REACTION OF 3-ARYLAMINOBENZOFURO-, 3-ARYLAMINOBENZOTHIENO-, AND 3-ARYLAMINOINDOLO[2,3-<i>c</i>]PYRYLIUM SALTS WITH NUCLEOPHILIC REAGENTS

Authors

  • В. С. Толкунов L. M. Litvinenko Institute of Physical-Organic and Coal Chemistry, National Academy of Sciences of Ukraine, Donetsk 83114
  • Ю. Б. Высоцкий Donbass State Academy of Construction and Architecture, Makeevka 86128
  • О. А. Горбань L. M. Litvinenko Institute of Physical-Organic and Coal Chemistry, National Academy of Sciences of Ukraine, Donetsk 83114
  • С. В. Шишкина Institute for Single Crystals, National Academy of Sciences of Ukraine, Kharkov 310001
  • О. В. Шишкин Institute for Single Crystals, National Academy of Sciences of Ukraine, Kharkov 310001
  • В. И. Дуленко L. M. Litvinenko Institute of Physical-Organic and Coal Chemistry, National Academy of Sciences of Ukraine, Donetsk 83114

DOI:

https://doi.org/10.1007/8333

Keywords:

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

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.

How to Cite
Tolkunov, V. S.; Vysotsky, Yu. B.; Gorban', O. A.; Shishkina, S. V.; Shishkin, O. V.; Dulenko, V. I.  Chem. Heterocycl. Compd. 2005, 41,515. [Khim. Geterotsikl. Soedin. 2005, 601.]

For this article in the English edition, see DOI 10.1007/s10593-005-0181-9


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Published

2023-11-17

Issue

No. 4 (2005)

Section

Original Papers