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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Biginelli reaction – Wikipedia
A reusable catalyst for high-yield synthesis of 3, 4-dihydropyrimidin-2 1H -ones. Chemical shifts are expressed in values ppm using the solvent peak as internal standard.
Facile preparation and resolution of a stable 5-dihydropyrimidinecarboxylic acid. The reported reactions of hydrazine hydrate with pyrimidines 7a —7 c and 9a —9 c.
Synthesis of Some New Tetrahydropyrimidine Derivatives as Possible Antibacterial Agents
In 1 H Bignielli spectra, all of the products showed a singlet peak at about 5. Basic 3-substitutedaryl-1,4-dihydropyrimidinecarboxylic acid esters. Antibacterial activities of compounds 1- 4, 6 and 8- 10 were measured on three gram negative bacteria E. Experimental Melting points were determined with an Electrothermal digital apparatus and were uncorrected. To receive news and publication updates for Journal of Chemistry, enter your email address in the box below.
An Efficient Synthesis of 5-Alkoxycarbonyl- 4-aryl-3,4-dihydropyrimidin-2 1H -ones”. View at Google Scholar C. Atul Kumar has reported first enzymatic synthesis for Biginelli reaction via yeast catalysed protocol in high yields.
An improved synthesis of Biginelli-type compounds via phase-transfer catalyst.
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.
This reaction was reported by Biginelli and Gazz in and was then catalyzed by acids [ 14 ]. Synthesis and antimicrobial activity of some tetrahydro quinolone diones and pyrano[2,3-d]pyrimidine derivatives. 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.
The reaction mechanism of the Biginelli reaction is a series of bimolecular reactions leading to the desired dihydropyrimidinone. The obtained solid product 16a — 16d was filtered, crystallized from ethanol, and finally dried. Received Mar; Accepted Oct. Retrieved from ” https: 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.
The remaining solid was filtered, washed with water and ethanol and it was consequently dried and recrystallized using ethanol. The latter reaction gave three products, none of them being the expected hydrazide 11a — 11h. To examine the antibacterial activity of some synthesized compounds, three gram negative bacteria: El Kerdawy et al. Cephalexin was used as the standard antibacterial agent. Each concentration was repeated 4 times for each of the bacteria and the average results of inhibitory effects are illustrated in Table 1.
The nucleophilic addition of urea gives the intermediate 4which quickly dehydrates to give the desired product 5. The reaction of C5 esters with thiosemicarbazide, in acetone, to afford thiosemicarbazones 6 is reported Figure 1 [ 39 ].
Culture was carried out with sterile swab and microtube suspension was cultured for 24 h and then inoculated onto Mueller Hinton agar. To a solution of DHPMs 4a — h 0.
A New Synthesis of Biginelli Compounds
The previous conclusions encouraged us to suppose a mechanism for ring opening of DHPMs by hydrazine hydrate Figure 3. Recently, we reported a unique behavior of hydrazine hydrate towards certain benzofurans to produce phenolic-based pyrazoles [ 42 ].
The abbreviations used are as follows: Rapid screening of the antimicrobial activity of extracts and natural products. Table 3 Characterization data of tetrahydropyrimidine derivatives This page was last edited on 25 Septemberat