H₆P₂W₁₈O₆₂-18H₂O, a Green and Reusable Catalyst for the Three-Component, One-Pot Synthesis of 4,6-Diarylpyrimidin-2(1H)-ones Under Solvent-Free Conditions

REFERENCES

• Weber , L. The application of multi-component reactions in drug discovery . Curr. Med. Chem. 2002 , 9 , 2085 .
   PubMed Web of Science ®Google Scholar
• Evans , D. A. ; Tedrow , J. S. ; Shaw , J. T. ; Downey , W. Diastereoselective magnesium halide-catalyzed anti-aldol reactions of chiral N-acyloxazolidinones . J. Am. Chem. Soc. 2002 , 124 , 392 .
   PubMedGoogle Scholar
• Sharma , A. K. ; Jayakumar , S. ; Hundal , M. S. ; Mahajan , M. P. Tandem sigmatropic shifts in [4 + 2] cycloaddition reactions of 1,3-diazabuta-1,3-dienes with butadienylketene: Synthesis of pyrimidinone derivatives . J. Chem. Soc., Perkin Trans. 1 2002 , 774 , and references cited therein .
   Google Scholar
• Sasaki , S. ; Cho , N. ; Nara , Y. ; Harada , M. ; Endo , S. ; Suzuki , N. ; Furuya , S. ; Fujino , M. 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 . J. Med. Chem. 2003 , 46 , 113 .
   PubMed Web of Science ®Google Scholar
• Li , L. H. ; Wallace , T. L. ; Richard , K. A. ; Tracey , D. E. Mechanism of antitumor action of pyrimidinones in the treatment of B16 melanoma and P388 leukemia. Cancer Res. 1985, 45, 532.
   PubMed Web of Science ®Google Scholar
• Bartolini , S. ; Mai , A. ; Artico , M. ; Paesano , N. ; Rotili , D. ; Spadafora , C. ; Sbardella , G. J. 6-[1-(2,6-Difluorophenyl)ethyl]pyrimidinones antagonize cell proliferation; and induce cell differentiation by inhibiting (a nontelomeric) endogenous reverse transcriptase . Med. Chem. 2005 , 48 , 6776 .
   Google Scholar
• Khosropour , A. R. ; Mohammadpoor-Baltork , I. ; Ghorbankhani , H. Bi(TFA)3 immobilized in [nbpy]FeCl4: An efficient catalyst system for the one-pot synthesis of 4,6-diarylpyrimidin-2(1H)-ones . Catal. Commun. 2006 , 7 , 713 .
   Web of Science ®Google Scholar
• Nishiwaki , N. ; Wakamura , E. ; Nishida , Y. ; Tohda , Y. ; Ariga , M. Facile synthesis of functionalized nitroenamines, 2: Ring-opening reaction of hydrated 1-methyl-5-nitropyrimidin-4(1H)-one . Heterocycl. Commun. 1996 , 2 , 129 .
   Google Scholar
• Sedova , V. F. ; Shkurko , O. P. Two directions of the reaction of 4-bromobenzaldehyde with substituted acetophenones and urea: Synthesis of aryl- substituted pyrimidin-2-one and hexahydropyrimido[4,5-d]pyrimidin-2,7-dione . Chem. Heterocycl. Compd. 2004 , 40 , 194 .
   Google Scholar
• Nishiwaki , N. ; Tohda , Y. ; Ariga , M. Nitropyrimidinones: Synthetic equivalents of diformylamine and nitromalonaldehyde . Synthesis 1997 , 1277 .
   Google Scholar
• Clark , J. H. ; Rhodes , C. N. Clean Synthesis Using Porous Inorganic Solid Catalysts and Supported Reagents ; Royal Society of Chemistry : Cambridge , 2000 .
   Google Scholar
• Mizuno , N. ; Misono , M. Heterogeneous Catalysis . chem. Rev. 1998 , 98 , 199 .
