A Novel PIFA/KOH Promoted Approach to Synthesize C2-arylacylated Benzothiazoles as Potential Drug Scaffolds

Abstract

To discover an efficient and convenient method to synthesize C2-arylacylated benzothiazoles as potential drug scaffolds, a novel [bis(trifluoroacetoxy)iodo]benzene(PIFA)/KOH synergistically promoted direct ring-opening C2-arylacylation reaction of 2H-benzothiazoles with aryl methyl ketones has been developed. Various substrates were tolerated under optimized conditions affording the C2-arylacylation products in 70–95% yields for 38 examples. A plausible mechanism was also proposed based on a series of controlled experiments.

Phenyliodine bis(trifluoroacetate) as a sustainable reagent: exploring its significance in organic synthesis

“…Sun et al 77 developed an efficient method using PIFA as a mediator to synthesize distinct C -2-arylacylated benzothiazoles 37 with yields ranging from 70% to 95%. These compounds show promise as potential therapeutic scaffolds and are obtained through a ring-opening reaction of 2 H -benzothiazoles 35 (Scheme 14).…”

Synthesis of Few New Carrier Polymers Derived from 2-hydrazinylbenzo[d]thiazole

“…16,17 Benzothiazole must get the attention of the medicinal chemists due to their wide variety of biological activities, including anti-inflammatory, vasodilators, antitumor, [18][19][20] anti-tubercular, antifungal, 21 antimicrobial, 22 anticancer, 23 antidiabetic, 24 anti-convulsant, 25 antibacterial and antiviral activities. 26 Maleimide is a chemical compound with the formula H 2 C 2 (CO) 2 NH, maleimides can be defined as an important kind of heterocyclic compounds that exist in natural products 27 and find applications in organic as well as medicinal chemistry. 28 Maleimides have considerable significance in pharmaceutical products with biological particular, e.g., antibacterial, anticancer, anti-tumor, tuberculostatic activity, antimicrobial, anti-viral and anti-genic activities.…”

New Synthetic Methodology for Drug-like Molecules

“…iodine chemistry for the C2-arylacetylation of benzothiazoles via an unusual demethylative reaction of methylaryl ketones [21]. Benzothiazoles are well established as of the most common ring systems in FDA-approved drugs [22], and 2-arylacyl examples encompass a broad range of bioactivities [23][24][25][26][27][28].…”