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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Synthesis of Some New Tetrahydropyrimidine Derivatives as Possible Antibacterial Agents

From Wikipedia, the free encyclopedia. After reaction completion, the reaction mass was cooled and treated with crushed ice. The abbreviations used are as follows: Graphical abstract figure shows the ring opening of certain Biginelli pyrimidines using hydrazine.

InAtwal et al. View at Google Scholar T.

Synthesis and evaluation of some new fluorinated hydroquinazoline derivatives as antifungal agents. Kabil5 Nasser S.

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: Culture was carried out with sterile swab and microtube suspension was cultured for 24 h and then inoculated onto Mueller Hinton agar.


Competitive multicomponent Biginelli vs.

Cephalexin was used as the standard antibacterial agent. Chemical shifts are expressed in values ppm using the solvent peak as internal standard. Michaels, Antibiotics Annualvol. The Biginelli Condensation Revisited”. The synthetic pathway for preparation pyrimidins tetrahydropyrimidine derivatives 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 ].

Biginelli Reaction

Eldehna2 Hazem A. An improved synthesis of Biginelli-type compounds via phase-transfer catalyst. In this method, concentration of 10, 20, 30, 50, ……. Retrieved from ” https: The Biginelli reaction is one of the simple and direct methods for the synthesis of tetrahydropyrimidines, originally reported by Biginelli 7.

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. The proposed mechanism for the reaction of DHPM derivatives 4a — 4h with hydrazine hydrate. However, C5 esters reacted with hydrazine hydrate, in ethyl alcohol and in the presence of H 2 SO 4to give hydrazides 5 [ 3738 ] Figure 1.

MIC value was defined as lowest concentration of compound for inhibition growth of the tested bacteria.

Biginelli reaction – Wikipedia

Some of these compounds such as 8 and 10 exhibited a good to significant antibacterial activity. We studied the action of hydrazine hydrate as N -nucleophile on Biginelli pyrimidine esters 4a — 4h. The remaining solid was filtered, washed with water and ethanol and it was consequently dried and recrystallized using ethanol. In general terms, this report is going to describe the synthesis of new tetrahydropyrimidine derivatives via the Biginelli reaction using HCl or DABCO as a catalyst in ethanol.


Reaction Kinetics and Catalysis Letters.

De Oliveira et al. Compounds 2 and 8 showed considerable inhibitory activity against P. In the light of pyrimidnie data and in continuation of our interest in the chemistry of hydrazine hydrate towards certain heterocycles [ 44 — 48 ], we aim herein to study the solvent-free reaction of hydrazine hydrate on C5 ester Biginelli pyrimidines 4a — 4h Figure 3.

A New Synthesis of Biginelli Compounds

All coupling constant values are given in hertz. Iran J Pharm Res. The nucleophilic addition of urea gives the intermediate 4which quickly dehydrates to give the desired product 5. Experimental Melting points were determined with an Electrothermal digital apparatus and were uncorrected.

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