Synthesis and properties of new heterocyclic betaines: 4-Aryl-5(methoxycarbonyl)-2-oxo-3-(pyridin-l-ium-l-yl)-2,3-dihydro-lH- pyrrol-3-ides

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Abstract

New heterocyclic betaines, 4-aryl-5-(alkoxycarbonyl)-2-oxo-3-(pyridin-l-ium-l-yl)-2,3-dihydro-lH-pyrrol-3-ides, were synthesized in good yields by the reaction of alkyl 2H-azirine-2-carboxylates with 2-methoxy-2-oxo-l-(pyridin-l-ium-l-yl)ethan-l-ides, generated from the corresponding pyridinium salts. The betaines exist as the NH-tautomers both in solution and in the solid state. Two molecules of the betaine form a dimer by hydrogen bonds of the type N-H...O in solid state. According to TD DFT calculations the long-wave absorption band in betaines mainly corresponds to the intramolecular charge transfer between the negatively charged pyrrole unit and the positively charged pyridinium group. The blue shift of the long-wave absorption in protic solvents was adequately described in terms of H-complex formation with the nucleophilic centre of the molecular skeleton. (C) 2018 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)2466-2474
Number of pages9
JournalTetrahedron
Volume74
Issue number20
DOIs
Publication statusPublished - 17 May 2018

Scopus subject areas

  • Drug Discovery
  • Biochemistry
  • Organic Chemistry

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