Trifluoroethanol as a Metal-Free, Homogeneous, and Recyclable Medium for the Efficient One-Pot Synthesis of Dihydropyrimidones

REFERENCES

• Armstrong , R. W. ; Combs , A. P. , Tempest , P. A. ; Brown , S. D. ; Keating , T. A. Multiple-component condensation strategies for combinatorial library synthesis . Acc. Chem. Res. 1996 , 29 , 123 – 131 .
   Web of Science ®Google Scholar
• Tietze , L. F. ; Lieb , M. E. Domino reactions for library synthesis of small molecules in combinatorial chemistry . Curr. Opin Chem. Biol. 1998 , 2 , 363 – 371 .
   PubMed Web of Science ®Google Scholar
• Dax , S. L. ; Mcnally , J. J. ; Youngman , M. A. Multi-component methodologies in solid-phase organic synthesis . Curr. Med. Chem. 1999 , 6 , 255 – 270 .
   PubMed Web of Science ®Google Scholar
• Schreiber , S. L. Target-oriented and diversity-oriented organic synthesis in drug discovery . Science 2000 , 287 , 1964 – 1969 .
   PubMed Web of Science ®Google Scholar
• Kappe , C. O. One hundred years of the Biginelli dihydropyrimidine synthesis . Tetrahedron 1993 , 49 , 6937 – 6963 .
   Web of Science ®Google Scholar
• Kappe , C. O. Recent advances in the Biginelli dihydropyrimdine in the Biginelli dihydropyrimidine synthesis: New tricks from an old dog. Acc . Chem. Res. 2000 , 33 ( 12 ), 879 – 888 .
   PubMed Web of Science ®Google Scholar
• Kappe , C. O. Biologically active dihydropyrimidones of the Biginelli type: A literature survey . Eur. J. Med. Chem. 2000 , 35 , 1043 – 1052 .
   PubMed Web of Science ®Google Scholar
• Atwal , K. S. ; Rovnyak , G. C. ; Reilly , B. C. O. ; Schwatrz , J. Substituted 1,4-dihydropyrimidines: Synthesis of selectively functionalized 2-hetero-1,4-dihydropyrimidines. J. Org. Chem. 1989, 54, 5589–5907.
   Web of Science ®Google Scholar
• Kappe , C. O. ; Fabian , W. M. F. ; Semones , M. A. Conformational analysis of 4-aryl-dihydropyrimidine calcium channel modulators. A comparison of ab initio, semiempirical, and x-ray crystallographic studies . Tetrahedron 1997 , 53 , 2803 – 2816 .
   Web of Science ®Google Scholar
• Barrow , J. C. ; Nantermet , P. G. ; Selnick , H. G. In vitro and in vivo evaluation of dihydropyrimidinone C-5 amides as potent and selective α 1A receptor antagonists for the treatment of benign prostatic hyperplasia . J. Med. Chem. 2000 , 43 , 2703 – 2718 .
   PubMed Web of Science ®Google Scholar
• Mayer , T. U. ; Kapoor , T. M. ; Haggarty , S. J. ; King , R. W. ; Schreiber , S. L. ; Mitchison , T. J. Small molecule inhibitor of mitotic spindle bipolarity identified in a phenotype-based screen . Science 1999 , 286 , 971 – 974 .
   PubMed Web of Science ®Google Scholar
• Haggarty , S. J. ; Mayer , T. U. ; Miyamoto , D. T. ; Fathi , R. ; King , R. W. T. J. ; Mitchison , T. J. ; Schreiber , S. L. Dissecting cellular processes using small molecules: Identification of colchicine-like, taxol-like and other small molecules that perturb mitosis . Chem. Biol. 2000 , 7 , 275 – 286 .
   PubMed Web of Science ®Google Scholar
• Paraskar , A. S. ; Dewkar , G. K. ; Sudlai , A. Cu(OTf)2: A reusable catalyst for high-yield synthesis of 3,4-dihydropyrimidin-2(1H)-ones . Tetrahedron Lett. 2003 , 44 , 3305 – 3308 .
