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

• Published in: Zeitschrift für Naturforschung. B, A journal of chemical sciences Vol. 31; no. 6; pp. 865 - 869
• Main Authors: Shalaby, A. F. A., Daboun, H. A., Boghdadi, S. S. M.
• Format: Journal Article
• Language: English
• Published: Verlag der Zeitschrift für Naturforschung 01.06.1976
• ISSN: 0932-0776; 1865-7117
• DOI: 10.1515/znb-1976-0628

1-Phenyl-4-thiohydantoin reacted with aryldiazonium salts to give the corresponding 5-arylazo-1-phenyl-4-thiohydantoin (1 a-f). On alkylation of 1 a, b,f with different alkyl halides, the corresponding 4-alkylmercapto derivatives (2a-f) were obtained. 2 a was hydrolysed with a mixture of ethanol-hydrochloric acid to give 5-phenylazo-1-phenyl-hydantoin (3). Treatment of 2 a, d with amines gave the products 4a—h. 4 a when refluxed with a mixture of acetic-hydrochloric acid, the product 3 was obtained, 1a, b reacted with formaldehyde and appropriate amine to give the corresponding Mannich bases 5 a-k. Also 1-phenyl-4-thiohydantoin when exposed to the Mannich reaction, 6a-e were obtained, 6 a when treated with benzenediazonium chloride, the colour substance 5 a was separated.