Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 8
423
Views
27
CrossRef citations to date
0
Altmetric
Original Articles

New Procedure for One‐Pot Synthesis of 3,4‐Dihydropyrimidin‐2(1H)‐ones by Biginelli Reaction

, &
Pages 1299-1310 | Received 16 Aug 2007, Published online: 17 Apr 2008

References

  • Kappe , C. O. 1993 . 100 years of the Biginelli dihydropyrimidine synthesis . Tetrahedron , 49 : 6937 – 6963 .
  • Kappe , C. O. and Fabian , W. M.F. 1997 . Conformational analysis of 4‐aryl‐dihydropyrimidine calcium channel modulators. A comparison of ab initio, semiempirical and X‐ray crystallographic studies . Tetrahedron , 53 : 2803 – 2816 .
  • Atwal , K. S. , Roonyak , G. C.O. and Schwartz , B. C. 1989 . Substituted 1,4‐dihydropyrimidines. 3. Synthesis of selectively functionalized 2‐hetero‐1,4‐dihydropyrimidines . J. Org. Chem. , 54 : 5898 – 5907 .
  • Patil , A. D. , Kumar , N. V. , Kokke , W. C. , Bean , M. F. , Freyer , A. , De Brosse , J. C. , Mai , S. , Truneh , A. and Faulkner , D. J. 1995 . Novel alkaloids from the sponge Batzella sp.: inhibitors of HIV gp120‐human CD4 binding . J. Org. Chem. , 60 : 1182 – 1188 .
  • Snider , B. B. , Chen , J. , Patil , A. D. and Freyer , A. 1996 . Synthesis of the tricyclic portions of batzelladines A, B and D: revision of the stereochemistry of batzelladines A and D . Tetrahedron Lett. , 37 : 6977 – 6980 .
  • Aron , Z. D. and Overman , L. E. 2004 . The tethered Biginelli condensation in natural product synthesis . Chem. Commun. , : 253 – 265 .
  • Biginelli , P. G. 1893 . Synthesis of tetrahydropyrimidinones by the acid‐catalyzed condensation of an aldehyde, a β‐keto ester and urea . Chim. Ital. , 26 : 447 – 449 .
  • Lu , J. and Bai , Y. 2002 . Catalysis of the Biginelli Reaction by ferric and nickel chloride hexahydrates: one‐pot synthesis of 3,4‐dihydropyrimidin‐2(1H)‐ones synthesis . Synthesis , : 466 – 470 .
  • Bose , D. S. , Fatima , L. and Mereyala , H. B. 2003 . Green chemistry approaches to the synthesis of 5‐alkoxycarbonyl‐ 4‐aryl‐3,4‐dihydropyrimidin‐2(1H)‐ones by a three‐component coupling of one‐pot condensation reaction: comparison of ethanol, water, and solvent‐free conditions . J. Org. Chem. , 68 : 587 – 590 .
  • Kumar , K. A. , Kasthuraiah , M. , Reddy , C. S. and Reddy , C. D. 2001 . Mn(OAc)3 · 2H2O‐mediated three‐component, one‐pot, condensation reaction: an efficient synthesis of 4‐aryl‐substituted 3,4‐dihydropyrimidin‐2‐ones . Tetrahedron Lett. , 42 : 7873 – 7875 .
  • Reddy , C. V. , Mahesh , M. , Raju , P. V.K. , Babu , T. R. and Reddy , V. V.N. 2002 . Zirconium(IV) chloride catalyzed one‐pot synthesis of 3,4‐dihydropyrimidin‐2(1H)‐ones . Tetrahedron Lett. , 43 : 2657 – 2659 .
  • Ranu , B. C. , Hajra , A. and Jana , U. 2000 . 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 . J. Org. Chem. , 65 : 6270 – 6272 .
  • Sun , Q. , Wang , Y. Q. , Ge , Z. M. , Cheng , T. M. and Li , R. T.A. 2004 . Highly efficient solvent‐free synthesis of dihydropyrimidinones catalyzed by zinc chloride synthesis . : 1047 – 1051 .
  • Ramaliga , K. , Vijayalakshmi , P. and Kaimal , T. N.B. 2001 . Bismuth(III)‐catalyzed synthesis of dihydropyrimidinones: improved protocol conditions for the Biginelli reaction . Synlett. , : 863 – 865 .
  • Lu , J. , Bai , Y. , Wang , Z. , Yang , B. and Ma , H. 2000 . One‐pot synthesis of 3,4‐dihydropyrimidin‐2(1H)‐ones using lanthanum chloride as a catalyst . Tetrahedron Lett. , 41 : 9075 – 9078 .
