Use of ethyl beta-[4-hydroxyphenyl]-alpha-cyanoacrylate in the synthesis of carbazone, thiazol and imidazolidin-2-thione derivatives

ABSTRACT

Condensation of ethyl beta-[4-hydroxyphenyl]-alpha-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