Synthesis of Nitrogen-Containing Chalcone Via One-Pot Three-Component Reaction: Part IV
Anwar E. M. Nor-Eljaleel
Department of Chemistry, Faculty of Science, Omdorman Islamic University, Khartoum, Sudan
Himat M. A. Fadul
Department of Chemistry, Faculty of Science, Omdorman Islamic University, Khartoum, Sudan
Saad M. H. Ayuob
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, El-Neeilain University, Khartoum, Sudan
M. Abdel Karim
Department of Chemistry, Sudan University of Science and Technology, Faculty of Science, Khartoum, Sudan
Jan H. van der Westhuizen
Department of Chemistry, Faculty of Agriculture, University of Free state, Bloemfontein, South Africa
M. J. A. Abualreish *
Department of Chemistry, Faculty of Science, Omdorman Islamic University, Khartoum, Sudan and Department of Chemistry, Faculty of Science, Northern Border University, Arar, Kingdom of Saudi Arabia
*Author to whom correspondence should be addressed.
Abstract
The mannich reaction is one of the most important C-C bond formation methods in organic synthesis. The mannich-reaction is employed in the organic synthesis of natural compounds like for instance peptides-nucleotides-antibiotics and alkaloids. Other application are in agrochemicals such as plant growth regulators, paint and other polymer chemistry, catalysts and cross linking. The mannich reaction is also used in synthesis of medicinal compounds.
The compound 4-Hydroxy-4'-methoxychalcone was prepared by reacting 4-hydroxybenzaldehyde with 4-methoxyacetophenone. The aminomethylation of this chalcone was accomplished by reaction with formaldehyde and suitable amine in acetonitrile to obtain 4-hydroxy-4'-methoxy-3,5-bis-dimethylaminomethylchalcone(2) 4-hydroxy-4'-methoxy-3, 5-bis-pyrrolidinomethylchalcone(3) and4-hydroxy-4'-methoxy-3, 5-bis-piperdinomethylchalcone(4). The products were purified by column and thin layer chromatography and were identified along with their intermediates by spectroscopic methods: UV, IR, and NMR and mass spectrometry.
Keywords: Chalcones, mannich bases, aminoalkylation, three components reaction