  • De , S. K. and Gibbs , R. A. 2005 . Ruthenium(III) chloride‐catalyzed one‐pot synthesis of 3,4‐dihydropyrimidin‐2‐(1H)‐ones under solvent‐free conditions synthesis . : 1748 – 1750 .
  • Liu , C. J. , Wang , J. D. and Li , Y. P. 2006 . One‐pot synthesis of 3,4‐dihydropyrimidin‐ 2(1H)‐(thio)ones using strontium(II) nitrate as a catalyst . J. Mol. Catal. A: Chem. , 258 : 367 – 370 .
  • Kalita , H. R. and Phukan , P. 2007 . CuI as reusable catalyst for the Biginelli reaction . Catal. Commun. , 8 : 179 – 182 .
  • Gohain , M. , Prajapati , D. and Sandhu , J. S. 2004 . A novel Cu‐catalyzed three‐component one‐pot synthesis of dihydropyrimidiu‐2(1H)‐ones using microwaves under solvent‐free condition . Synlett. , : 235 – 238 .
  • Paraskar , A. S. , DewKar , G. K. and Sudalai , A. 2003 . Cu(OTf)2: a reusable catalyst for high‐yield synthesis of 3,4‐dihydropyrimidin‐2(1H)‐ones . Tetrahedron Lett. , 44 : 3305 – 3308 .
  • Zhang , X. , Li , Y. , Liu , C. and Wang , J. 2006 . An efficient synthesis of 4‐substituted pyrazolyl‐3,4‐dihydropyrimidin‐ 2(1H)‐(thio)ones catalyzed by Mg(ClO4)2 under ultrasound irradiation . J. Mol. Catal A: Chem. , 253 : 207 – 211 .
  • Ghosh , R. , Maiti , S. and Chakraborty , A. 2004 . In(OTf)3‐catalysed one‐pot synthesis of 3,4‐dihydropyrimidin‐2(lH)‐ones . J. Mol. Catal. A: Chem. , 217 : 47 – 50 .
  • Ichiro , S. , Yuko , S. and Takeda , K. 2006 . Metal triflimide as a lewis acid catalyst for Biginelli reactions in water . Tetrahedron Lett. , 47 : 7861 – 7864 .
  • Ma , Y. , Qian , C. , Wang , L. and Yang , M. 2000 . On the conformational properties of [n]cyclophanes: a new application of the ramachandran plot using crystallographic data . J. Org. Chem. , 65 : 3864 – 3849 .
  • Wang , L. , Qian , C. , Tian , H. and Ma , Y. 2003 . Lanthanide triflate catalyzed one‐pot synthesis of dihydropyrimidin‐2(1H)‐thiones by a three‐component of 1,3‐dicarbonyl compounds, aldehydes, and thiourea using a solvent‐free Biginelli condensation . Synth. Commun. , 33 : 1459 – 1468 .
  • Dondoni , A. , Massi , A. , Minghini , E. , Sabbatini , S. and Bertolasi , V. 2003 . Model studies toward the synthesis of dihydropyrimidinyl and pyridyl α‐amino acids via three‐component Biginelli and Hantzsch cyclocondensations . J. Org. Chem. , 68 : 6172 – 6183 .
  • Kobayashi , S. , Wakabayashi , T. , Nagayama and Oyamada , S. H. 1997 . Lewis acid catalysis in micellar systems. Sc(OTf)3‐catalyzed aqueous aldol reactions of silyl enol ethers with aldehydes in the presence of a surfactant . Tetrahedron Lett. , 38 : 4559 – 4562 .
  • Grieco , P. A. 1998 . Organic Synthesis in Water London : Blackie Academic and Professional .
  • Li , C. J. and Chan , T. H. 1997 . Organic Reactions in Aqueous Media 159 New York : John Wiley & Sons .
  • Li , C. J. 2005 . Organic reaction in aqueous media with a focus on carbon‐carbon bond formations: a decade update . Chem. Rev. , 105 : 3095 – 3165 .
  • Lindstrom , U. M. 2002 . Stereoselective organic reactions in water . Chem. Rev. , 102 : 2751 – 2772 .
  • Tascioglu , S. 1996 . Micellar solutions as reaction media. Tetrahedron . 52 : 11113 – 11152 .
  • Holland , P. M. and Rubingh , D. N. 1992 . Mixed Surfactant Systems Washington , D.C. : American Chemical Society .
  • Sabatini , D. A. , Knox , R. and Harwell , C. J. H. 1994 . Surfactant‐Enhanced Subsurface Remediation Washington , D.C. : American Chemical Society .
  • Lu , J. and Ma , H. 2000 . Iron(III)‐catalyzed synthesis of dihydropyrimidinones: improved conditions for the Biginelli reaction . Synlett , : 63 – 64 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.