotsky
  • O. A. Gorban’
  • S. V. Shishkina
  • O. V. Shishkin
  • V. I. Dulenko
Article

Abstract

We have studied the reactions of 3-arylaminobenzofuro-, 3-arylaminobenzothieno-, and 3-arylaminoindolo[2,3-c]pyrylium salts with ammonium acetate, primary amines, and hydrazine hydrate. In an alcoholic medium, primary amines and hydrazine hydrate open up the pyrylium ring to form arylamides of 2-(N-benzylmethylketimine)hetaryl-3-acetic acids or the corresponding hydrazones, where further heterocyclization does not occur. Upon treatment with ammonium acetate in acetic acid, 2-aryl-1-methylhetero[2,3-c]pyridin-3-(2H)-ones are formed along with their 2-unsubstituted analogs.

Keywords

3-arylaminobenzothieno[2,3-c]pyrylium 3-arylaminobenzofuro[2,3-c]pyrylium 3-arylaminoindolo[2,3-c]pyrylium 2-N-aryl-1-methylhetero[2,3-c]pyridin-3(2H)-ones recyclization 

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Copyright information

© Springer Science+Business Media, Inc. 2005

Authors and Affiliations

  • V. S. Tolkunov
    • 1
  • Yu. B. Vysotsky
    • 2
  • O. A. Gorban’
    • 1
  • S. V. Shishkina
    • 3
  • O. V. Shishkin
    • 3
  • V. I. Dulenko
    • 1
  1. 1.L. M. Litvinenko Institute of Physical-Organic and Coal ChemistryNational Academy of Sciences of UkraineDonetskUkraine
  2. 2.Donbass State Academy of Construction and ArchitectureMakeevkaUkraine
  3. 3.Institute for Single CrystalsNational Academy of Sciences of UkraineKharkovUkraine

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