Studies On The Structure Of Pharmacophore Skeletons Using Substituted Nitrostyrenes

Recently, based on nitroalkenes several multicomponent reactions have been reported for the synthesis of the heterocyclic compounds by condensation reactions employing nitroalkenes as a useful building block for the formation of carbon-carbon bond, which has been used as a powerful tool in synthesis and foreseeable applications of medicinal chemistry, chemical biology, materials science and pharmaceutical industry.In this thesis, we reported our efforts towards developing new, singly-operated multicomponent reactions for the direct synthesis of fully substituted β-aminoesters, polysubstituted naphthofuranamines, pyrrolocoumarins. The resulting biologically intriguing structures could have broad applications in related biomedical program structures.Part 1:Polysubstituted β-aminoesters were synthesized via one-pot reaction of substituted benzaldehydes, nitromethane and alkyl cyanoacetates in the presence of triethylamine. We synthesized twenty new products under optimizing the reaction conditions. All compounds were characterized by NMR, IR and LC-MS spectroscopy. The single crystal structures of four polysubstituted P-aminoesters were confirmed by X-ray diffraction method.Part 2:Polysubstituted naphthofuranamines were synthesized via one-pot reaction of naphthols,β-nitrostyrenes, substituted benzaldehydes and ammonium acetate in the presence of sodium hydroxide. We synthesized twenty-four new products under optimizing the reaction conditions. All compounds were characterized by NMR, IR and LC-MS spectroscopy. The single crystal structures of two polysubstituted naphthofuranamines were confirmed by X-ray diffraction method.Part 3:Polysubstituted pyrrole-coumarins were synthesized via one-pot reaction of β-nitrostyrenes, dimethyl acetylenedicarboxylate and amines in the presence of Lewis acid.We synthesized eighteen new products under optimizing the reaction conditions. All compounds were characterized by NMR, IR and LC-MS spectroscopy. The single crystal structures of one polysubstituted pyrrole-coumarins were confirmed by X-ray diffraction method.