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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In 1 H NMR spectra, all of the products showed a singlet peak at about 5. The reported reactions of hydrazine hydrate with pyrimidines 7a —7 c and 9a —9 c. The results are shown in Table 2. biginelil
This page was last edited on 25 Septemberat Oliver “The Biginelli Reaction”, in: Tetrahydroprymidines and their derivatives have recently attracted considerable synhtesis thanks to their pharmacological activities such as anticancer 1antiviral 2calcium channel modulation 3 and pyimidine activity 4 – 6. With respect to R 4the reaction works best with aromatic aldehydes [ 31 ].
Graphical abstract figure shows the ring opening of certain Biginelli pyrimidines using hydrazine.
To receive news and publication updates for Journal of Chemistry, enter your email address in the box below. On the other hand, syntuesis R 5 is an ester group, free carboxylic acids can be produced [ 32 — 34 ]. Highly versatile solid phase synthesis of biofunctional 4-aryl-3,4-dihydropyrimidines using resin-bound isothiourea building blocks and multidirectional resin cleavage.
Kabil5 Nasser S.
All coupling constant values are given in hertz. In other projects Wikimedia Commons. Compounds with pyrimidine scaffolds exhibit wide range of diverse pharmacological actions [ 12 ] and biological activities [ 3 ] such as anti-HIV agent Stavudine pgrimidine 4 ], antibiotic Fervennuline [ 5 ], antihypertensive drug Minoxidil [ 6 ], and antibacterial drug Sulfamethazine [ 7 ].
As a part of our research in the synthesis of pyrimidine derivatives containing biological activities, some new tetrahydropyrimidine derivatives were synthesized via Biginelli reaction using HCl or DABCO as a catalyst with good yields.
Syntyesis Biginelli Condensation Revisited”. Table of Contents Alerts. To the best of our knowledge, there are no reports concerned with the accessibility of C6 for the nucleophilic reaction by hydrazine hydrate. Tetrahydropyrimidine, antimicrobial activity, Biginelli reaction.
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.
A New Synthesis of Biginelli Compounds
We also identified malonohydrazide as reaction product besides salicylaldehyde azine upon the reaction of ethyl 2-oxo-2 H -chromenecarboxylate with hydrazine hydrate [ 43 ]. DHPMs can be obtained by few other synthetic protocols [ 9syntbesis — 17 ] and several improvements were made to obtain good reaction conditions and better yields [ 1118 — 27 ]. The solvent control was included, although no antibacterial activity has been noted.
An improved synthesis of Biginelli-type compounds via phase-transfer catalyst. To examine the antibacterial activity of some synthesized compounds, three gram negative bacteria: Biological activities of synthesis compounds were tested against gram-positive and gram-negative bacteria.
A New Synthesis of Biginelli Compounds
As shown in Table 2these compounds exhibited good inhibitory activity against S. View at Google Scholar B. Reaction Kinetics and Catalysis Letters. 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.
Solvent-Free Ring Cleavage Hydrazinolysis of Certain Biginelli Pyrimidines
Mohana Roopan and R. The benzaldehyd derivatives with substitution xynthesis 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 boginelli in the presence of HCl or DABCO as a catalyst under reflux condition to prepare a series of tetrahydropyrimidine derivatives scheme1Table 3.
Biologically active dihydropyrimidones of the Biginelli-type -a literature survey. Basic 3-substitutedaryl-1,4-dihydropyrimidinecarboxylic acid esters. The Biginelli reaction is pyrimidinw 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.
After reaction completion, the reaction mass was cooled and treated with crushed ice. 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.
Cephalexin was used as the standard.