Synthesis of Some Novel Pyrimidine Derivatives and Investigation of their Electrochemical Behavior

Abstract

2-Iminopyrimidines (1a-e) and 2-thioxopyrimidine (2) were synthesized using the Biginelli three component cyclocondensation reaction of an appropriate β-diketone, arylaldehyde, and guanidine (for 1a-e) or thiourea (for 2). The electrochemical properties of the novel systems were investigated by CV and DPV. Moreover, B3LYP/6-31G(d,p) method was applied to the present structures in order to gather some structural and physicochemical data.

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“…Ethyl-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetra hydro pyrimidine-5-carboxylate was prepared by method reported Fabio S. Falsone and C. Oliver Kappe 6 . According to this method, A mixture of ethyl acetoacetate (0.15 mole, 19.7 gm, 99%), benzaldehyde (0.1 mole, 10.6 gm), Urea (0.1 mole, 6.0 gm) and in 250 ml ethanol was refluxed for 3 to 4 hours in presence of few drops of conc.…”

“…4 Therefore, several improved reaction protocols for the synthesis of Biginelli compounds have been reported, either by modification of the classical one-pot Biginelli reaction, novel multi-step methods, use of combinatorial approaches or microwave irradiation techniques. 5 In further years, improvement in Biginelli compounds is done by using different catalysts such as polyphosphate ester (PPE) 6 , Bronsted acids viz. p-toluenesulfonic acid 7 , potassium hydrogen sulphate 8 , chloroacetic acid 9 , titanium (IV) chloride 10 , ruthenium (III) chloride 11 , scandium (III)triflate 12 , Iodine-alumina 13 ,Cobalt(II)acetate 14 ,sulphated zirconia 15 , ferric chloride hexahydrate 16 , MgBr 2 17 , nbcl 5 18 , Lewis acids 19,20 viz.…”

“…Kappe's group has made great contributions in the area of microwave-assisted Biginelli reactions, Kappe has published an effective Biginelli synthesis assisted by microwaves. 48 The original Biginelli reaction was carried out by refluxing a mixture of the three components such as ethyl acetoacetate, benzaldehyde and urea in presence of ethanol catalyzed by small amount of HCl 49 which often resulted in poor to variable yields of desired products (20-70%) 6 . Fabio S. Falsone and C. Oliver Kappe 6 reported a method of preparation of Ethyl-6-methyl-2-oxo-4-phenyl-1, 2, 3, 4-tetra hydropyrimidine-5-carboxylate.…”

NiCo2O4@Ni(BDC) Nano‐Porous Metal–Organic Framework as a Novel Catalyst for the Synthesis of Spiro[indene[1,2‐d]pyrimidine‐ones and Investigation of Their Antimicrobial Activities

“…Several methods have been reported for the synthesis of pyrimidine derivatives which include: the Biginelli type reactions,three‐component condensation of aromatic aldehydes, ethyl cyanoacetate and guanidine nitrate, multicomponent reaction of aromatic aldehydes, dibenzoylmethane, guanidinium carbonate, and three‐component condensation of cyclic ketones, urea/thiourea/guanidine and 1,3‐diones …”

Synthesis, characterization, quantum chemical studies and electrochemical performance of new 4,7-dihydrotetrazolo[1,5-a]pyrimidine derivatives

“…Solutions were deoxygenated by a stream of high purity nitrogen for 15 min prior to the experiments, and during the experiments, nitrogen flow was maintained over the solution. 10…”