The Reactions of Hydrochlorides of 2, 3-Tri (Tetra) Methylene-3, 4-Dihydropyrimidine-4-Ones with N-Bromosuccinimide and Bromine
N. I. Mukarramov, Kh. Z. Khakimova, A. O. Nasrullaev, Kh. U. Khodjaniyazov, Kh. M. Shakhidoyatov
Chemical Science International Journal · pp. 207–215 · Published 24 Dec 2013
10.9734/ACSJ/2014/7060Abstract
Aims: To carry out reactions between hydrochlorides of 2, 3-tri(tetra)methylene-3, 4-dihydropyrimidine-4-ones and N-bromosuccinimide (and/or bromine), to determine way of reactions. Study Design: Official design. Place and Duration of Study: Department of Organic Chemistry, Institute of the Chemistry of Plant Substances (ICPS) between January 2012 and September 2013. Methodology: We have synthesized 6-methyl-2, 3-tri(tetra)methylene-3, 4-dihydropyrimidine-4-ones from ethyl b-aminocrotonate and g-butyro- or d-valerolactames in the presence of different agents, such as РСl5, POCl3 and SOCl2. For convenient operations the oily bases of 6-methyl-2, 3-tri(tetra)methylene-3, 4-dihydropyrimidine-4-ones have been transmuted into the appropriate hydrochlorides. Bromination by equimolar amount of hydrochlorides with N-bromosuccinimide at room temperature in water gives 5-bromo-6-methyl-2, 3-tri(tetra)methylene-3, 4-dihydropyrimidine-4-ones. Treatment of them by bromine resulted in the formation of perbromides. The reactions were monitored and controlled by TLC. Bromine-products were characterized by IR, 1H NMR, mass-spectra determinations and chemical transformation. Results: Electrophilic substitution at C5 atom was successfully carried out when we have used N-bromosuccinimide. Perbromides of 6-methyl-2, 3-tri(tetra)methylene-3, 4-dihydropyrimidine-4-ones were produced when we have used bromine. Perbromides performed to hydrobromides and bromine complexes when we have treatment of them by acetone and NaHCO3 solution respectively. Conclusion: Bromination of hydrochlorides of 6-methyl-2, 3-tri(tetra)methylene-3, 4-dihydropyrimidine-4-ones by N-bromosuccinimide gives 5-bromine-derivatives. Bromination of them by bromine followed to the formation of perbromides of 6-methyl-2, 3-tri(tetra)methylene-3, 4-dihydropyrimidine-4-ones which are performed to hydrobromides and bromine complexes when we have used corresponding treatments.
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