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.

引用

页码：9404 / 9407

页数：4

共 49 条

[1] A New Approach for the Synthesis of Bioactive Heteroaryl Thiazolidine-2,4-diones
Ibrahim, Magdy Ahmed
Abdel-Hamed, Mohamed Abdel-Megid
El-Gohary, Naser Mohamed
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2011, 22 (06) : 1130 - U184
[2] 5-aryl thiazolidine-2,4-diones as selective PPAR-γ agonists
Koyama, H
Boueres, JK
Han, W
Metzger, EJ
Bergman, JP
Gratale, DF
Miller, DJ
Tolman, RL
MacNaul, KL
Berger, JP
Doebber, TW
Leung, K
Moller, DE
Heck, JV
Sahoo, SP
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (10) : 1801 - 1804
[3] Synthesis of 5-arylidene-3-(4′-bromobenzyl)thiazolidine-2,4-diones
Popov-Pergal, K
Pergal, M
Csanádi, J
Djokovic, D
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2005, (12): : 1854 - 1858
[4] Synthesis of 5-arylidene-3-(4′-bromobenzyl)thiazolidine-2,4-diones
Popov-Pergal K.
Pergal M.
Csanadi J.
Djokovic D.
Chemistry of Heterocyclic Compounds, 2005, 41 (12) : 1529 - 1533
[5] A simple approach to the synthesis of 3-substituted rhodanines and thiazolidine-2,4-diones
Aryanasab, F.
Shokri, A.
Saidi, M. R.
SCIENTIA IRANICA, 2013, 20 (06) : 1833 - 1838
[6] Anticancer activity of novel hybrid molecules containing 5-benzylidene thiazolidine-2,4-dione
Romagnoli, Romeo
Baraldi, Pier Giovanni
Salvador, Maria Kimatrai
Camacho, M. Encarnacion
Balzarini, Jan
Bermejo, Jaime
Estevez, Francisco
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 63 : 544 - 557
[7] Synthesis and Antiproliferative Evaluation of 2′-Arenesulfonyloxy-5-benzylidene-thiazolidine-2,4-diones
Chen, Emily M.
Lu, Pei-Jung
Shaw, Arthur Y.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (04) : 792 - 798
[8] 5-aryl thiazolidine-2,4-diones:: Discovery of PPAR dual α/γ agonists as antidiabetic agents
Desai, RC
Han, W
Metzger, EJ
Bergman, JP
Gratale, DF
MacNaul, KL
Berger, JP
Doebber, TW
Leung, K
Moller, DE
Heck, JV
Sahoo, SP
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (16) : 2795 - 2798
[9] SYNTHESIS AND PHARMACOLOGICAL EVALUATION OF SOME 3-PHENACYL-5-BENZYLIDENE-THIAZOLIDINE-2,4-DIONES
DELIMA, JG
PERRISSIN, M
CHANTEGREL, J
LUUDUC, C
ROUSSEAU, A
NARCISSE, G
ARZNEIMITTEL-FORSCHUNG/DRUG RESEARCH, 1994, 44-2 (07): : 831 - 834
[10] Structural and conformational studies of 5-(1H-pyrrol-2-ylmethylene)-substituted imidazolidine-2,4-diones and thiazolidine-2,4-diones
Dios, A
de la Puente, ML
Rivera-Sagredo, A
Espinosa, JF
CANADIAN JOURNAL OF CHEMISTRY, 2002, 80 (10) : 1302 - 1307

← 1 2 3 4 5 →