Bismuth Subnitrate Catalyzed Efficient Synthesis of 3,4‐Dihydropyrimidin‐2(1H)‐Ones: An Improved Protocol for the Biginelli Reaction

Abstract An efficient synthesis of 3,4‐dihydropyrimidinones (DHPMs) using bismuth subnitrate as the catalyst for the first time from an aldehyde, β‐ketoester, and urea in acetonitrile is described. This new method consistently has the advantage of excellent yields (88–96%) and short reaction times (1.5–4 h) than do classical Biginelli reaction conditions.

[1]  Q. Guo,et al.  A Facile and Efficient One‐Pot Synthesis of Dihydropyrimidinones Catalyzed by Magnesium Bromide Under Solvent‐Free Conditions , 2004 .

[2]  Tong‐Shuang Li,et al.  A Simple and Efficient Synthesis of 3,4-Dihydropyrimidin-2-ones Catalyzed by Amidosulfonic Acid. , 2002 .

[3]  M. Mahesh,et al.  Zirconium(IV) chloride catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones☆ , 2002 .

[4]  Tong‐Shuang Li,et al.  A Simple and efficient Synthesis of 3,4-Dihydropyrimidin-2-Ones catalysed by Amidosulfonic Acid † , 2002 .

[5]  Jun Lu,et al.  Catalysis of the Biginelli Reaction by Ferric and Nickel Chloride Hexahydrates. One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones , 2002 .

[6]  M. Alam,et al.  Bismuth triflate catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2 (1H)-ones: An improved protocol for the Biginelli reaction , 2002 .

[7]  Jiajian Peng,et al.  Ionic liquids catalyzed Biginelli reaction under solvent-free conditions , 2001 .

[8]  K. Ramalinga,et al.  Bismuth(III)-Catalyzed Synthesis of Dihydropyrimidinones: Improved Protocol Conditions for the Biginelli Reaction , 2001 .

[9]  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.

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

[11]  S. Buchwald,et al.  Efficient kinetic resolution in the asymmetric hydrosilylation of imines of 3-substituted indanones and 4-substituted tetralones. , 2000, The Journal of organic chemistry.

[12]  Rajender S. Varma,et al.  Microwave-Assisted High-Speed Parallel Synthesis of 4-Aryl-3,4-dihydropyrimidin-2(1H)-ones using a Solventless Biginelli Condensation Protocol , 1999 .

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

[14]  C. Kappe,et al.  Polyphosphate Ester-Mediated Synthesis of Dihydropyrimidines. Improved Conditions for the Biginelli Reaction , 1998 .

[15]  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 .

[16]  A. Khalik,et al.  A Convenient Synthesis of Thiazolopyrimidines, Thiazolodipyrimidines and Heterocyclothiazolopyrimidines. , 2010 .

[17]  Rajive Gupta,et al.  Improved Syntheses of Some Ethyl 4‐Aryl‐6‐methyl‐1,2,3,4‐ tetrahydropyrimidin‐2‐one/thione‐5‐carboxylates by Microwave Irradiation. , 1995 .

[18]  Rongan Zhang,et al.  Calcium entry blockers and activators: conformational and structural determinants of dihydropyrimidine calcium channel modulators. , 1995, Journal of medicinal chemistry.

[19]  S. Sherif,et al.  A convenient synthesis of thiazolopyrimidines, thiazolodipyrimidines and heterocyclothiazolopyrimidines , 1993 .

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

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