"The reactions of 3-anilinoenones with active methylene nitrile either in acid or base media were investigated. Reasonable mechanisms to account for the formation of the nicotinonitrile, ethyl nicotinate, nicotinic acid and dienamide derivatives were suggested. A one-pot multicomponent reactions (MCRs) of enaminone, aniline and either malononitrile or ethyl cyanoacetate in acid or base media afforded 1,3,5-triacycl benzene derivative. Treatment of N-phenyl cinnamamide with malononitrile in refluxing sodium ethoxide lead to tetrahydropyridine derivative. The structures of the synthesized compounds were elucidated by elemental analyses, X-ray and a variety of spectroscopic methods, including proton and carbon nuclear magnetic resonance spectroscopy ( 1 H-NMR and 13 C-NMR), correlation spectroscopy (COSY), heteronuclear single quantum coherence spectroscopy (HSQC), and mass spectrometry (MS).
The chemistry of enaminones is recognized as a significant field of study because enaminones serve as both starting materials for the synthesis of various heterocyclic compounds that have potential agrochemical use and as intermediates in dye and pharmaceutical industries. Due to their biological activities and pharmacological properties, pyridines and pyridones represent an important class of compounds that have been developed using functionally substituted enaminones. The structures of the synthesized compounds were elucidated by elemental analyses, 1 H-NMR; 13 C-NMR spectra; COSY; HSQC; MS and X-ray investigations.
Last date updated on July, 2014