Reactivity of 5-phenyl-3-[(2-chloroquinolin-3-yl)methylene] furan-2(3H)-one towards hydrazine and benzylamine: A comparative study

Abstract

The reactivity of a 2-chloroquinolinylfuranone derivative 3 was investigated against two nitrogen nucleophilic reagents namely, hydrazine 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 3 afforded the corresponding acid hydrazide and pyridazinone derivatives depending on the reaction conditions. Otherwise, benzylamine reacted with 3 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 and benzylamine.

Graphical Abstract

Keywords:

• 2-Chloroquinolin-3-carbaldehyde
• computational chemistry
• 2(3H)-furanone
• reactivity
• ring transformation

Disclosure statement

No potential conflict of interest was reported by the author(s).