Use of salicylaldehyde in the synthesis of 2-thioxoimidazolidinone and salicyladazine derivatives

Samar A. Abubshait

Abstract

5-arylazo-2- hydroxybenzaldehyde thiosemicarbazones (2a-c) and 2-[(5-arylazo-2-hydroxybenzylidene)-amino]- benzoic acids (3a-c) were prepared via condensation of 5- arylazo-2- hydroxybenzaldehyde (1) with thiosemicarbazide and 2-amino benzoic acid. 3-substituent- imidazolidinones (4a-c) were synthesized by the reaction of 2 with ethyl chloro acetate in presence of fused sodium acetate. Bezoylation and acetylation of 3- substituent- imidazolidinones (4a-c) with benzoyl chloride and acetic anhydride in presence or absence of fused sodium acetate led to the formation of bezoyl derivatives (7) and acetyl derivatives (5, 6). 5-aryl salicyladazines (8 a-c) were obtained by hydrazonlysis of 3, 5 and 6 with hydrazine hydrate. The electron impact mass spectra of both of the above some series of compounds have also recorded and their fragmentation pattern is discussed