Mohamed Abd, El Zein, E. A. A. El-Rahim
Oct 1, 2011
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Journal
Indian journal of applied research
Abstract
Substituted) amino-2-thioxoimidazolidinones (3a, b) were prepared via condensation of 1-substitued thio- semicarbazones (2a, b) with ethyl chloroacetate in presence of fused sodium acetate. Reaction of (3a,b) with acetic anhydride, ethyl acetate in presence of sodium metal in Xylene and aromatic aldehydes in presence of piperidine yielded the corresponding 1-acetyl-3-(substituted)amino-2-thioxoimidazolidinones(4a,b),5-acetyl-3-(substituted)amino- 2-thioxoimidazolidinones (5a,b) and 5-arylidene-3-(substituted) amino-2-thioxoimidazolidinones (6a,b). Reaction of (4a,b) with aromatic aldehydes in presence of piperidine and/or acetylation of (6a,b) by acetic anhydride yielded 1-acetyl-5- arylidene-3-(substituted) amino-2-thioxoimidazolidinones (7a,b). Bromination of (3a,b) with bromine gave the correspond- ing 5-bromo-3-(substituted)amino-2-thioxoimidazolidin-2-one (8a,b). Some of the synthesized compounds also exhibited antimicrobial activities. . Subsequently, we made a drastic change of the parent thiophene cyanoguandine core. We propose to install abridge connecting the two amino nitro- gens and thus, forming a cyclic structure containing 3-((thio- phene-2-yl)ethylidene) amino-2-thioxoimidazolidin-2-one moiety. This paper now reports the synthesis of trisubstituted thioxoimidazolidinones from 2-acetyl-5-methylthiophene and 2-acetyl-5-aminothiophene as key starting materials. The chemical analysis of trisubstituted thioxoimidazolidinones was described and their biological activity was evaluated. 2- Results and Discussion. The synthetic pathways leading to the new trisubstituted thi- oxoimidazolidinones are illustrated in Scheme 1. Treatment 6 of 2-acetyl-5-methylthiophene (1a) and 2-acetyl-5-aminothio- phene (1b) with thiosemicarbazide in methanol under reflux yielded the corresponding 2-(1-(5-methylthiophen-2-yl) ethylidene) hydrazinecarbothioamide (2a) and 2-(1-(5-ami- nothiophen-2-yl)ethylidene)hydrazinecarbothioamide (2b), respectively. The reaction of (2a, b) with ethyl chloroacetate in presence of fused sodium acetate in methanol under re- flux, gave the corresponding 3-(1-(5-methylthiophen-2-yl) ethylidene)amino-2-thioxoimidazolidin-4-one (3a) and 3-(1-(5-aminothiophen-2-yl)ethylidene)amino-2-thioxoimi- dazolidin-4-one (3b). Acetylation of compounds 3a and 3b with acetic anhydride under reflux led to the formation of 1-acetyl-3-(substituted)amino-2-thioxoimidazolidinones (4a, b). Acetylation 7 of compounds 3a and 3b with ethyl acetate in presence of sodium metal in xylene under reflux resulted in the formation of 5-acetyl-3-(substituted)amino-2-thioxo- imidazolidinones (5a, b). Condensation 8 of compounds 3a