A SYNTHESIS OF POLYFUNCTIONALLY SUBSTITUTED CARBO- AND HETEROCYCLIC COMPOUNDS BASED ON A REACTION OF ETHYL ARYLMETHYLIDENECYANOACETATE WITH ACETOACETIC ACID N-ARYLAMIDES

Authors

  • Anush Khachatryan Senior science employee
  • Anush Sargsyan Scientific – Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 26 Azatutyan Ave., Yerevan 0014 https://orcid.org/0000-0002-0303-0710
  • Katya Avagyan Scientific – Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 26 Azatutyan Ave., Yerevan 0014
  • Anahit Simonyan 1 Scientific – Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 26 Azatutyan Ave., Yerevan 0014 https://orcid.org/0009-0003-3868-4022
  • Angin Zohrabyan Scientific – Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 26 Azatutyan Ave., Yerevan 0014 https://orcid.org/0009-0007-6572-1174
  • Henrik Panosyan Scientific – Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 26 Azatutyan Ave., Yerevan 00 https://orcid.org/0000-0001-8311-6276
  • Alik Badasyan Scientific – Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 26 Azatutyan Ave., Yerevan 0014 https://orcid.org/0009-0003-6123-9867

Keywords:

acetoacetic acid N-arylamides, ethyl arylmethylidene cyanoacetate, Michael adduct, intramolecular cyclization, regioselectivity, retro-Michael reaction

Abstract

The reaction of ethyl arylmethylidenecyanoacetate with acetoacetic acid N-arylamides was studied. It was revealed that in the presence of catalysts (triethylamine, piperidine) in ethanol (acetonitrile), the dominant direction of the reaction was the formation of the products of the retro-Michael reaction, new oxocyclohexane-1,3-dicarboxamide derivatives. It was established that, along with carbocyclization, an intramolecular heterocyclization of the Michael adduct at the nitrile group was also realized with the formation of previously unknown ethyl 5-acetyl-1,4-diaryl-2-imino-6-oxo-piperidine-3-carboxylates and ethyl 5-acetyl-2-amino-1,4-diaryl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylates. The antibacterial activity of some of the obtained compounds was investigated.

Published

2026-05-15

Issue

Vol. 61 No. 11/12 (2025)

Section

Original Papers