Interaction of arylglyoxals with thioureas

Authors

  • Andrey A. Anishchenko Oles Honchar Dnipropetrovsk National University, 72, Gagarin Ave., Dnipropetrovsk 49010, Ukraine
  • Vitaliy V. Volosyuk Oles Honchar Dnipropetrovsk National University, 72, Gagarin Ave., Dnipropetrovsk 49010, Ukraine
  • Viktor V. Shtamburg National Technical University “Kharkiv Polytechnic Institute”, Ukraine
  • Alexandr V. Mazepa A.V. Bogatsky Physico-Chemical Institute of the National academy of sciences of Ukraine, Ukraine

DOI:

https://doi.org/10.15421/081411

Keywords:

2-thiohydantoine, arylglyoxals, thiazolidinone

Abstract

Literature data about the reaction of arylglyoxals with  thiourea has been discussed. It has been shown that no systematic studies in this issue had ever been carried out, furthermore some data is contradictory. The reaction of arylglyoxals with thiourea is reported to be a stepwise process that depends on at least two factors. It is reaction conditions such as temperature and solvent. Also the nature of glyoxal may have crucial influence on the structure of products. In this article has been provided the convincing evidence of formation three different kinds of heterocyclic systems upon reaction of p-substituted phenylglyoxals with N-methyl and N-phenylthiourea.

Author Biographies

Andrey A. Anishchenko, Oles Honchar Dnipropetrovsk National University, 72, Gagarin Ave., Dnipropetrovsk 49010

Associate Professor, Organic Chemistry Department, PhD in Organic Chemistry

Vitaliy V. Volosyuk, Oles Honchar Dnipropetrovsk National University, 72, Gagarin Ave., Dnipropetrovsk 49010

Аспирант кафедры органической химии

References

Schubert, M. P. Combination of thiol acids with methylglyoxal. J. Biol. Chem., 1935, Vol. 111, p. 671–678.

McKay, W. R., Proctor, G. R. Removal of toluene-p-sulphonyl groups from sulphonamides. Part 5. Reactions of phenylglyoxal imines and some tosylimines. J. Chem. Soc., Perkin Trans. 1, 1981, p. 2443–2450.

Paul, S., Gupta, M., Gupta, R., Loupy, A. Microwave Assisted Synthesis of 1,5-Disubstituted Hydantoins and Thiohydantoins in Solvent-Free Conditions. Synthesis, 2002, p. 75–78.

Ettari, R., Pinto, A., Micale, N. Synthesis and anti-HIV activity evaluation of new phenyl ethyl thiourea (PET) derivatives. ARCIVOC, 2009, p. 227–234.

Anishchenko, A. A., Shtamburg, V. G., Volosyuk, V. V., Olefir, D. A., Mazepa, A. V. Condensation of p-chlorophenylglyoxal with phenylthiourea. Visn. Dnipropetr. Univ.: Khim., 2012, vol. 20, no. 18, p. 110–112. [in Russian]

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Published

2014-12-02

Issue

Vol. 22 No. 1 (2014): Bulletin of Dnipropetrovsk University. Series Chemistry

Section

Organic Chemistry

License

Copyright (c) 2014 Oles Honchar Dnipropetrovsk National University

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