Synthesis, DFT, and eco-friendly insecticidal activity of some N-heterocycles derived from 4-((2-oxo-1,2-dihydroquinolin-3-yl)methylene)-2-phenyloxazol-5(4H)-one

Abstract

A new series of nitrogen heterocycles encompassing a quinoline scaffold such as imidazolone, benzimidazole, triazinone, triazole, and thiazole derivatives was synthesized utilizing the readily obtainable building block synthon, 4-((2-oxo-1,2-dihydroquinolin-3-yl)methylene)-2-phenyloxazol-5(4H)-one (3). It was interesting that the fused heterocycle, pyranoquinoline derivative 15 was successfully synthesized by different routes of reactions. The synthesized compounds were evaluated for their insecticidal activity and compounds 6, 17, and 20 were the most potent against both Mythimna separata and Nilaparvata lugens. The DFT study was performed for the most potent compounds.

Keywords: Benzimidazole; Insecticidal; Oxazolone; Quinolone; Triazinone.