Trimethylsilyl Chloride: A Facile and Efficient Reagent for One‐Pot Synthesis of 3,4‐Dihydropyrimidin‐2(1H)‐ones

References

• Kappe , C. O. 1993 . 100 Years of the Biginelli dihydropyrimidine synthesis . Tetrahedron , 49 : 6937
   Web of Science ®Google Scholar
• Rovnyak , G. C. , Kimball , S. D. , Beyer , B. , Cucinotta , G. , Dimarco , J. D. , Gougoutas , J. , Hedberg , A. , Malley , M. , McCarthy , J. P. , Zhang , R. and Moreland , S. 1995 . Calcium entry blockers and activators: conformational and structural determinants of dihydropyrimidine calcium channel modulators . J. Med. Chem. , 38 : 119 [PUBMED] [INFOTRIEVE] [CSA]
   PubMed Web of Science ®Google Scholar
• Atwal , K. S. , Rovnyak , G. C. , Kimball , S. D. , Floyd , D. M. , Moreland , S. , Swanson , B. N. , Gougoutas , J. Z. , Schwartz , J. , Smillie , K. M. and Malley , M. F. 1990 . Dihydropyrimidine calcium channel blockers. II. 3‐Substituted‐4‐aryl‐1, 4‐dihydro‐6‐methyl‐5‐pyrimidinecarboxylic acid esters as potent mimics of dihydropyridines . J. Med. Chem. , 33 : 2629 [PUBMED] [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• Kappe , C. O. and Fabian , W. M.F. 1997 . Synthesis and reactions of Biginelli compounds, 6. Conformational analysis of 4‐aryl‐dihydropyrimidine calcium channel modulators. A comparison of ab initio, semiempirical and x‐ray crystallographic studies . Tetrahedron , 53 : 2803 [CROSSREF]
   Web of Science ®Google Scholar
• Kappe , C. O. 2000 . Biologically active dihydropyrimidones of the Biginelli‐type–a literture survey . Eur. J. Med. Chem. , 35 : 1043 [PUBMED] [INFOTRIEVE] [CSA] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Ranu , B. C. , Hajra , A. U. and Jana , J. 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 . Org. Chem. , 65 : 6270 [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Overman , L. E. , Rabinowitz , M. H. and Renhowe , P. A. 1995 . Enantioselective total synthesis of (−)‐ptilomycalin A . J. Am. Chem. Soc. , 117 : 2657
   Web of Science ®Google Scholar
• Biginelli , P. 1893 . Aldehyde‐urea derivatives of aceto‐ and oxaloacetic acids . Gazz. Chim. Ital. , 23 : 360
   Google Scholar
• Hu , E. H. , Sidler , D. R. and Dolling , U. H. 1998 . 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. , 63 : 3454 [CROSSREF]
   Web of Science ®Google Scholar
• Kappe , C. O. and Falsone , S. F. 1998 . Synthesis and reactions of Biginelli compounds, 12. Polyphosphate ester‐mediated synthesis of dihydropyrimidines. Improved conditions for the Biginelli reaction . Synlett , : 718
   Google Scholar
• Bigi , F. S. , 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 : 3465 [CROSSREF]
   Web of Science ®Google Scholar
• Lu , J. , Ma , H.‐H. and Li , W.‐H. 2000 . A novel one‐pot synthesis of 3,4‐dihydropyrimidin‐2(1H)‐ones by catalyzed ferric chloride hexahydrate . Chin. J. Org. Chem. , 20 : 815 (in Chinese)
   Web of Science ®Google Scholar
• Lu , J. , Wang , F.‐L. , Bai , Y.‐J. and Li , W.‐H. 2002 . Catalysis of the Biginelli reaction by NiCl2·6H2O: one‐pot synthesis of 3,4‐dihydropyrimidin‐2(1H)‐ones . Chin. J. Org. Chem. , 22 : 788 (in Chinese)
   Google Scholar
• 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 [CROSSREF]
   Web of Science ®Google Scholar
• 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 [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• 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 [CROSSREF]
   Web of Science ®Google Scholar
• Ramalinga , K. , Vijayalaxmi , P. and Kaimal , T. N.B. 2001 . Bismuth(III)‐catalyzed synthesis of dihydropyrimidinones: improved protocol conditions for the Biginelli reaction . Synlett , : 863 [CROSSREF]
   Web of Science ®Google Scholar
• 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 [CROSSREF]
