Stereoselective synthesis and X-ray structure determination of novel 1,2-dihydroquinolinehydrazonopropanoate derivatives

Abstract

A novel series of 1,2-dihydroquinolinhydrazonopropanoate have been synthesized via a convenient aza-Michael addition reaction between hydrazinylquinolinones and ethyl propiolate in ethanol under refluxing temperature. The structures for all obtained products were confirmed with FTIR, NMR spectrums, as well as mass spectrometry. In addition, the monoclinic structure for compounds 8a, 8c, and 8d was also confirmed via X-ray crystallography analyses. The E-configuration for the obtained products was confirmed form the X-ray analysis. On the other hand, the crystal packing shows that the intermolecular and hydrogen bonds between atoms are parallel to the bc plan.

Keywords

• Aza-michael addition
• Hydrazono-hydrazides
• Stereoselective synthesis
• 4-Hydrazinyl-quinolin-2(1H)-Ones
• Ethyl propiolate
• 1,2-Dihydroquinolin-4-yl(hydrazono)propanoate and X-ray crystallography