Synthesis of potential pharmaceutically active dihydropyrimidine-2-oxo and their 2-thio analogues

The Biginelli one - pot three-component cyclocondensation was applied to prepare 3, 4 - dihydropyrimidin - 2 (1H) – ones from aldehydes, β-dicarbonyl compounds and urea (or thiourea) using ZnCl2 as a catalyst. The method offers several advantages including short reaction times and easy experimental work up procedures.Bangladesh J. Sci. Ind. Res.53(4), 327-332, 2018

[1]  H. Adibi,et al.  Iron(III) trifluoroacetate and trifluoromethanesulfonate: Recyclable Lewis acid catalysts for one-pot synthesis of 3,4-dihydropyrimidinones or their sulfur analogues and 1,4-dihydropyridines via solvent-free Biginelli and Hantzsch condensation protocols , 2007 .

[2]  Atul Kumar,et al.  An Efficient Bakers′ Yeast Catalyzed Synthesis of 3,4-Dihydropyrimidin-2-(1H)-ones. , 2007 .

[3]  G. Kirsch,et al.  ZrCl4 or ZrOCl2 under neat conditions : Optimized green alternatives for the Biginelli reaction , 2007 .

[4]  Atul Kumar,et al.  An efficient bakers' yeast catalyzed synthesis of 3,4-dihydropyrimidin-2-(1H)-ones , 2007 .

[5]  Yang Yu,et al.  One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones using chloroacetic acid as catalyst. , 2007, Bioorganic & medicinal chemistry letters.

[6]  Q. You,et al.  An efficient and solvent-free one-pot synthesis of dihydropyrimidinones under microwave irradiation , 2007 .

[7]  S. Maradur,et al.  Heteropoly acid catalyzed synthesis of 3,4-dihydropyrimidin-2(1H)-ones , 2007 .

[8]  Jian-Rong Jin,et al.  HBF4-catalyzed Biginelli reaction: One-pot synthesis of dihydropyrimidin-2(1H)-ones under solvent-free conditions , 2007 .

[9]  P. Phukan,et al.  CuI as reusable catalyst for the Biginelli reaction , 2007 .

[10]  B. Carboni,et al.  Phenylboronic acid as a mild and efficient catalyst for Biginelli reaction , 2006 .

[11]  F. Bamoharram,et al.  12-Molybdophosphoric acid: A recyclable catalyst for the synthesis of Biginelli-type 3,4-dihydropyrimidine-2(1H)-ones , 2006 .

[12]  Yijun Huang,et al.  Highly enantioselective Biginelli reaction using a new chiral ytterbium catalyst: asymmetric synthesis of dihydropyrimidines. , 2006, Journal of the American Chemical Society.

[13]  C. Kappe,et al.  The Biginelli Dihydropyrimidine Synthesis , 2004 .

[14]  A. Chakraborty,et al.  In(OTf)3-catalysed one-pot synthesis of 3,4-dihydropyrimidin-2(lH)-ones , 2004 .

[15]  J. S. Sandhu,et al.  A Novel Cu-catalysed Three-component One-pot Synthesis of Dihydro- pyrimidin-2(1H)-ones Using Microwaves under Solvent-free Conditions , 2004 .

[16]  Qiya Zhuang,et al.  A New Biginelli Reaction Procedure Using Potassium Hydrogen Sulfate as the Promoter for an Efficient Synthesis of 3,4-Dihydropyrimidin-2(1H)-one. , 2004 .

[17]  M. G. D’Oca,et al.  Multicomponent Biginelli's synthesis of 3,4-dihydropyrimidin-2(1H)-ones promoted by SnCl2.2H2O , 2004 .

[18]  A. Shaabani,et al.  A reexamination of Biginelli-like multicomponent condensation reaction: One-pot regioselective synthesis of spiro heterobicyclic rings , 2004, Molecular Diversity.

[19]  E. Juaristi,et al.  An enantioselective approach to the Biginelli dihydropyrimidinone condensation reaction using CeCl3 and InCl3 in the presence of chiral ligands , 2003 .

[20]  J. Yadav,et al.  Vanadium(III) chloride catalyzed Biginelli condensation: solution phase library generation of dihydropyrimidin-(2H)-ones☆ , 2003 .

[21]  D. Shi,et al.  One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones using boric acid as catalyst , 2003 .

[22]  A. Sudalai,et al.  Cu(OTf)2: A Reusable Catalyst for High‐Yield Synthesis of 3,4‐Dihydropyrimidin‐2(1H)‐ones. , 2003 .

[23]  M. Abelman,et al.  Cyclic ketones and substituted α-keto acids as alternative substrates for novel Biginelli-like scaffold syntheses , 2003 .

[24]  A. Sudalai,et al.  Cu(OTf)2: a reusable catalyst for high-yield synthesis of 3,4-dihydropyrimidin-2(1H)-ones , 2003 .

[25]  P. Kundu,et al.  One-pot synthesis of dihydropyrimidinones catalysed by lithium bromide: an improved procedure for the Biginelli reaction , 2003 .

[26]  K. Erol,et al.  Synthesis and in vitro calcium antagonist activity of 4-aryl-7,7-dimethyl/1,7,7-trimethyl-1,2,3,4,5,6,7,8-octahydroquinazoline-2,5-dione derivatives. , 2003, Farmaco.

[27]  Tong‐Shuang Li,et al.  p‐Toluenesulfonic Acid‐Catalyzed Efficient Synthesis of Dihydropyrimidines: Improved High Yielding Protocol for the Biginelli Reaction. , 2002 .

[28]  Shan-Wei Wang,et al.  Indium(III) bromide-catalyzed preparation of dihydropyrimidinones: improved protocol conditions for the Biginelli reaction , 2002 .

[29]  C. Kappe,et al.  Chiral separation of pharmacologically active dihydropyrimidinones with carboxymethyl‐ β‐cyclodextrin , 2001, Electrophoresis.

[30]  C. Kappe Recent Advances in the Biginelli Dihydropyrimidine Synthesis. New Tricks from an Old Dog , 2001 .

[31]  G. Byk,et al.  New regioselective multicomponent reaction: one pot synthesis of spiro heterobicyclic aliphatic rings. , 2000, Journal of combinatorial chemistry.

[32]  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.

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

[34]  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 .

[35]  J. Clark,et al.  Environmentally friendly catalytic methods , 1997 .

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

[37]  S. Moreland,et al.  Dihydropyrimidine calcium channel blockers. 4. Basic 3-substituted-4-aryl-1,4-dihydropyrimidine-5-carboxylic acid esters. Potent antihypertensive agents. , 1992, Journal of medicinal chemistry.

[38]  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.