A one-pot electrochemical synthesis of 2-aminothiazoles from active methylene ketones and thioureas mediated by NH₄I

Abstract

The electrochemical preparation of 2-aminothiazoles has been achieved by the reaction of active methylene ketones with thioureas assisted by ᴅʟ-alanine using NH4I as a redox mediator. The electrochemical protocol proceeds in an undivided cell equipped with graphite plate electrodes under constant current conditions. Various active methylene ketones, including β-keto ester, β-keto amide, β-keto nitrile, β-keto sulfone and 1,3-diketones, can be converted to the corresponding 2-aminothiazoles. Mechanistically, the in situ generated α-iodoketone was proposed to be the key active species.

Visible-light-induced C–S bond formation in the synthesis of 2,4-disubstituted thiazoles through cascade difunctionalization of acetophenone: a greener approach

“…9,10 Thiazole is a precious and synthetically important framework known for its diverse biological activities. [11][12][13] The synthesis of phenyl thiazole compounds has garnered substantial interest in therapeutic science due to their potential pharmacological importance. These compounds have demonstrated potent and noteworthy biological effects 14,15 similar to various existing drugs with well-established uses.…”

Design of a new method for one-pot synthesis of 2-amino thiazoles using trichloroisocyanuric acid in the presence of a novel multi-functional and magnetically catalytic nanosystem: Ca/4-MePy-IL@ZY-Fe3O4

“…In this regard, in situ α-halogenation strategies using various halogenating reagents including Br 2 , 7 I 2 , 8–11 NBS, 12,13 1,3-dichloro 5,5-dimethylhydantoin, 14 etc. 15,16 have been developed. Despite the benefits of the earlier techniques, there is still a need to enhance the preparation of 2-aminothiazoles using novel techniques and catalysts since the class of these compounds has a large impact on synthetic chemistry and medicines.…”

An electrochemical-enabled cascaded cyclization of enaminones with potassium thiocyanate and alcohols to access 2-alkoxythiazoles

“…Until now, there have been few reports on the application of electrochemical synthesis strategies in the construction of thiazole compounds. 16 However, all of these methods are limited to the synthesis of 2-aminothiazole compounds, while 2-alkoxythiazoles remain incomprehensible. Considering the importance of 2-alkoxythiazoles frameworks, and together with our growing interest in organic electrochemistry and C–H bond functionalization and annulation, herein we wish to report an efficient electrochemical strategy for the synthesis of 2-alkoxyethiazole derivatives via a three-component cascade reaction in one pot (Scheme 1d).…”