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

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

Volume: 11 Issue: 7

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

Affiliation:

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

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.

Cite this article as:

A. Kaczor Agnieszka, Aletaska-Kozak Monika, Wrobel Tomasz and Matosiuk Dariusz, Synthesis, Experimental and Computational Spectroscopic Studies, and Formation Thermodynamics of Diethyl [[2-(1-Aryl-4,5-dihydro-1H-imidazol- 2-yl)hydrazinyl]methylene]propanedioates, Letters in Organic Chemistry 2014; 11 (7) . https://dx.doi.org/10.2174/1570178611666140401222305