Reactions with 1-Phenyl-4-thiohydantoin. Preparation of 5-Arylazo-1-phenyl-4-thiohydantoin, their Reactions towards Alkylating Agents and Mannich Reaction

Abstract

l-Phenyl-4-thiohydantoin, Alkylating Agents, Amines, Mannich Reaction l-Phenyl-4-thiohydantoin reacted with aryldiazonium salts to give the corresponding 5-arylazo-l-phenyl-4-thiohydantoin (la-f). On alkylation of la,b,f with different alkyl halides, the corresponding 4-alkylmercapto derivatives (2 a-f) were obtained. 2 a was hydrolysed with a mixture of ethanol-hydrochloric acid to give 5-phenylazo-l-phenylhydantoin (3). Treatment of 2a,d with amines gave the products 4a-h. 4a when refluxed with a mixture of acetic-hydrochloric acid, the product 3 was obtained. la,b reacted with formaldehyde and appropriate amine to give the corresponding Mannich bases 5 a-k. Also l-phenyl-4-thiohydantoin when exposed to the Mannich reaction, 6 a-e were obtained. 6 a when treated with benzenediazonium chloride, the colour substance 5 a was separated.

Synthesis of New Azocompounds and Fused Pyrazolo[5,1-c][1,2,4]triazines Using Heterocyclic Components

“…In addition, the synthetic possibilities of 1,3‐thiazolidine‐2,4‐dione and 2‐thioxo‐1,3‐thiazolidin‐4‐one (rhodanin) as methylene active components in reactions with diazonium salt were considered. The aforementioned heterocycles were found to be incorporated into natural subtracts and medicines . Therefore, the inclusion of these compounds in synthetic polyheterocyclic systems made it possible to model many potential drugs.…”

Facile Synthesis of 5-Arylidene Thiohydantoin by Sequential Sulfonylation/Desulfination Reaction

“…Therefore, there has been great demand for highly efficient synthetic methods for the introduction of arylidene carbon-carbon double bond at the 5-position of the hydantoin or thiohydantoin ring [1,2]. So far, several typical synthetic strategies of 5-arylidene derivatives of hydantoin and thiohydantoin have been reported, including a traditional base-catalyzed aldol condensation of hydantoin and thiohydantoin with substituted benzaldehydes [1,3,5,6,9], improved aldol condensation such as one-pot multicomponent reaction of substituted benzaldehydes, glycine and potassium thiocyanate [10], microwave-assisted condensation of thiohydantoin/hydantoin with substituted benzaldehyde Schiff bases [11], Wittig-Horner Reaction [12–14], and Mn-catalyzed reactions of terminal alkynes with isocyanates [15]. Herein, we report a new protocol via sequential sulfonylation/desulfination to construct the 5-arylidene thiohydantoin.…”