Stereoselective synthesis of novel functionalized cyclohexanone derivatives via the condensation of aromatic aldehydes with acetoacetamide and the influence of the ortho-effect and autocondensation

Vladimir L. Gein, Natalia V. Nosova, Andrei N. Yankin, Alina Y. Bazhina, Maksim V. Dmitriev

Research output

4 Citations (Scopus)

Abstract

A simple, inexpensive and stereoselective synthesis of novel functionalized cyclohexanone derivatives via the reaction of acetoacetamide with aromatic aldehydes in ethanol at room temperature is described. Additionally, the presence of substituents such as –NO 2 and –Cl in the ortho-position of the aldehyde aromatic ring resulted in the formation of novel piperidines. The use of Lewis acids such as iron(III) chloride and bismuth(III) nitrate as catalysts led to autocondensation of acetoacetamide and the formation of 2,4-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxamide.

Original languageEnglish
Pages (from-to)1592-1596
Number of pages5
JournalTetrahedron Letters
Volume60
Issue number24
DOIs
Publication statusPublished - 13 Jun 2019

Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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