A Convenient Synthesis of N-Substituted 2-Thioxo-1,3-thiazolidin-4-ones

Abstract

A convenient method was developed for the synthesis of N-substituted rhodanines based on the reaction of amines, hydrazides, or acid thiohydrazides with trithiocarbonyl diglycolic acid in the presence of dicyclohexylcarbodiimide or 1,1¢-carbonyldiimidazole.

Synthesis of fused heterocyclic compounds from arylidenerhodanines under microwave irradiation

“…General procedure 7 A solution of trithiocarbonyldiglycolic acid (0.24 g, 1 mmol) and carbonyldiimidazole (0.32 g, 2 mmol) in tetrahydrofuran (10 mL) was stirred at room temperature for 1.5 h. The appropriate amine or hydrazide (1 mmol) was added, and the reaction mixture was refluxed for 4 h. Then 2 М hydrochloric acid (30 mL) was added, and the mixture was extracted with ethyl acetate (4×15 mL). The organic phases were combined, dried with MgSO 4 , and concentrated.…”

“…The reactions of 5-arylidene-1,3-thiazolidine-2,4-dithiones with dimethyl acetylenedicarboxylate (DMAD), maleic anhydride, maleimide, and acrylonitrile in acetic acid at room temperature have been reported to yield thiopyrano [2,3-d]thiazolidine-2-thiones. presence of carbonyldiimidazole affords N-substituted rhodanines 1, 7 which upon reaction with arylaldehydes form the corresponding arylidene derivatives 2 (Scheme 1). 7 PhNHC(S)C(O)NH1b 7 4-ClC 6 H 4 NHC(S)C(O)NH1c 7 …”

“…presence of carbonyldiimidazole affords N-substituted rhodanines 1, 7 which upon reaction with arylaldehydes form the corresponding arylidene derivatives 2 (Scheme 1). 7 PhNHC(S)C(O)NH1b 7 4-ClC 6 H 4 NHC(S)C(O)NH1c 7 …”

An efficient microwave assisted synthesis of novel class of Rhodanine derivatives as potential HIV-1 and JSP-1 inhibitors

“…The spectra of compounds 7a-q display characteristic band s and C=S group (intense bands at 1628-1610 cm −1 ). The 3-phenyl due to stretching vibrations of two C=O groups (1720 cm −1 range -2-thioxothiazolidin-4-ones ( 3a-h ) derivatives were prepared by the literature 9 procedure by refluxing equimolar amounts of suitably substituted aromatic amines ( 1a-e ) and di-(carboxymethyl)-trithiocarbonyl ( 2 ). The aldehydes 6a-d were synthesized by treating corresponding acid chlorides with HSnBu 3 .…”

Synthesis of 2-thioxo-1,3-thiazolidin-4-one derivatives

“…3 The characteristics of the primarily synthesized compounds are given in Tables 1 and 2 , J = 9.0); 7.85 (d, 1 Н, СН arom , J = 3.6); 8.00 (s, 1 Н, СН aliph ); 11.10 (s, 1 Н, NH) 2g…”