172
Views
1
CrossRef citations to date
0
Altmetric
Original Articles

One-pot Synthesis of 5-Unsubstituted 3,4-Dihydropyrimidin-2(1H)-ones from Aldehydes, Ketones, and Urea under Solvent-free Conditions

, &
Pages 242-251 | Received 24 Aug 2014, Accepted 17 Sep 2014, Published online: 29 Jul 2015

REFERENCES

  • Kappe, C.O. “Biologically Active Dihydropyrimidones of the Biginelli-Type—A Literature Survey.” European Journal of Medicinal Chemistry 35 (2000): 1043–52.
  • Sasaki, S., N. Cho, Y. Nara, M. Harada, S. Endo, N. Suzuki, S. Furuya, and M. Fujino. “Discovery of a Thieno[2,3-d]pyrimidine-2,4-dione Bearing a p-methoxyureidophenyl Moiety at the 6-Position: A Highly Potent and Orally Bioavailable Non-Peptide Antagonist for the Human Luteinizing Hormone-Releasing Hormone Receptor.” Journal of Medicinal Chemistry 46 (2003): 113–24.
  • Atwal, K.S., B.N. Swanson, S.E. Unger, D.M. Floyd, S. Moreland, A. Hedberg, and B.C. O’Reilly. “Dihydropyrimidine Calcium Channel Blockers. 3.1 3-Carbamoyl-4-aryl-1,2,3,4-tetrahydro-6-methyl-5-pyrimidinecarboxylic Acid Esters as Orally Effective Antihypertensive Agents.” Journal of Medicinal Chemistry 34 (1991): 806–11.
  • Rovnyak, G.C., K.S. Atwal, A. Hedberg, S.D. Kimball, S. Moreland, J.Z. Gougoutas, B.C. O’Reilly, J. Schwartz, and M.F. Malley. “Dihydropyrimidine Calcium Channel Blockers. 4. Basic 3-substituted-4-aryl-1,4-dihydropyrimidine-5-carboxylic Acid Esters. Potent Antihypertensive Agents.” Journal of Medicinal Chemistry 35(1992): 3254–63.
  • Rovnyak, G.C., S.D. Kimball, B. Beyer, G. Cucinotta, J.D. DiMarco, J. Gougoutas, A. Hedberg, M. Malley, J.P. McCarthy, R. Zhang, and S. Moreland. “Calcium Entry Blockers and Activators: Conformational and Structural Determinants of Dihydropyrimidine Calcium Channel Modulators.” Journal of Medicinal Chemistry 38 (1995): 119–29.
  • Biginelli, P. “Aldehyde-urea Derivatives of Aceto- and Oxaloacetic Acids.” Gazzetta Chimica Italiana 23 (1893): 360–416.
  • Wang, Z.T., L.W. Xu, C.G. Xia, and H.Q. Wang. “Novel Biginelli-Like Three-Component Cyclocondensation Reaction: Efficient Synthesis of 5-unsubstituted 3,4-dihydropyrimidin-2(1H)-ones.” Tetrahedron Letters 45 (2004): 7951–3.
  • Sabitha, G., K.B. Reddy, R. Srinivas, and J.S. Yadav. “Iodotrimethylsilane-Accelerated One-Pot Synthesis of 5-unsubstituted 3,4-dihydropyrimidin-2(1H)-ones: A Novel Procedure for the Biginelli-Like Cyclocondensation Reaction at Room Temperature.” Helvetica Chimica Acta 88 (2005): 2996–9.
  • Kefayati, H., M. Fakhriyannejad, and A.A. Mohammadi. “An Efficient Synthesis of New 3,4-dihydropyrimidin-2(1H)-ones Incorporating A Phenyl Moiety at C-5 and C-6 Catalyzed by TMSCl and Co(OAc)2·4H2O.” Phosphorus Sulfur 184 (2009): 1796–804.
  • Phucho, I.T., A. Nongpiur, R. Nongrum, and R.L. Nongkhlaw. “Synthesis of 3,4-dihydropyrimidin-2(1H)-ones and 3,4,5,6,7,8-hexahydroquinazolin-2(1H)-ones via Three Component Cyclocondensation.” Indian Journal of Chemistry Section B: Organic Chemistry including Medicinal Chemistry 49 (2010): 346–50.
  • Phucho, I.T., S. Tumtin, A. Nongpiur, R. Nongrum, and R.L. Nongkhlaw. “Microwave Assisted Synthesis of 6-methyl-1,2,3,4-tetrahydro-N-aryl-2-oxo-4-arylpyrimidine-5-carboxamide and 3,4-dihydropyrimidin-2(1H)-ones under Solvent Free Conditions.” Journal of Chemical and Pharmaceutical Research, 2 (2010): 214–22.
  • Saini, A., S. Kumar, and J.S. Sandhu. “Aluminium(III) halides Mediated Synthesis of 5-unsustituted 3,4-dihydropyrimidin-2(1H)-ones via Three Component Biginelli-like Reaction.” Indian Journal of Chemistry Section B: Organic Chemistry including Medicinal Chemistry 46 (2007): 1690–4.
  • Ren, Y.M. and C. Cai. “Three-Components Condensation Catalyzed by Molecular Iodine for the Synthesis of 2,4,6-triarylpyridines and 5-unsubstituted-3,4-dihydropyrimidin-2(1H)-ones under Solvent-Free Conditions.” Monatshefte fur Chemie 140 (2009): 49–52.
  • Liang, B., X. Wang, J.X. Wang, and Z.Du. “New Three-Component Cyclocondensation Reaction: Microwave-Assisted One-Pot Synthesis of 5-unsubstituted-3,4-dihydropyrimidin-2(1H)-ones under Solvent-Free Conditions.” Tetrahedron 63 (2007): 1981–6.
  • Phukan, M., M.K. Kalita, and R. Borah. “A New Protocol for Biginelli (or Like) Reaction under Solvent-Free Grinding Method using Fe(NO3)3·9H2O as Catalyst.” Green Chemistry Letters and Reviews 3 (2010): 329–34.
  • Saini, A., S. Kumar, and J.S. Sandhu. “AlCl3 Mediated Three Component Cyclocondensation for the Synthesis of 5-unsubstituted 3,4-dihydropyrimidin-2(1H)-ones.” Indian Journal of Chemistry Section B: Organic Chemistry including Medicinal Chemistry 45 (2006): 684–88.
  • Song, Z.G., X. Wan, and S. Zhao. “A Modified Procedure for the Synthesis of 2,4,5-tri-and 1,2,4,5-tetrasubstituted Imidazoles.” Chemistry of Natural Compounds 48 (2013): 1119–21.
  • Mistry, S.R. and K.C. Maheria. “Synthesis of Diarylpyrimidinones (DAPMs) using Large Pore Zeolites.” Journal of Molecular Catalysis A-Chemical 355 (2012): 210–15.

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.