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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To examine the antibacterial activity of some synthesized compounds, three gram negative bacteria: Cephalexin was used as the standard. The obtained solid product 16a — 16d was filtered, crystallized from ethanol, and finally dried. These facts showed the reactivity of sp 2 C6 of pyrimidines pyrimdine hydrazine hydrate and, subsequently, the ring opening of pyrimidine moiety.

Tetrahydropyrimidine, antimicrobial activity, Biginelli reaction. Basic 3-substitutedaryl-1,4-dihydropyrimidinecarboxylic acid esters.

To receive news and publication updates for Journal of Chemistry, enter your email address in the box below. 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.

Facile preparation and resolution of a stable 5-dihydropyrimidinecarboxylic acid. Lanthanide triflate catalyzed Biginelli synthrsis One-pot synthesis of dihydropyrimidinones under solvent-free conditions.

Biginelli Reaction

This reaction was developed by Pietro Biginelli in Eldehna2 Hazem A. Biological activities of synthesis compounds were tested against gram-positive and gram-negative bacteria. This scheme begins with rate determining nucleophilic addition by the urea to the aldehyde. According to Table 3the best results were obtained in the presence of DABCO as a catalyst where the products were achieved with high yields and shorter reaction times. Compounds 2 and 8 showed considerable inhibitory activity against P.


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: Each concentration was repeated 4 times for each of the bacteria and the average results of inhibitory effects are illustrated in Table 1.

Regarding the importance of the Biginelli reaction products, much work on improving the yield and reaction conditions has been actively pursued. Tested compounds were dissolved in dimethyl sulfoxide DMSO for the preparation of stock solution. The structure of 3,4-dihydropyrimidinones DHPMs 4anticancer agent Monastrol, hydrazide 5, and thiosemicarbazone 6.

The synthetic pathway for preparation of tetrahydropyrimidine derivatives After reaction completion, the reaction mass was cooled and treated with crushed ice.

The Biginelli reaction is one of the simple and direct methods for the synthesis of tetrahydropyrimidines, originally reported by Biginelli 7. Normal saline was used for preparation of inoculants having turbidity equal to 0. pyrimirine

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Dimethyl sulfoxide DMSO only, control for compounds and references. An Efficient Synthesis of 5-Alkoxycarbonyl- 4-aryl-3,4-dihydropyrimidin-2 1H -ones”. Dihydropyrimidinones, the products of the Biginelli reaction, are widely used in the pharmaceutical industry as calcium channel blockers, [11] antihypertensive agentsand alphaa-antagonists.

Culture was carried out with sterile swab and microtube suspension was cultured for 24 h and then inoculated onto Mueller Hinton agar. 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 ]. We studied the action of hydrazine hydrate as N -nucleophile on Biginelli pyrimidine esters 4a — 4h.


All coupling constant values are given in hertz. Competitive multicomponent Biginelli vs.

A New Synthesis of Biginelli Compounds

A mixture of DHPMs 4a — 4h 0. Open in a separate window. In other projects Wikimedia Commons. Rapid screening of the antimicrobial activity of extracts and natural products.

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This unexpected result leads us to perform further extensive survey in literature to discover the effect of hydrazine hydrate on pyrimidines other than DHPMs. National Center for Biotechnology InformationU.

Compounds 1, 2, 4 and exhibited remarkable activity against S. View at Pyrimiidne Scholar M. The straight forward synthesis of DHPMs resulted in the discovery of many important agents such as calcium channel modulators, adrenergic receptor antagonists, and mitotic kinesin inhibitors, in addition to anticancer, anti-inflammatory, antimicrobial, and antioxidant activities [ 9 — 13 ].

Except for compound 8, the other compounds did not show any inhibitory activity bigielli E. Table 1 Antibacterial activity of some synthesized compounds inhibition zones, mm. Table of Contents Alerts. The reaction mechanism of the Biginelli reaction is a series of bimolecular reactions leading to the desired dihydropyrimidinone.

Bismuth III -catalyzed synthesis of dihydropyrimidinones: Kabil5 Nasser S.

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.