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

Xiao-Tong Sun; Zhi-Gang Hu; Zhen Huang; Ling-Li Zhou; Jian-Quan Weng

doi:10.3390/molecules27030726

Molecules (Jan 2022)

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

Xiao-Tong Sun,
Zhi-Gang Hu,
Zhen Huang,
Ling-Li Zhou,
Jian-Quan Weng

Affiliations

Xiao-Tong Sun: College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China
Zhi-Gang Hu: College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China
Zhen Huang: College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China
Ling-Li Zhou: College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China
Jian-Quan Weng: College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China

DOI: https://doi.org/10.3390/molecules27030726
Journal volume & issue: Vol. 27, no. 3
p. 726

Abstract

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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.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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