Synthesis and structure of new 5‐(arylidene)‐3‐(4‐methylbenzoyl)thiazolidine‐2,4‐diones

Abstract

in Wiley InterScience (www.interscience.wiley.com).The derivatives of 5-substituted-2,4-thiazolidinedione have a broad spectrum of biological activities. In this article, new 5-(arylidene)-3-(4-methylbenzoyl)thiayolidine-2,4-diones 3a-k, with arylidene groups such as 4-phenylbenzylidene 3a, 3,4-dimethoxybenzylidene 3b, 2-hydroxybenzylidene 3c, 4-ethoxybenzylidene 3d, 5-methyl-2-furfurylidene 3e, 4-dimethylaminobenzylidene 3f, 1-naphthylidene 3g, 3,4-methylenedioxybenzylidene 3h, 4-benzyloxybenzylidene 3i, benzylidene 3j, and 4-methoxybenzylidene 3k, were synthesized by direct acylation of alkali metal salts of 5-arylidene-2,4-thiazolidinediones with 4-methylbenzoylchloride. Their structures were confirmed by elemental analysis, IR, 1 H NMR and MS spectroscopy. In addition, crystal structure of the compound 3d was determined using single-crystal X-ray diffraction data.

Acyclic Twisted Amides

“…N , N -Diacyl activation represents one of the most effective methods for twisting amide bonds (Figure ). − In this class of amides, n N to π* CO conjugation is satisfied by delocalization onto two exocyclic carbonyl groups (cf. single CO, section ), which leads to enhanced geometric distortion dependent primarily on steric and to a lesser extent on electronic properties of the activating group (cf.…”

Antifungal Thiazolidines: Synthesis and Biological Evaluation of Mycosidine Congeners

“…Several articles have described 3-Benzoyl derivatives of 5-arylidene-thiazolidine-2,4-dione as potential herbicidal and antimicrobial agents. Their synthesis was based on 5-arylidene-thiazolidine-2,4-dione and the corresponding benzoyl chloride and it had a good yield in anhydrous acetone in the presence of K 2 CO 3 with heating [ 54 ] or in pyridine at 70 °C [ 55 ].…”

“…In addition, some derivatives of 7a , b were obtained that did not contain free hydroxyl groups in the phenyl ring. The reaction was carried out according to a published procedure using acetone with K 2 CO 3 under heating [ 54 ].…”

Tetrabutylammonium bromide and K2CO3: an eco-benign catalyst for the synthesis of 5-arylidene-1,3-thiazolidine- 2,4-diones via Knoevenagel condensation

“…Several bases such as piperidine, [17] piperidinium acetate, [18] sodium acetate [19] and ammonium acetate [20] were utilized to accelerate the Knoevenagel condensation. The catalytic function of urea and thiourea, [16] benzoic acid, [21] polyethylene glycol-300, [22] potash alum, [23] L-proline, [23] boric acid, [23] oxalic acid, [23] ionic liquids, [24] Bakers yeast, [25] Mg-doped Ce-Zr [26] and morpholine [27] were utilized in the improved syntheses.…”