Sanaa Osman Abd Allah

Arylazoisoxazolinthiones: Preparation and Reactions of 4-Arylazo-3-methyl-2-isoxazolin-5-thiones

Abstract The arylazo derivatives (2) of 3-methyl-2-isoxazolin-5-thione were prepared. Alkylation of 2 with alkyl halides results in the formation of the S-alkyl derivatives (5). The S-acetate esters undergo thermal isomerisation to the corresponding 1,2,3-triazole derivatives (6). The thiones 2 condense with hydrazines and primary amines to afford the corresponding 5-hydrazones and 5-imines (8) and (10), respectively. Treatment of 2 with hydrazine hydrate and Phenylhydrazine in boiling alcohol effects ring cleavage with the formation of 9.

Reactions with 5-Arylmethylene-2-phenylhydrazono-4-thiazolidinones A Novel Synthesis of Thiazolo[2,3-c]triazine Derivatives

The 5-arylmethylene derivatives of 2-phenylhydrazono-4-thiazolidinone (1) reacted with phenacyl bromide and with ethyl bromoacetate to yield the thiazolo[2,3-c]triazine derivatives (3) and (4). The reaction of 1 with carbon disulphide in alkaline solution afforded the bis(N1- 2-phenylhydrazono-4-thiazolidinone)thiocarbonyl derivatives (6). Cyanoethylation of 1 afforded the N1-β-cyanoethylphenylhydrazono derivatives (7).