2000
DOI: 10.1021/jo005512a
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A New Substrate for the Biginelli Cyclocondensation:  Direct Preparation of 5-Unsubstituted 3,4-Dihydropyrimidin-2(1H)-ones from a β-Keto Carboxylic Acid

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Cited by 90 publications
(41 citation statements)
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References 22 publications
(12 reference statements)
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“…Finally, the spectrum contains several signals at 6.88, 7.11 and 7.20 ppm for phenyl group; at 7.05, 7.41-7.75 ppm for naphtol group. The 13 ppm for carbons of phenyl group were found. In addition, the presence of 4 was further confirmed from mass spectrum which showed a molecular ion at m/z 292.…”
Section: Resultsmentioning
confidence: 95%
See 1 more Smart Citation
“…Finally, the spectrum contains several signals at 6.88, 7.11 and 7.20 ppm for phenyl group; at 7.05, 7.41-7.75 ppm for naphtol group. The 13 ppm for carbons of phenyl group were found. In addition, the presence of 4 was further confirmed from mass spectrum which showed a molecular ion at m/z 292.…”
Section: Resultsmentioning
confidence: 95%
“…The most widely practiced methodemploys boric acid 10 , silica sulfuric acid 11 , poly(4-vinylpyridine-codivynylbenzene)-Cu(II) complex 11 ,H 2 SO 4 12 , silica triflate 13 and phosphorus pentoxide 14 . Nevertheless,despite its wide scope, the former protocols suffer from several drawbacks e.g.,some reagents have a limited stability and its preparation can be dangerous.Analyzing these data, in this study several straightforward routesare reported for the synthesis of three naphtolderivatives.…”
Section: Resultsmentioning
confidence: 99%
“…Biginelli reaction takes place by mixing different substituted aldehydes, urea or thiourea, and an active 1,3-dicarbonyl compound in combination with different catalytic systems such as AcOH [14], ZrCl 4 [15], Cu(OTf) 2 [16], SiO 2 /H 2 SO 4 [17], La(OTf) 3 [18], CdCl 2 [19], 1-n-butyl-3-methyl imidazolium tetrafluoroborate [20], SiO 2 /NaHSO 4 [21], Pb(NO 3 ) 2 [22], NaCl [23], KSF clay [24], FeCl 3 [25], BiCl 3 [26], ion-exchange resin [27], LiBr [28] [32], Mn(OAc) 3 [33], InBr 3 [ 34], microwave [35][36][37][38] or ultrasound irradiation [39] and solvent-free conditions [40], Co(NO 3 ) 2 .6H 2 O [41], ZnCl 2 /TBAB [42]. In the last two decades microwave mediated reactions have been of great interest in organic synthesis because of their shorter reaction times and high yields of products with good selectivity.…”
Section: Introductionmentioning
confidence: 99%
“…Recently, many reviews [8,9] and papers for preparing these compounds have been reported including classical conditions, with microwave and ultrasound irradiation and by using some other different catalysts such as phosphorus pentoxide-methanesulfonic acid [10], potassium terbutoxide (t-BuOK) [11], ammonium dihydrogen phosphate [12], silicagel [13], mesoporous molecular sieve MCM-41 [14], cyanuric chloride [15], nano-BF 3 ⋅SiO 2 [16], silica gel-supported polyphosphoric Acid [17], zirconium(IV) chloride [18], indium(III) bromide [19], ytterbium(III)-resin [20], 1-nbutyl-3-methylimidazolium tetrafluoroborate (BMImBF 4 ) or hexafluorophosphorate (BMImPF 6 ) [21], ceric ammonium nitrate (CAN) [22], Mn(OAc) 3 ⋅2H 2 O [23], lanthanide triflate [24], indium(III) chloride [25], lanthanum chloride [26], H 2 SO 4 [27], montmorillonite KSF [28], polyphosphate ester (PPE) [29], BF3-OEt 2 /CuCl/HOAc [30], and conc. HCl [31,32].…”
Section: Introductionmentioning
confidence: 99%