Electrochemical reduction of 5-benzylidene thiazolidine-2,4-diones: a greener approach to the preparation of glitazone APIs

被引：2
|
作者：
de Castro, Pedro P. [1 ]
Martins, Guilherme M. [1 ]
Gomes, Ronewalber B. [1 ]
Simoso, Guilherme B. [1 ]
Amarante, Giovanni W. [2 ]
Brocksom, Timothy J. [1 ]
de Oliveira, Kleber T. [1 ]
机构：
[1] Univ Fed Sao Carlos, Dept Chem, BR-13565905 Sao Carlos, SP, Brazil
[2] Univ Fed Juiz de Fora, Dept Chem, Campus Martelos, BR-36036900 Juiz De Fora, MG, Brazil
来源：
CHEMICAL COMMUNICATIONS | 2023年 / 59卷 / 61期
基金：
巴西圣保罗研究基金会;
关键词：
HYDROGENATION;
D O I：
10.1039/d3cc02363j
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A transition-metal free methodology for the chemoselective reduction of benzylidene thiazolidine-2,4-diones and similar heterocycles is described, allowing the preparation of a broad scope of the corresponding reduced derivatives in up to 90% yield. The protocol has a simple and safe experimental setup, in which water was employed as the hydrogen source. To further demonstrate the synthetic utility of this transformation, the antidiabetic API Pioglitazone was prepared in 81% yield. To the best of our knowledge, this is the first hydride and transition-metal free protocol for the synthesis of Pioglitazone, highlighting its potential utility as a greener alternative in both academic and industrial synthesis.
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页码：9404 / 9407
页数：4
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