Synthesis, Experimental and Computational Spectroscopic Studies, and Formation Thermodynamics of Diethyl [[2-(1-Aryl-4,5-dihydro-1H-imidazol- 2-yl)hydrazinyl]methylene]propanedioates

ISSN: 1875-6255 (Online)
ISSN: 1570-1786 (Print)


Volume 11, 10 Issues, 2014


Download PDF Flyer




Letters in Organic Chemistry

Aims & ScopeAbstracted/Indexed in


Submit Abstracts Online Submit Manuscripts Online

Editor-in-Chief:
Miguel Yus
Universidad de Alicante Apdo
Alicante
Spain


View Full Editorial Board

Subscribe Purchase Articles Order Reprints

Current: 0.648
5 - Year: 0.665

Synthesis, Experimental and Computational Spectroscopic Studies, and Formation Thermodynamics of Diethyl [[2-(1-Aryl-4,5-dihydro-1H-imidazol- 2-yl)hydrazinyl]methylene]propanedioates

Author(s): Agnieszka A. Kaczor, Monika Aleta ska-Kozak, Tomasz Wrobel and Dariusz Matosiuk

Affiliation: Department of Synthesis and Chemical Technology of Pharmaceutical Substances with Computer Modeling Lab, Faculty of Pharmacy with Division of Medical Analytics, Medical University of Lublin, 4A Chod zki St., PL-20093 Lublin, Poland.

Abstract

We present experimental and computational studies on the pseudo-Michael reaction of (E)-1-aryl-2-hydrazinyl- 4,5-dihydro-1H-imidazoles with diethyl (ethoxymethylene)malonate (DEEM). The pseudo-Michael reaction leads to chain adducts, i.e. diethyl [[2-(1-aryl-4,5-dihydro-1H-imidazol-2-yl)hydrazinyl]methylene]propanedioates. This result is in contrast to our earlier studies on the pseudo-Michael reaction of DEEM with 1-aryl-4,5-dihydro-1H-imidazol-2-amines which results in imidazo[1,2-α]pyrimidine derivatives even at low temperature without the possibility of isolating chain intermediates. The structure of all the compounds is confirmed with experimental and computational spectroscopy (1H and 13C NMR, IR, MS). Furthermore, thermodynamics of the reaction and HOMO-LUMO of the reactants are studied by using of quantum chemical calculations.




Keywords: Diethyl (ethoxymethylene)malonate, Michael reaction, quantum chemical calculations.

Purchase Online Rights and Permissions

  
  



Article Details

Volume: 11
Issue Number: 7
First Page: 493
Last Page: 497
Page Count: 5
DOI: 10.2174/1570178611666140401222305
Advertisement

Related Journals




Webmaster Contact: urooj@benthamscience.org Copyright © 2014 Bentham Science