CYCLIZATION OF SUBSTITUTED (2-PYRIDYLTHIO)PHENYLACETIC ACIDS AND CHROMATICITY OF MESOIONIC THIAZOLO[3,2-<i>a</i>]PYRIDINIUM-3-OLATES

Authors

  • К. В. Федотов Institute of Organic Chemistry, National Academy of Sciences of Ukraine
  • Т. П. Шумейко Institute of Organic Chemistry, National Academy of Sciences of Ukraine
  • Н. Н. Романов Institute of Organic Chemistry, National Academy of Sciences of Ukraine
  • А. И. Толмачев Institute of Organic Chemistry, National Academy of Sciences of Ukraine
  • А. Я. Ильченко Institute of Organic Chemistry, National Academy of Sciences of Ukraine

DOI:

https://doi.org/10.1007/1522

Keywords:

3-imino-2-phenyl-2, 3-dihydrothieno[2, 3-b]pyridine-2-carboxylic acid, mesoionic compounds, (2-pyridylthio)phenylacetic acids, thiazolo[3, 2-a]pyridinium-3-olates, absorption spectra

Abstract

The cyclization of substituted (2-pyridylthio)phenylacetic acids has been studied. It was established that reaction occurs at two reaction centers with the formation of substituted 3-imino-2-phenyl-2,3-dihydrothieno[2,3-b]pyridine-2-carboxylic acids and substituted mesoionic thiazolo[3,2-a]pyridinium-3-olates. The direction of cyclization is influenced by the acidity of the medium and the character of the substituents in the pyridine nucleus. The spectral properties of the synthesized mesoionic compounds were investigated
experimentally and theoretically (by the Pariser–Parr–Pople method).

Authors: K. V. Fedotov, T. P. Shumeiko, N. N. Romanov,
A. I. Tolmachev, and A. Ya. Ilchenko

English Translation in Chemistry of Heterocyclic Compounds, 2011, 47 (5), pp 622-630

http://link.springer.com/article/10.1007/s10593-011-0807-z

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Published

2014-01-22

Issue

No. 5 (2011)

Section

Original Papers