Ultrasound-accelerated synthesis of 3,4-dihydropyrimidin-2(1H)-ones with ceric ammonium nitrate

Ceric ammonium nitrate efficiently catalyzes the three component condensation of an aldehyde, β-ketoester and urea in methanol to afford the corresponding dihydropyrimidinones in excellent yields under sonication. Other oxidants such as manganese triacetate and Oxone were also found to catalyze this transformation under similar conditions.

[1]  B. Ranu,et al.  Indium(III) chloride-catalyzed one-pot synthesis of dihydropyrimidinones by a three-component coupling of 1,3-dicarbonyl compounds, aldehydes, and urea: an improved procedure for the Biginelli reaction. , 2000, The Journal of organic chemistry.

[2]  C. Qian,et al.  Lanthanide triflate catalyzed Biginelli reaction. one-pot synthesis of dihydropyrimidinones under solvent-free conditions. , 2000, The Journal of organic chemistry.

[3]  Kamaljit Singh,et al.  An expedient protocol of the Biginelli dihydropyrimidine synthesis using carbonyl equivalents , 1999 .

[4]  S. Carloni,et al.  A revision of the Biginelli reaction under solid acid catalysis. Solvent-free synthesis of dihydropyrimidines over montmorillonite KSF , 1999 .

[5]  E. Hu,et al.  Unprecedented Catalytic Three Component One-Pot Condensation Reaction: An Efficient Synthesis of 5-Alkoxycarbonyl- 4-aryl-3,4-dihydropyrimidin-2(1H)-ones , 1998 .

[6]  C. Kappe,et al.  Conformational analysis of 4-aryl-dihydropyrimidine calcium channel modulators. A comparison of ab initio, semiempirical and X-ray crystallographic studies , 1997 .

[7]  T. Mason.  Ultrasound in synthetic organic chemistry , 1997 .

[8]  Jinsheng Chen,et al.  Synthesis of the tricyclic portions of batzelladines A, B and D. Revision of the stereochemistry of batzelladines A and D , 1996 .

[9]  P. Wipf,et al.  A SOLID PHASE PROTOCOL OF THE BIGINELLI DIHYDROPYRIMIDINE SYNTHESIS SUITABLE FOR COMBINATORIAL CHEMISTRY , 1995 .

[10]  M. F. Bean,et al.  Novel Alkaloids from the Sponge Batzella sp.: Inhibitors of HIV gp120-Human CD4 Binding , 1995 .

[11]  C. Kappe.  100 years of the biginelli dihydropyrimidine synthesis , 1993 .

[12]  A Hedberg,et al.  Dihydropyrimidine calcium channel blockers. 3. 3-Carbamoyl-4-aryl-1,2,3,4-tetrahydro-6-methyl-5-pyrimidinecarboxylic acid esters as orally effective antihypertensive agents. , 1991, Journal of medicinal chemistry.

[13]  B. Giese,et al.  Relative Rates for the Addition Reactions of the Malonyl Radical to Substituted Styrenes Induced by Cerium(IV) Ammonium Nitrate and Tributyltin Hydride. A Comparison , 1990 .

[14]  G. Rovnyak,et al.  Substituted 1,4-dihydropyrimidines. 3. Synthesis of selectively functionalized 2-hetero-1,4-dihydropyrimidines , 1989 .

[15]  K. Atwal,et al.  Synthesis of substituted 1,2,3,4-tetrahydro-6-methyl-2-oxo-5-pyrimidinecarboxylic acid esters: the Biginelli condensation revisited , 1987 .

[16]  M. Malley,et al.  Synthesis of substituted 1,2,3,4-tetrahydro-6-methyl-2-thioxo-5-pyrimidinecarboxylic acid esters , 1987 .

[17]  K. Folkers,et al.  Researches on Pyrimidines. CXXXIV. The Reaction of Phenylacetaldehyde and Acetophenone with Urea , 1933 .

[18]  H. Harwood,et al.  RESEARCHES ON PYRIMIDINES. CXXX. SYNTHESIS OF 2-KETO-1,2,3,4-TETRAHYDROPYRIMIDINES , 1932 .