A new series of polysubstituted quinazoline derivatives has been furnished as a product of N-acylation, O-acylation and/or O-alkylation of the corresponding 2-methylquinazolinones; based on using the principles of lactam-lactim dynamic equilibrium phenomena and the role of solvent polarity in shifting such equilibrium. The reaction of the prepared polysubstituted quinazolines with different nitrogen, carbon, and sulphur nucleophiles has produced derivatives of 4-heteroaryl-quinazoline derivatives and interesting moieties such as oxadiazoles, triazoles, fused triazolo-thiadiazole, thiazole, furyl, and pyrazole were introduced at the 4-position of the quinazoline skeleton. Some of the synthesized compounds are tested for its antimicrobial activity.
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