   PubMed Web of Science ®Google Scholar
• Briand , L. E. ; Baronetti , G. T. ; Thomas , H. The state of the art on Wells–Dawson heteropoly compounds: A review of their properties and applications . J. Appl. Catal. A: Gen. 2003 , 256 , 37 .
   Web of Science ®Google Scholar
• Romanelli , G. P. ; Baronetti , G. ; Thomas , H. J. ; Autino , J. C. Efficient method for tetrahydropyranylation/depyranylation of phenols and alcohols using a solid acid catalyst with Wells–Dawson structure . Tetrahedron Lett. 2002 , 43 , 7589 .
   Web of Science ®Google Scholar
• Romanelli , G. P. ; Thomas , H. J. ; Baronetti , G. T. ; Autino , J. C. Solvent-free catalytic preparation of 1,1-diacetates from aldehydes using a Wells–Dawson acid (H6P2W18O62·24H2O) . Tetrahedron Lett. 2003 , 44 , 1301 .
   Web of Science ®Google Scholar
• Baronetti , G. ; Briand , L. ; Sedran , U. ; Thomas , H. Heteropolyacid-based catalysis. Dawson acid for MTBE synthesis in gas phase . Appl. Catal. A: Gen. 1998 , 172 , 265 .
   Web of Science ®Google Scholar
• Heravi , M. M. ; Ranjbar , L. ; Derikvand , F. ; Bamoharram , F. F. H6P2W18O62: An efficient and reusable catalyst for one-pot synthesis of β-acetamido ketone and esters . Catal. Commun. 2007 , 8 , 289 .
   Web of Science ®Google Scholar
• Heravi , M. M. ; Derikvand , F. ; Ranjbar , L. ; Oskooie , H. A. ; Bamoharram , F. F. H14[NaP5W30O110] as a heterogeneous recyclable catalyst for the synthesis of 1,5-benzodiazepines . J. Mol. Catal. A: Chem. 2007 , 261 , 156 .
   Web of Science ®Google Scholar
• Heravi , M. M. ; Derikvand , F. ; Bamoharram , F. F. Highly efficient, four-component one-pot synthesis of tetrasubstituted imidazoles using Keggin-type heteropolyacids as green and reusable catalysts . J. Mol. Catal. A: Chem. 2007 , 263 , 112 .
   Web of Science ®Google Scholar
• Heravi , M. M. ; Ranjbar , L. ; Derikvand , F. ; Bamoharram , F. F. A modified and green Dakin–West reaction: An efficient and convenient method for a one-pot synthesis of β-acetamido carbonyl compounds . J. Mol. Catal. A: Chem. 2007 , 271 , 28 .
   Web of Science ®Google Scholar
• Heravi , M. M. ; Khorasani , M. ; Derikvand , F. ; Oskooie , H. A. ; Bamoharram , F. F. Highly efficient synthesis of coumarin derivatives in the presence of H14[NaP5W30O110] as a green and reusable catalyst . Catal. Commun. 2007 , 8 , 1886 .
   Web of Science ®Google Scholar
• Heravi , M. M. ; Ranjbar , L. ; Derikvand , F. ; Alimadadi , B. Three-component one-pot synthesis of 4,6-diarylpyrimidin-2(1H)-ones under solvent-free conditions in the presence of sulfamic acid as a green and reusable catalyst . Mol. Divers. 2008 , 12 , 191 .
   PubMed Web of Science ®Google Scholar
• Baronetti , G. T. ; Briand , L. E. ; Sedran , U. ; Thomas , H. J. Appl. Catal. A: Gen. 1998, 172, 265.
   Web of Science ®Google Scholar
• Liang , B. ; Wang , X. ; Wang , J.-X. ; Du , Z. New three-component cyclocondensation reaction: Microwave-assisted one-pot synthesis of 5-unsubstituted-3,4-dihydropyrimidin-2(1H)-ones under solvent-free conditions . Tetrahedron 2007 , 63 , 1981 .
   Web of Science ®Google Scholar