Thesis (M.Sc.) - Cairo University - Faculty of Science - Department of Organic Chemistry

The original work of this thesis includes: A series of arylidene derivatives 4a-l, 2-imino-chromene derivatives 6a-e and aryl hydrazones derivates 8a-d were synthesized via the reaction of 2-cyano-N-(1,3-dihydroxy-2-(hydroxylmethyl) propan-2-yl) acetamide 2 with aldehydes and aryldiazonium salts. Refluxing cyanoacetamide derivative 2 with phenyl isothiocyanate and elemental sulfur afforded 4-amino-N-(1,3-dihydroxy-2-(hydroxymethyl) propan-2-yl)-3-phenyl-2- thioxo-2, 3-5-carboxamide 9. Also, reaction of 2 with cyclopentanone or cyclohexanone and elemental sulfur gave the corresponding aminothiophene derivatives 10. Treatment of cyanoacetamide derivative 2 with pentane-2,4-dione provided aminothiophene derivative 11. Condensation of enaminonitrile derivative 12 with 4-(phenyldiazenyl)-1H- pyrazole-3, 5-diamine derivatives 13a-e furnished pyrazolo [1,5-a] pyrimidine derivatives 14a-e. Refluxing of 12 with cyanoguanidine and guanidine nitrate produced 2,4-diimino-1,2,3,4-tetrahydropyrimidine-5-carboxamides 15 and 16 respectivly. Also, grinding enaminonitrile 12 with hydrazine hydrate provided 3-amino-N-(1,3-dihydroxy-2-(hydroxymethyl) propan-2-yl)-1H-pyrazole-4-carboxamide 17. The newly synthesized compounds were proved by elemental and spectral data. All plausible mechanisms for their formation were discussed. Some of the selected products were tested and evaluated as antimicrobial agents

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