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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The abbreviations used are as follows: Iran J Pharm Res. The nucleophilic addition of urea gives the intermediate 4which quickly dehydrates to give the desired product 5. Ghabbour3,4 Maha M. Some of these compounds such as 8 and 10 exhibited a good to significant antibacterial activity.
View at Google Scholar K. An improved synthesis of Biginelli-type compounds via phase-transfer catalyst. Dimethyl sulfoxide DMSO only, control for compounds and references. From Wikipedia, the free encyclopedia. Abstract Heterocyclic compounds containing a pyrimidine nucleus are of special interests thanks to their applications in medicinal chemistry as they are the basic skeleton of several bioactive compounds such as antifungal, antibacterial, antitumor and antitubercular.
Views Read Edit View history. Experimental Melting points were determined with an Electrothermal digital apparatus and were uncorrected. Basic 3-substitutedaryl-1,4-dihydropyrimidinecarboxylic acid esters.
Synthesis of selectively functionalized 2-hetero-1,4-dihydropyrimidines. Chemical shifts are expressed in values ppm using the solvent peak as internal standard.
Interestingly, the reported findings revealed that the hydrazinolysis of pyrimidine-2 1 H -one 7a4-methylpyrimidin-2 1 H -one 7bor 4,6-dimethylpyrimidin-2 1 H -one 7c resulted in the formation of 1 H -pyrazole 8a3-methyl-1 H -pyrazole 8b and 3,5-dimethyl-1 H -pyrazole 8crespectively, in addition to urea 1a in each case Figure 2 [ 40 ]. The solvent control was included, although no antibacterial activity has been noted. The reported reactions of hydrazine hydrate with pyrimidines 7a —7 c and 9a —9 c.
Solvent-Free Ring Cleavage Hydrazinolysis of Certain Biginelli Pyrimidines
The previous conclusions encouraged us to suppose a mechanism for ring opening of DHPMs by hydrazine hydrate Figure 3. In this method, concentration of 10, 20, 30, 50, ……. In 1 H NMR spectra, all of the products showed a singlet peak at about 5. All coupling constant values are given in hertz.
This pyrinidine an synthesi access article distributed under the Creative Commons Attribution Licensewhich permits unrestricted use, synthrsis, and reproduction in any medium, provided the original work is properly cited. This reaction was reported by Biginelli and Gazz in and was then catalyzed by acids [ 14 ].
Dihydropyrimidinones, the products of the Biginelli reaction, are widely used in the pharmaceutical industry as calcium channel blockers,  antihypertensive agentsand alphaa-antagonists.
Atul Kumar has reported first enzymatic synthesis for Biginelli reaction via yeast catalysed protocol in high yields.
Performance standards for antimicrobial susceptibility testing. Subscribe to Table of Contents Alerts. The straight forward synthesis of DHPMs resulted in the discovery of many important agents such as calcium channel modulators, aynthesis receptor antagonists, and mitotic kinesin inhibitors, in addition to anticancer, anti-inflammatory, antimicrobial, and antioxidant activities [ 9 — biginello ].
Retrieved from ” https: This unexpected result leads us to perform further extensive survey in literature to discover the effect of hydrazine hydrate on pyrimidines other than DHPMs. To receive news and publication updates for Journal of Chemistry, enter your email address in the box below.
Introduction Tetrahydroprymidines and their derivatives have recently attracted considerable interest thanks to their pharmacological activities such as anticancer 1antiviral 2calcium channel modulation 3 and antibacterial activity 4 – 6. After reaction completion, the reaction mass was cooled and treated with 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 ]. Table 1 Antibacterial activity of some synthesized compounds inhibition zones, mm.
We also identified malonohydrazide as reaction product besides salicylaldehyde azine upon the reaction of ethyl 2-oxo-2 H -chromenecarboxylate with hydrazine hydrate [ 43 ]. Indexed in Science Citation Index Expanded. National Center for Biotechnology InformationU. The broad absorption band for stretching vibration of NH groups was detected in the region cm Two singlet peaks for NH groups in pyrimidine ring were observed at about Bismuth III -catalyzed synthesis of dihydropyrimidinones: Each concentration was repeated 4 times for each of the bacteria and the average results of inhibitory effects are illustrated in Table 1.
Graphical abstract figure shows the ring opening of certain Biginelli pyrimidines using hydrazine. A mixture of an ethyl benzoylacetate 1 mmolaromatic aldehyde 1 mmolthiourea 1 mmol and an amount of concentration Hydrochloric acid or DABCO 0.
The synthetic pathway for preparation of tetrahydropyrimidine derivatives bifinelli A reusable catalyst for high-yield synthesis of 3, 4-dihydropyrimidin-2 1H -ones. DHPMs can be obtained by few other synthetic protocols [ 915 — 17 ] and several improvements were made to obtain good reaction conditions and better yields [ 1118 — 27 ].
The structure of 3,4-dihydropyrimidinones DHPMs 4anticancer agent Monastrol, hydrazide 5, and thiosemicarbazone 6. Tetrahydroprymidines and their derivatives have recently attracted considerable interest thanks to their pharmacological activities such as anticancer 1antiviral 2calcium channel modulation 3 and antibacterial activity 4 – 6.
Results and Discussion The benzaldehyd derivatives with substitution in aromatic ring with 4-chloro, 3,4-dimethox, 4-methoxy, 4-methyl, 3-nitro, 2-hydroxy, 5-bromohydroxy, 4-isopropyl and 4-hydroxy groups were reacted with thiourea and ethyl benzoylacetate in the presence of HCl or DABCO as a catalyst under reflux condition to prepare a series of tetrahydropyrimidine derivatives scheme1Table 3.