Synthesis and reactions of 2-cyano-2-(5-oxo-3-phenyl-thiazolidin-2-ylidene)-acetamides

Abstract

The base promoted nucleophilic addition of cyanoacetamide derivatives 2a,b to equimolar amount of phenyl isothiocyanate in DMF containing potassium hydroxide afforded the corresponding potassium sulfide salts 3a,b which were not isolated but which underwent heterocyclisation upon treatment with chloroacetyl chloride to give the corresponding 2-cyano-2-(5-oxo-3-phenylthiazolidin-2-ylidene)-acetamide derivatives 4a,b. The reactions of 4a,b with aryl diazonium salts, bromine and aromatic aldehydes were studied in order to obtain compounds 5–11.

New Thiazolidinones, Thiazolines and Thiopyrimidines from 3,5-Diphenylcyclohex-2-enone

“…The diversity of biological and physiological activities of organic sulfur heterocycles may be attributed to the presence of the NCS fragment, which is characteristicof thiazoles, thiazolines, and thiazolidines [27]. In view of the above findings and as an extension of our studies [28][29][30][31][32][33][34] aiming to the synthesis of different thiazoles, thiazolodinones and thiazolines, of expected pharmaceutical interest, we report here the reactivity of potassium N' -3,5diphenylcyclohex-2-enylidene-N-phenylcarbamoyl hydrazonothionate 4 toward different α-halogenated compounds.…”

Synthesis of Thiazolinone, Aminopyrazole, Pyrazolopyrimidine, and Pyrazolotriazine Derivatives Starting from 1‐Naphthyl‐2‐Cyanoacetamide

“…Now, we have extended our synthetic program to the synthesis of otherwise inaccessible heterocyclic ring systems utilizing 1-naphthyl-2-cyanoacetamide (1) and PhNCS as keys starting materials. It is known that a great variety of reactants bearing the N-C-S fragment undergo cyclization on reaction with α-halocarbonyl compounds to afford thiazole, 2,3-dihydro-thiazole and thiazolidines moieties [23] which have been shown to exhibit local antitumor and antioxidant [24], antimicrobial [25], and antitumor activity [26]. Here, we describe a generally applicable extension of this synthetic approach; the base prompted reaction of the acidic methylene compound (1) with phenyl isothiocyanate in dry dimethylformamide at room temperature yields the non-isolable intermediate (3).…”

Synthesis, Characterization and Biological Evaluation of Some Benzothiazole Derivatives as Potential Antimicrobial Agent.

“…In addition, a large number of thiophene derivatives have found to exhibit pharmacological activity [32][33][34] . Furthermore, diverse chemotherapeutic activities have ascribed to pyrazoles as antimicrobial [35][36] , antiparasitic 37 , antivirial 38 , and antineoplastic agents [39][40][41][42] . A detail literature survey indicates that benzothiazole ring system have a unique position in the designing and synthesis of novel biological active agents with remarkable analgesic and anti-inflammatory activities.The preliminary study of the structure-activity relationship reveals that electronic factors in benzothiazole ring has a great effect on a antimicrobial activity of these compounds.…”