   Web of Science ®Google Scholar
• (a) Biginelli , P. G. Aldehyde–urea derivatives of aceto- and oxaloacetic acids . Chim. Ital. 1893 , 23 , 360 – 416 ; (b) Syamala , M. Recent progress in three-component reactions: An update . Org. Prep. Proced. Internat. 2009 , 41 , 1 – 68 ; (c) Saini , A. ; Kumar , S. ; Sandhu , J. S. Biginelli reaction (review) . J. Indian Chem. Soc. 2007 , 84 , 959 – 970 ; (d) Kumaravel , K. ; Vasuki , G. Multicomponent reactions in water . Curr. Org. Chem. 2009 , 13 , 1820 – 1841 .
   Google Scholar
• Peng , J. ; Deng , Y. Ionic–liquids catalyzed Biginelli reaction under solvent-free conditions . Tetrahedron Lett. 2001 , 42 , 5917 – 5919 .
   Web of Science ®Google Scholar
• Hu , E. H. ; Sidler , D. R. ; Dolling , U. H. Unprecedented catalytic three-component one-pot condensation reaction: An efficient synthesis of 5-alkoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones . J. Org. Chem. 1998 , 63 , 3454 – 3457 .
   Web of Science ®Google Scholar
• Ranu , B. C. ; Hajra , A. ; Jana , U. 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. 2000 , 65 , 6270 – 6272 .
   PubMed Web of Science ®Google Scholar
• Lu , J. ; Bai , Y. ; Wang , Z. ; Yang , B. ; Ma , H. One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones using lanthanum chloride as a catalyst . Tetrahedron Lett. 2000 , 41 , 9075 – 9078 .
   Web of Science ®Google Scholar
• Carloni , B. F. ; Frullanti , B. ; Maggi , R. ; Sartori , G. Revision of the Biginelli reaction under solid acid catalysis. Solvent-free synthesis of dihydropyrimidines over montmorillonite KSF . Tetrahedron Lett. 1999 , 40 , 3465 – 3468 .
   Web of Science ®Google Scholar
• Wang , D.-C. ; Guo , H.-M. ; Qu , G.-R. Efficient, green, solvent-free synthesis of 3,4-dihydropyrimidin-2(1H)-ones via Biginelli reaction catalyzed by Cu(NO3)2 · 3H2O: Efficient, green, solvent-free . Synth. Commun. 2010 , 40 ( 8 ), 1115 – 1122 .
   Web of Science ®Google Scholar
• Kumar , K. A. ; Kashthuraiahm , M C. ; Reddy , S. ; Reddy , C. D. 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. 2001 , 42 , 7873 – 7875 .
   Web of Science ®Google Scholar
• Yadav , J. S. ; Reddy , B. V. S. ; Srinivas , R. ; Venugopal , C. ; Ramalingam , T. LiClO4-Catalyzed one-pot synthesis of dihydropyrimidinones: An improved protocol for Biginelli reaction . Synthesis 2001 , 1341 – 1345 .
   Web of Science ®Google Scholar
• Bussolari , J. C. ; McDonnell , P. A. A new substrate for the Biginelli cyclocondensation: Direct preparation of 5-unsubstituted 3,4-dihydropyrimidin-2(1H)-ones from a β-keto carboxylic acid . J. Org. Chem. 2000 , 65 , 6777 – 6779 .
   PubMed Web of Science ®Google Scholar
• Zhang , M. ; Li , Y. Q. Facile one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-one catalyzed by Zn(NH2SO3)2 . Synth. Commun. 2006, 36, 835–841.
   Web of Science ®Google Scholar
• Fu , N. Y. ; Yuan , Y. F. ; Cao , Z. ; Wang , S. W. ; Wang , J. T. ; Peppe , C. Tetrahedron 2002 , 58 , 4801 – 4807 .
   Web of Science ®Google Scholar
• Lu , J. ; Bai , Y. Catalysis of the Biginelli reaction by ferric and nickel chloride hexahydrates. One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones . Synthesis 2002 , 466 – 470 .
   Web of Science ®Google Scholar
• Hu , E. H. ; Sidler , D. R. ; Dolling , U.-H. Unprecedented catalytic three-component, one-pot condensation reaction: An efficient synthesis of 5-alkoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones . J. Org. Chem. 1998 , 63 , 3454 – 3457 .
   Web of Science ®Google Scholar