Using of Some 2(3H)-Furanone Derivatives as Building Block for Synthesis of Some Nitrogen Heterocycles of Anticipated Biological Activity

Abstract

Part I: The reactivity of a 2-chloroquinolinylfuranone derivative was investigated toward two nitrogen nucleophilic reagents namely, hydrazine hydrate and benzylamine. It was found that the regioselectivity of the reaction products was mainly dependent on the nature of nucleophiles, reaction conditions, and solvent used. Therefore, hydrazinolysis of the titled furanone derivative afforded the corresponding acid hydrazide and pyridazinone derivatives. Otherwise, benzylamine reacted with this furanone at different reaction aspects to provide N-benzylamide, N-benzylpyrrolone, and 2-benzylaminoquinolinyl-N-benzylpyrrolone derivatives. The chemical structures of all synthesized compounds were substantiated from their analytical as well as spectroscopic data. Based on the charge density calculations and computational chemical study which excluded the aza-Michael addition reaction and confirm the higher electron-deficiency of lactone carbonyl group than C2-quinoline position, it can be concluded that the C2-furanone becomes more susceptible to attack by the nucleophilic reagent (hydrazine hydrate and benzylamine). Part II: The acid hydrazide derivative 4, reported in Part I, was transformed into a variety of valuable N-heterocycles like pyridazinone, oxadiazole, triazolopyridazine and triazole derivatives. Some of the synthesized compounds were studied using DFT calculations and uploaded on chitosan nanoparticles to obtain different CS-heterocycles nanocomposites. They were characterized using TEM, XRD and IR techniques and exhibited a somewhat narrow size distribution with an average particle size of 19-50 nm. Part III: The insecticidal activity for some of the synthesized N-heterocycles and their nanocomposites obtained were evaluated against Mythimna separata and Nilaparvata lugens. After loading the N-heterocycles on chitosan nanoparticles, the insecticidal activity was enhanced.