Iodine- and TBHP-Promoted Acylation of Benzothiazoles under Metal-Free Conditions

Abstract

A simple protocol for the synthesis of 2-acylbenzothiazoles using aryl ketones and benzothiazoles in the presence of I2 and TBHP is described. Acylation of the benzothiazoles is achieved through a sequence involving oxidation of the aryl ketone to an aryl glyoxal, ring-opening of the benzothiazole followed by condensation of the amino group with the aryl glyoxal, cyclization and oxidation. The method avoids the use of metals and toxic solvents. In addition, this protocol has the advantage of broad scope and provides good to excellent product yields.

Strategies towards the Synthesis of 2‐Ketoaryl Azole Derivatives using C‐H Functionalization Approach and 1,2‐Bis‐Nucleophile Precursors

“…The developed route avoids the use of metals and toxic solvents (Scheme 17). [41] The proposed transformation begins by the conversion of acetophenone 44 a into phenylglyoxal I using I 2 in DMSO as solvent via Kornblum oxidation process. [42] In this process, the byproduct HI can be oxidized using DMSO or TBHP to reproduce I 2 .…”