   Web of Science ®Google Scholar
• Yadav , J. S. , Reddy , B. V.S. , Srinivas , R. , Venugopal , C. and Ramalingam , T. 2001 . LiClO4‐catalyzed one‐pot synthesis of dihydropyrimidinones: an improved protocol for Biginelli reaction . Synthesis , : 1341 [CROSSREF]
   Web of Science ®Google Scholar
• Jin , T. S. , Zhang , S. L. , Zhang , S. Y. , Guo , J. J. and Li , T. S. 2002 . A simple and efficient synthesis of 3,4‐dihydropyrimidin‐2‐ones catalysed by amidosulfonic acid . J. Chem. Res. (S) , : 37
   Google Scholar
• Peng , J. and Deng , Y. 2001 . Ionic liquids catalyzed Biginelli reaction under solvent‐free conditions . Tetrahedron Lett. , 42 : 5917 [CROSSREF]
   Web of Science ®Google Scholar
• Stadler , A. and Kappe , C. O. 2000 . Microwave‐mediated Biginelli reactions revisited. On the nature of rate and yield enhancements . J. Chem. Soc., Perkin. Trans. 2 , : 1363 [CROSSREF]
   Google Scholar
• Stefani , H. A. and Gatti , P. M. 2000 . 3,4‐Dihydropyrimidin‐2(1H)‐ones: fast synthesis under microwave irradiation in solvent free conditions . Synth. Commun. , 30 : 2165
   Web of Science ®Google Scholar
• Kappe , C. O. , Kumar , D. and Varma , R. S. 1999 . Microwave‐assisted high‐speed parallel synthesis of 4‐aryl‐3,4‐dihydropyrimidin‐2(1H)‐ones using a solventless Biginelli condensation protocol . Synthesis , : 1799 [CROSSREF]
   Web of Science ®Google Scholar
• Kappe , C. O. 2001 . Automated library generation using sequential microwave‐assisted chemistry. Application toward the Biginelli multicomponent condensation . J. Comb. Chem. , 3 : 624 [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMedGoogle Scholar
• Wipf , P. and Cunningham , A. 1995 . A solid phase protocol of the Biginelli dihydroprimidine synthesis suitable for combinatorial chemistry . Tetrahedron Lett. , 36 : 7819 [CROSSREF]
   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 : 2917 [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Varala , R. , Alam , M. and Adapa , S. R. 2003 . Bismuth triflate catalyzed one‐pot synthesis of 3,4‐dihydropyrimidin‐2(1H)‐ones: an improved protocol for the Biginelli reaction . Synlett , : 167
   Google Scholar
• Shaabani , A. , Bazgir , A. and Teimouri , F. 2003 . Ammonium chloride‐catalyzed one‐pot synthesis of 3,4‐dihydropyrimidin‐2‐(1H)‐ones under solvent‐free conditions . Tetrahedron Lett. , 44 : 857 [CROSSREF]
   Web of Science ®Google Scholar
• Maiti , G. , Kundu , P. and Guin , C. 2003 . One‐pot synthesis of dihydropyrimidinones catalyzed by lithium bromide: an improved procedure for the Biginelli reaction . Tetrahedron Lett. , 44 : 2757 [CROSSREF]
   Web of Science ®Google Scholar
• Salehi , P. , Dabiri , M. , Zolfigol , M. A. and Bodaghi Fard , M. A. 2003 . Silica sulfuric acid: an efficient and reusable catalyst for the one‐pot synthesis of 3,4‐dihydropyrimidin‐2(1H)‐ones . Tetrahedron Lett. , 44 : 2889 [CROSSREF]
   Web of Science ®Google Scholar
• 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 [CROSSREF]
   Web of Science ®Google Scholar
• Li , J. T. , Hu , J. F. and Liu , T. S. 2003 . An efficient synthesis of 3,4‐dihydropyrimidin‐2‐ones catalyzed by NH2SO3H under ultrasound irradiation . Ultrason. Sonochem. , 10 : 119 [PUBMED] [INFOTRIEVE] [CROSSREF]
   PubMed Web of Science ®Google Scholar
• Zavyalov , S. I. and Kulikova , L. B. 1992 . Trimethylchlorosilane‐DMFA, a new system for the Biginelli reaction . Khim.‐Farm. Zh. , 26 : 1655
   Google Scholar
• Sabitha , G. , Kiran Kumar Reddy , G. S. , Srinivas Reddy , Ch. and Yadav , J. S. 2003 . One‐pot synthesis of dihydropyrimidinones using iodotrimethylsilane. Facile and new improved protocol for the Biginelli reaction at room temperature . Synlett , : 838
   Google Scholar