Synthesis of 3,4‐Dihydropyrimidine‐2(1H)‐thiones and Quinazolin‐4(3H)‐ones over Yb(III)‐Resin Catalyst Under Solvent‐free Conditions

References

• Thompson , M. A. and Ellman , J. A. 1996 . Synthesis and applications of small molecule libraries . Chem. Rev. , 96 ( 1 ) : 555 – 600 .
   PubMed Web of Science ®Google Scholar
• Coffen , D. L. Ed. 1998 . Solution phase Combinatory chemistry . Tetrahedron , 54 : 3955 – 4150 .
   Google Scholar
• Kobayashi , S. and Nagayama , S. 1996 . A new methodology for combinatorial synthesis. Preparation of diverse quinoline derivatives using a novel polymer‐supported scandium catalyst . J. Am. Chem. Soc. , 118 ( 37 ) : 8977 – 8978 .
   Google Scholar
• Chen , R. and Qian , C. 2002 . Recent advances in organic reactions catalyzed by lanthanides(III) complexes . Chin. J. Chem. , 20 ( 5 ) : 407 – 419 .
   Google Scholar
• Molander , G. 1992 . Application of lanthanide reagents in organic synthesis . Chem. Rev. , 92 ( 1 ) : 29 – 68 .
   Web of Science ®Google Scholar
• Chen , R. and Qian , C. 2002 . One‐pot sythesis of tetrahydroquinolines catalyzed by Dy(OTf)3 in aqueous solution . Synth. Commun. , 32 ( 16 ) : 2543 – 2548 .
   Web of Science ®Google Scholar
• Ma , Y. , Qian , C. , Wang , L. and Yang , M. 2000 . Lanthanide triflate catalyzed Biginelli reaction. One‐pot synthesis of dihydropyrimidinones under solvent‐free conditions . J. Org. Chem. , 65 ( 12 ) : 3864 – 3868 .
   PubMed Web of Science ®Google Scholar
• Ma , Y. , Qian , C. , Xie , M. and Sun , J. 1999 . Lanthanide chloride catalyzed imino Diels‐Alder reaction. One‐pot synthesis of pyrano[3,2‐c]‐ and furo[3,2‐c]quinolines . J. Org. Chem. , 64 ( 17 ) : 6462 – 3467 .
   Web of Science ®Google Scholar
• Yu , L. , Chen , D. , Li , J. and Wang , P. G. 1997 . Preparation, characterization, and synthetic uses of lanthanide(III) catalysts supported on ion exchange resins . J. Org. Chem. , 62 ( 11 ) : 3575 – 3581 .
   Google Scholar
• Kappe , C. O. 1993 . 100 years of the Biginelli dihydropyrimidine synthesis . Tetrahedron , 49 ( 32 ) : 6937 – 7168 .
   Web of Science ®Google Scholar
• Atwal , K. S. , Swanson , B. N. , Unger , S. E. , Floyd , D. M. , Moreland , S. , Hedberg , A. and O'Reilly , B. C. 1991 . 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 . J. Med. Chem. , 34 ( 2 ) : 806 – 811 .
   PubMed Web of Science ®Google Scholar
• Valverde , M. G. , Dallinger , D. and Kappe , C. O. 2001 . Synlett. , 6 : 741
   Google Scholar
• Dondoni , A. and Massi , A. 2001 . Parallel synthesis of dihydropyrimidinones using Yb(III)‐resin and polymer‐supported scavengers under solvent‐free conditions. A green chemistry approach to the Biginelli reaction . Tetrahedron Lett. , 42 ( 45 ) : 7975 – 7978 .
   Web of Science ®Google Scholar
• Wipf , P. and Cunningham , A. 1995 . A solid phase protocol of the biginelli dihydropyrimidine synthesis suitable for combinatorial chemistry . Tetrahedron Lett. , 36 ( 43 ) : 7819 – 7822 .
   Web of Science ®Google Scholar
• Studer , A. , Jeger , P. , Wipf , P. and Curran , D. P. 1997 . Fluorous synthesis: Fluorous protocols for the Ugi and Biginelli multicomponent condensations . J. Org. Chem. , 62 ( 9 ) : 2917 – 2924 .
   PubMedGoogle Scholar
• Bigi , F. , Carloni , S. , Frullanti , B. , Maggi , R. and Sartori , G. 1999 . A revision of the Biginelli reaction under solid acid catalysis . Solvent‐free synthesis of dihydropyrimidines over montmorillonite KSF. Tetrahedron Lett. , 40 ( 17 ) : 3465 – 3468 .
   Web of Science ®Google Scholar
• Chen , R. and Qian , C. 2002 . One‐pot synthesis of 3,4‐dihydropyrimidine‐2(1H)‐thiones catalyzed by La(OTf)3 . Chin. J. Chem. , 20 ( 5 ) : 427 – 430 .
   Google Scholar
• Baker , B. R. , Joseph , J. P. , Schaub , R. E. , McEvoy , F. J. and Williams , J. H. 1953 . An antimalarial alkaloid from hydrangea XV derivatives of 4‐pyrimidone . J. Org. Chem. , 18 ( 2 ) : 133 – 137 .
   Google Scholar
• Kamal , A. , Ramana , K. V. and Rao , M. V. 2001 . Chemoenzymatic Synthesis of Pyrrolo[2,1‐b]quinazolinones: Lipase‐catalyzed resolution of vasicinone . J. Org. Chem. , 66 ( 3 ) : 997 – 1001 .
   PubMedGoogle Scholar
• Kametani , T. , Loc , C. V. , Higa , T. , Koizumi , M. , Ihara , M. and Fukumoto , K. 1977 . Iminoketene cycloaddition. 2. Total syntheses of arborine, glycosminine, and rutecarpine by condensation of iminoketene with amides . J. Am. Chem. Soc. , 99 ( 7 ) : 2306 – 2309 .
   Google Scholar
• Gueyrard , D. , Leoni , O. , Palmieri , S. and Rollin , P. 2001 . A new and rapid access to homochiral 2,3‐dihydro‐oxazolo[2,3‐b]quinazolin‐5‐ones . Tetrahedron: Asymmetry , 12 ( 2 ) : 337 – 340 .
   Google Scholar
• Wang , L. , Xia , J. , Qin , F. , Qian , C. and Sun , J. 2003 . Yb(OTf)3‐catalyzed one‐pot synthesis of quinazolin‐4(3H)‐ones from anthranilic acid, amines and ortho esters (or formic acid) in solvent‐free conditions . Synthesis , 8 : 1241 – 1247 .
   Web of Science ®Google Scholar