Use of Ethyl p-(4-hydroxyphenyl)-α-cyanoacrylate in The Synthesis of Carbazone, Thiazole and Imidazolidin-2-thione Derivatives

摘要

CONDENSATION of ethyl p-(4-hydroxyphenyl)-α-cyanoacrylate with thiosemicarbazide gave the 4-hydroxybenzaldehyde thiosemicarbazone (3). Treatment of 3 with acetic anhydride, 4-substituted phenacyl bromide and ethyl chloroacetate yielded the corresponding N-acetyl derivative (4), thiazol derivative (5) and 3-substituted 4-oxo-imidazolidin-2-thione (6). Compound 6 reacted with benzyl chloride, methyl acrylate, phenyl- diazonium chloride and hydrazine hydrate to give 1-substituted imidazo-lidine-2-thione derivatives (7,8,9) and 1,2-bis (4-hydroxy-benzal-dehyde)-hydrazone (10). Treatment of 6 with acetic anhydride and 4-hydroxybenzaldehyde afforded the corresponding N-acetyl derivatives (11) and 5-substitued-imidazolidin-2-thione (12). The mass spectral fragmentation patterns of some compounds are described.