Browsing by Author "ANWAR ELBUSHRA MOHAMMED NORELJALEEL"

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    Synthesis of Chalcones with Mannich Side Chain
    (Al Neelain University, 2011) ANWAR ELBUSHRA MOHAMMED NORELJALEEL
    Nineteen new compounds (chalcone with Mannich side chain) were synthesized in this work, together with their intermediates. Aminomethylation of vanillin was achieved by reaction of formaldehyde with various amines (pyrrolidine, piperidine, moropholine, N-methylpiperazine, and N- ethylpiperazine) in dioxane to obtain 4-hydroxy-3-methoxy-5-pyrrolidinomethyl- benzaldehyde (1), 4-hydroxy-3-methoxy-5-piperidinomethylbenzaldehyde (2) 4- hydroxy-3-methoxy-5-morpholinomethylbenzaldehyde (3), 4-hydroxy-3-methoxy-5- N-methylpiperaznomethylbenzaldehyde (4), 5-N-Ethylpiperazinomethyl-4-hydroxy- 3-methoxybe-zaldehyde (5) respectively. These intermediates were reacted with 4- methoxyacetophenone to obtain chalcones with Mannich side chain : 4-Hydroxy-3,4'- dimethoxy-5-pyrrolidinomethylchalcone (6), 4-hydroxy-3,4'-dimethoxy-5- piperlidinomethylchalcone (7), 4-Hydroxy-3,4'-dimethoxy-5-morpholinomethyl chalcone(8),4-hydroxy-3,4'-dimethoxy-5-N-methylpiperazino-methylchalcone (9) , 5- N-ethylpipera-zinomethyl-4-hydroxy-3,4'-dimethoxychalcone (10) The chalcones : 4-hydroxy-4'-methoxychalcone and 4-hydroxy-4'- methoxychalcone were prepared by reacting 3-hydroxy or 4-hydroxybenzaldehyde with 4-methoxyacetophenone . The aminomethylation of chalones was done by reaction with formaldehyde and suitable amines (dimethylamine, pyrrolidine, piperidine, moropholine, N-methylpiperazine, and N-ethylpiperazine) in acetonitrile to obtain 3-hydroxy-4'-methoxy-4-dimethylaminochacone (12), 3-hydroxy-4'- iii methoxy-4-pyrrolidinomethylchalcone (13), 3-hydroxy-4'-methoxy-4-piperlidino- methylchalcone (14), 3-Hydroxy-4'-methoxy-4-morpholinomethylchalcone (15), 3- hydroxy-4'-methoxy-4-( N-methyl-piperazino methyl)chalcone(16),3-hydroxy-4'- methoxy-2,4-bis-(N-methylpiperaz-inomethyl)chalcone (17) and 4-(N- ethylpiperazinomethyl)-3-hydroxy-4'-methoxychalcone(18),4-hydroxy-4'-methoxy- 3,5-bis-dimethylaminomethylchalcone (20), 4-hydroxy-4'-methoxy-3,5-bis- pyrrolidinomethylchalcone (21), 4-hydroxy-4'-methoxy-3,5-bis-piperdinomethyl chalcone (22), 4-hydroxy-4'-methoxy-morpholinomethylchalcone(23), 4-hydroxy-4'- methoxy-3,5-bis-morpholinomethylchalcone(24), 4-hydroxy-4'-methoxy-3,5-bis-N- methylpiperazinomethylchalcone (25), 3-(N-ethylpiperazinomethyl)-4-hydroxy-4'- methoxychalcone (26) 3,5-bis-(N-ethylpiperazinomethyl)-4-hydroxy-4'-methoxy chalcone (27) The final products were purified by thin layer and column chromatography. They were identified along with their intermediates by spectroscopic methods: UV, IR, NMR spectroscopy ( 1 H, 13 C, ABT, COSY, NOESY, HSQC, HMBC) and Mass spectrometry