Ahmed M. Sh. El-Shareif, Y. Ammar, M. El-Gaby
2003
Citations
0
Influential Citations
8
Citations
Journal
Afinidad
Abstract
Imidazolidinones 2a-c,3 and 5 were synthesized via the reaction of cyanothioformamides 1a,b with aromatic isocyanates, ally isothiocyanate and benzoyl isothiocyanate, respectively. Cyclization of 3 with o-phenylenediamine afforded the imidazo[4,5-b]quinoxaline 4, via elimination of HAS and NH 3 . Reduction of 2 with hydrogen sulfide in absolute ethanol /TEA, yielded the thiohydantoins 6a,b, with conversion of imino group to methylene group. Treatment of 6 with some electrophilic reagents such as aromatic aldehydes, triethylorthoformate and dimethylformamide-dimethylacetal (DMFDMA) furnished the novel imidazolidinones 7, 8 and 9, respectively. Thiopyrano[2,3-d]imidazoles 12a-c were obtained by refluxing of benzylidene malononitrile with 6 in ethanol containing catalytic amount of piperidine. Interaction of 6 with chloroacetic acid yielded the thieno[2,3-d]imidazole 15. Refluxing of 5 with o-phenylene-diamine and anthranilic acid furnished the imidazo[4,5-b]quinoxaline 19 and imidazo [3,4 -b] quinazoline 20, respectively.