Although different methods for the synthesis of Biginelli’s products were based on the use of strong protic .. Pyrimidine and its derivatives. A Mini Review: Biginelli Reaction for the Synthesis of Dihydropyrimidinones. Conference Pyrimidine Containing Derivatives Scheme 7. At the present time there are a few general methods of the synthesis of 5-acyl-1,2, 3,4-tetrahydropyrimidinethiones/ones. One of them is the Biginelli reaction.
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Melting points were determined with synthesus Electrothermal digital apparatus and were uncorrected. Said1 Wagdy M. Retrieved from ” https: The 13 C NMR spectra of these compounds showed a signal at about Al-shakliah3,6 and Hatem A.
Experimental Melting points were determined with an Electrothermal digital apparatus and were uncorrected. View at Google Scholar C.
The reaction mixture was allowed to cool and poured on crushed ice. Pyrimidines of Biginelli type 3,4-dihydropyrimidines, DHPMs showed a broad spectrum of biological activities such as anticancer agent, Monastrol Figure 1 [ 89 ].
A New Synthesis of Biginelli Compounds
This reaction was reported by Biginelli and Gazz in and was then catalyzed by acids [ 14 ]. Correspondence biginrlli be addressed to Hazem A. Compounds 2 and 8 showed considerable inhibitory activity pyrimiidne P. Normal saline was used for preparation of inoculants having turbidity equal to 0.
Kabil5 Nasser S. Facile preparation and resolution of a stable 5-dihydropyrimidinecarboxylic acid. Melting points were measured with a Stuart melting point apparatus and were uncorrected.
Synthesis of Some New Tetrahydropyrimidine Derivatives as Possible Antibacterial Agents
Culture was carried out with sterile swab and microtube suspension was cultured for 24 h and then inoculated onto Mueller Hinton agar. El Kerdawy et al. The remaining solid was filtered, washed with water and ethanol and it was consequently dried and recrystallized using ethanol. This is an open access article distributed under the Creative Commons Attribution Licensewhich permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Iran J Pharm Res. The latter pyyrimidine gave three synthfsis, none of them being the expected hydrazide 11a — 11h. The reported reactions of hydrazine hydrate with pyrimidines 7a —7 c and 9a —9 c.
Journal of Chemistry
MIC value was defined as lowest concentration of compound for inhibition growth of the tested bacteria. A mixture synghesis DHPMs 4a — 4h 0. The authors would like to extend their sincere appreciation to the Deanship of Scientific Research at King Saud University for its funding of this research through the Research Group, Project no. The broad biginelll band for stretching vibration of NH groups was detected in the region cm The results are shown in Table 2.
View at Google Scholar K.
To examine the antibacterial activity of some synthesized compounds, three gram negative bacteria: All coupling constant values are given in hertz.
View at Google Scholar B. Biologically active dihydropyrimidones of the Biginelli-type -a literature survey. Table 3 Characterization data of tetrahydropyrimidine derivatives The solvent control was included, although no antibacterial activity has been noted.
Lanthanide triflate catalyzed Biginelli reaction One-pot synthesis of dihydropyrimidinones under solvent-free conditions. InAtwal et al. Table 1 Antibacterial activity of some synthesized compounds inhibition zones, mm. Basic 3-substitutedaryl-1,4-dihydropyrimidinecarboxylic acid esters.
Articles from Iranian Journal of Pharmaceutical Research: Synthesis and antimicrobial activity of some tetrahydro quinolone diones and pyrano[2,3-d]pyrimidine derivatives. Atul Kumar has reported first enzymatic synthesis for Biginelli reaction via yeast catalysed protocol in high yields.
Cephalexin was used as the standard. The Biginelli reaction is a multiple-component chemical reaction that creates 3,4-dihydropyrimidin-2 1 H -ones 4 from ethyl acetoacetate 1an aryl aldehyde such as benzaldehyde 2and urea 3. Dimethyl sulfoxide DMSO only, control for compounds and references. Ghabbour3,4 Maha M. On the other hand, when R 5 is an ester group, free carboxylic acids can be produced [ 32 — 34 ].
National Center for Biotechnology InformationU. Heterocyclic compounds containing a pyrimidine nucleus are of special interests thanks to their applications in medicinal chemistry as they are bigibelli basic skeleton of several bioactive compounds such as antifungal, antibacterial, antitumor and antitubercular.
Abstract Certain Biginelli pyrimidines with ester substitution in C5 were subjected to unexpected ring opening upon solvent-free reaction with hydrazine hydrate to give three products: From Wikipedia, the free encyclopedia.
Ring forming reactions Carbon-carbon bond forming reactions Condensation reactions Multiple component reactions Name reactions Nitrogen heterocycle forming reactions. After reaction completion, the reaction mass was cooled and treated with crushed ice. The latter data stimulate our interest to investigate the reactivity of C5 ester towards hydrazine hydrate under solvent-free conditions which produce three different ring cleavage products.
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