Synthesis, reactions and biological evaluation of some chalcones and schiff bases incorporating heterocyclic compounds / Shorouk Sayed Mukhtar Tmam ; Supervised Hamdi M. Hassaneen , Taghrid Shoukry Mohamed Hafez , Fatma Mohamed Saleh Ali

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

The present dissertation includes two parts. The first part concerned with utility of 4-(piperidin-1- yl)benzaldehyde 5a and 4-morpholinobenzaldehyde 5b in the synthesis of chalcones 6, 12A, 12B, 12C and 17 via reaction with triazoloisoquinolines 4A-E, and pyrazole derivatives 11A-C and 16A-C. Ferrocene-2-carboxaldehyde was reacted with 11C and 16 to give chalcones 13 and 18. Also, chalcone 20 was prepared via reaction of 16C with benzaldehyde. The latter chalcone 20 was reacted with nitrilimines 21D-G to give the pyrazoline cycloaddition products 22D-G. Oxidation of the latter pyrazoline cycloadducts 22D-G with chloranil in boiling xylene afforded the corresponding pyrazoles 23D-G. Also, chalcones 6(A-C) and 17Ca were reacted with hydrazine hydrate in boiling ethanol to give 7(A-C) and 19, respectively. The second part of the dissertation concerned with synthesis of Schiff bases. Thus, 4- antipyrinecarboxaldehyde 5a, 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde 5b, 4-(piperidin- 1-yl)benzaldehyde 8, thiophene-2-carbaldehyde 9, nicotinaldehyde 10 and ferrocene-2-carboxaldehyde 14 were reacted with 5-amino-N-aryl-3-(phenyl amino)-1H-pyrazole-4-carboximides 4a-c to yield the corresponding Schiff bases 6a-c, 7a-c, 11a-c, 12a-c, 13a-c and 15a-c. The structures of new compounds were elucidated on the basis of spectral data (¹H NMR, ¹³C NMR, IR, and MS) and elemental analysis. Antimicrobial activity for some of the new prepared compounds were studied

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