ACYLATION AND CYCLODEHYDRATION OF BENZOFURAN-, BENZOTHIOPHENE-, AND INDOLYL-3-ACETIC ACID ARYLAMIDES. SYNTHESIS OF NOVEL BENZOFURO[2,3-<i>c</i>]-, BENZOTHIENO[2,3-<i>c</i>], AND INDOLO[2,3-<i>c<i>]PYRILIUM AND PYRIDINE DERIVATIVES

Authors

  • С. В. Толкунов L. M. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, Donetsk
  • В. С. Толкунов L. M. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, Donetsk
  • В. И. Дуленко L. M. Litvinenko Institute of Physical Organic and Coal Chemistry, National Academy of Sciences of Ukraine, Donetsk

Keywords:

2-acetylbenzo[b]thiophene-3-acetic acid arylamides, 2-acetylbenzo[b]furan-3-acetic acid arylamides, 2-acetylindolyl-3-acetic acid arylamides, 3-arylamino-1-methylhetero[2,3-c]pyrilium, N-aryl-1-methyl-3(2H)hetero[2,3-c]pyridones, cyclodehydration

Abstract

The acylation of benzo[b]furan-, benzo[b]thiophene, and indolyl-3-acetic acid arylamides using acetic anhydride in the presence of 70% perchloric acid occurs at the α-position of the heterocycle to give 2-acetylbenzo[b]furan-, 2-acetylbenzo[b]thiophene, and 2-acetylindolyl-3-acetic acid arylamides. Depending on the amount of perchloric used in the reaction they undergo cyclodehydration to 3-arylamino-1-methylhetero[2,3-c]pyrilium salts and to N-aryl-1-methyl-3(2H)hetero[2,3-c]pyridones.

How to Cite
Tolkunov, S. V.; Tolkunov, V. S.; Dulenko, V. I. Chem. Heterocycl. Compd. 2004, 40, 481. [Khim. Geterotsikl. Soedin. 2004, 577.]

For this article in the English edition, see DOI 10.1023/B:COHC.0000033542.86752.27

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Published

2004-04-25

Issue

No. 4 (2004)

Section

Original Papers