Phenacyl Bromide: An Organic Intermediate for Synthesis of Five- and Six-Membered Bioactive Heterocycles

Abstract

An environmentally friendly, economic synthetic protocol was advanced for synthesis of biologically and pharmacologically vital five-and six-membered heterocycles containing nitrogen, sulphur and oxygen as heteroatom. A series of thiazole derivatives was prepared by the reaction of substituted phenacyl halides and phenyl thiourea in the presence of TiO 2 nanoparticles (NPs) as nanocatalyst in DCM. Similarly, another series of six-membered heterocyclic compounds were synthesized by the reaction of phenacyl halides with phenylenediamine, 2-aminophenol, 2-aminobenzenethiol to produce corresponding products (1,4-quinoxaline, benzoxazine, benzothiazine) under catalytic effect of TiO 2 nanocatalyst. Analytical and spectral (FTIR, 1 H and 13 C NMR and SEM) techniques were employed for the structural elucidation of the synthesized compounds.

Design, Synthesis, Anticancer Evaluation, and Molecular Docking Studies of Oxazole‐Incorporated Naphthyridine Derivatives

“…The ESIMS of 19 showed the (M+H) + ion peak at m/z 290 would confirmed the formation of product. In the last step, intermediate 19 was subjected to cyclization [31] with various types of phenacyl bromides ( 20 a – j ) in ethanol solvent while stirring under reflux for 12 hours which afforded the final derivatives 21 a – j . The 1 H‐NMR spectrum of compound 21 a , the signal resonate at δ 3.78 (s, 3H), 3.89 (s, 6H) would determine three methoxy protons attached to phenyl ring.…”