Quinazolin-4(3H)-ones: A Tangible Synthesis Protocol via an Oxidative Olefin Bond Cleavage Using Metal-Catalyst Free Conditions

Abstract

An efficient and selective oxidative procedure for the synthesis of quinazolinones from readily available o-aminobenzamides and styrenes was developed. A number of potentially pharmacologically relevant quinazolinones were prepared using metal- and catalyst-free conditions. The synthesis procedure highlights the sustainable operation, low-priced, free from perilous materials, green solvent and environmental affability. The synthesized products were isolated in moderate to excellent yields.

Nanocatalyzed Synthetic Approach for the Quinazolinone and Quinazoline Derivatives: A Review (2015 – Present)

“…Di-tertiary-butyl peroxide (DTBP) and p-toluene sulfonic acid (p-TsOH) were used by Sharif to create 2-phenylquinazolin-4(3H)-one by reacting 2-aminobenzamide with styrene 15 .…”

Recent Advances on Quinazoline Derivatives: A Potential Bioactive Scaffold in Medicinal Chemistry

“…(v) Synthesis of quinazoline-2,4(1H,3H)-dione: Anthranilic acid and potassium cyanate reacted to get o-ureidobenzoic acid followed by cyclization by heating with acid or base to result in respective quinazoline-2,4(1H,3H)-dione (Figure 6) [10]. (vi) Synthesis of 2-phenylquinazolin-4(3H)-one: 2-aminobenzamide reacted with styrene using Di-tertiary-butyl peroxide (DTBP) and p-Toluene sulfonic acid (p-TsOH) to get 2-phenylquinazolin-4(3H)-one (Figure 7) [11].…”

[DDQM][HSO4]/TBHP as a Multifunctional Catalyst for the Metal Free Tandem Oxidative Synthesis of 2-Phenylquinazolin-4(3H)-ones

“…2-Phenylquinazolin-4­(3 H )-ones are prime nitrogen-containing heterocycles used as anticancer agents, anti-inflammatory agents, antibacterial agents, , etc. In an effort to expand the range of synthetic methods for the preparation of 2-phenylquinazolin-4­(3 H )-ones, numerous protocols in which either carboxylic acid and 2-amino benzamide or anthranilamide and aromatic aldehydes were used as starting precursors have been developed. In recent times, the oxidative synthesis of quinazolinones is in great demand, but the synthetic protocols require transition metal catalysts, longer reaction times, and harsh conditions.…”