Solvent-Free Synthesis of 5-Benzylidene-2-Thioxothiazolidin-4-Ones and Thiazolidine-2,4-Diones Catalysed by Glycine under Microwave Irradiation

Abstract

A novel and clean synthesis of 5-benzylidene-2-thioxothiazolidin-4-ones and thiazolidine-2,4-diones has been achieved in good yields by condensation of aromatic aldehydes with rhodanine or thiazolidine-2,4-dione under microwave irradiation using glycine as the catalyst.

Evaluation of Reaction Between 2,4-Thiazolidinedione and P-Methoxybenzaldehyde in Microreactors for Production of Drugs for Treatment of Diabetes Mellitus Type 2

“…Considering the good results from melting point, the infrared (IR) analysis was carried out to determine the organic functions of the compound. In accordance with Yang and Yang (2011) the following infrared stretchings (KBr) were expected: 3137 (N-H), 1687 (C=O), 1585 (C=O). In the synthesized compound analysis (Figure S11), the IR stretching found were: 2360 (N-H), 1687 (C=O), 1579 (C=O), demonstrating its similarity with literature data.…”

Ultrasound-assisted synthesis of 2,4-thiazolidinedione and rhodanine derivatives catalyzed by task-specific ionic liquid: [TMG][Lac]

“…To achieve this end, several production protocols are reported employing several catalysts used such as amines [11], amine derivatives [12], amines salts [13], baker's yeast [14], sodium acetate [15-17], glycine [18,19], KF-Al 2 O 3 [20], and ionic liquids [21-25]. Several of these existing protocols for achieving this step have drawbacks like having long reaction times and low yields and leaving toxic residues on aqueous work-up; amine use is also now found to be carcinogenic.…”

A Rapid and Green Procedure for the Synthesis of 5- Arylidene Rhodanine Derivatives

“…The preparation of 5-arylidene rhodanine derivatives can be carried out by condensation of aromatic aldehydes and rhodanine in the presence of various catalysts such as glycine [4], ammonium acetate [5][6], 2,2,6,6-tetramethyl piperidine [7][8], NaOAc/HOAc [2,9-10], 1-butyl-3-methyl imidazolium hydroxide [11][12], NH 4 Cl/NH 4 OH [13], ethylenediammonium diacetate [14], K 2 CO 3 /[bmim]BF 4 /H 2 O [15], piperidine [1,[16][17], piperidine/AcOH [18][19][20]. Unfortunately, many of these methods suffer from one or other limitations such as low product yields, tedious work-up procedures, relatively long reaction time, use of organic solvent, use of special apparatus, use of expensive catalyst and difficulty in recovery and reusability of the catalyst.…”