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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 1
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Original Articles

A Facile and Efficient One‐Pot Synthesis of Dihydropyrimidinones Catalyzed by Magnesium Bromide Under Solvent‐Free Conditions

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Pages 171-179 | Received 27 May 2003, Published online: 16 Aug 2006

References

  • Kappe , C. O. 1993 . 100 Years of the Biginelli dihydropyrimidine synthesis . Tetrahedron , 49 : 6937 references cited therein
  • Atwal , K. S. , Rovnyak , G. C. , O'Reilly , B. C. and Schwartz , J. 1989 . Substituted 1,4‐dihydropyrimidines. 3. Synthesis of selectivity functionalized 2‐hetero‐1,4‐dihydropyrimidines . J. Org. Chem. , 54 : 5898
  • Kappe , C. O. , Fabian , W. M.F. and Semones , M. A. 1997 . Conformational analysis of 4‐aryl‐dihydropyrimidine calcium channel modulators. A comparison of ab initio, semiempirical and x‐ray crystallographic studies . Tetrahedron , 53 : 2803 [CROSSREF]
  • Patil , A. D. , Kumar , N. V. , Kokke , W. C. , Bean , M. F. , Freyer , A. J. , De Brosse , C. , Mai , S. , Truneh , A. , Faulkner , D. J. , Crate , B. , Breen , A. L. , Hertzberg , R. P. , Johnson , R. K. , Westley , J. W. and Potts , B. C.M. 1995 . Novel alkaloids from the sponge Batzella sp.: inhibitors of HIV gp120‐human CD4 binding . J. Org. Chem. , 60 : 1182
  • Snider , B. B. , Chen , J. , Patil , A. D. and Freyer , A. 1996 . Synthesis of the tricyclic portions of batzelladines A, B and D. Revision of the stereochemistry of batzelladines A and D . Tetrahedron Lett. , 37 : 6977 [CROSSREF]
  • Rama Rao , A. V. , Gujar , M. K. and Vasudevan , J. 1995 . An enantiospecific synthesis of the tricyclic guanidine segmant of the anti‐HIV marine alkaloid batzelladine A . J. Chem. Soc., Chem. Commun. , : 1369 [CROSSREF]
  • Biginelli , P. 1893 . Gazz. Chim. Ital. , 23 : 360
  • Folkers , K. , Harwood , H. J. and Johnson , T. B. 1932 . Researches on pyrimidines. CXXX. Synthesis of 2‐keto‐1,2,3,4‐tetrahydropyrimidines . J. Am. Chem. Soc. , 54 : 3751
  • Wipf , P. and Cunningham , A. 1995 . A solid phase protocol of the Biginelli dihydropyrimidine synthesis suitable for combinatorial chemistry . Tetrahedron Lett. , 36 : 7819 [CROSSREF]
  • Atwal , K. S. , O'Reilly , B. C. , Gougoutas , J. Z. and Malley , M. F. 1987 . Synthesis of substituted 1,2,3,4‐tetrahydro‐6‐methyl‐2‐thioxo‐5‐pyrimidinecarboxylic acid esters . Heterocycles , 26 : 1189
  • Barluenga , J. , Tomas , M. , Rubio , V. and Gotor , V. 1979 . Simple and regioselective synthesis of N‐substituted pyrimidine‐2(1H)‐ones and ‐thiones . J. Chem. Commun. , : 675 [CROSSREF]
  • Mizuno , N. and Misono , M. 1998 . Heterogeneous catalysis . Chem. Rev. , 98 : 199 [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Hu , E. H. , Sidler , D. R. and Dolling , U. H. 1998 . Unprecedented catalytic three componenet one‐pot condensation reaction: an efficient synthesis of 5‐alkoxycarbonyl‐4‐aryl‐3,4‐dihydropyrimidin‐2(1H)‐ones . J. Org. Chem. , 63 : 3454 – 3457 . [CROSSREF]
  • Lu , J. and Ma , H. 2000 . Iron(III)‐catalyzed synthesis of dihydropyrimidinones. Improved conditions for the Biginelli reaction . Synlett. , : 63 – 64 .
  • 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 – 9078 . [CROSSREF]
  • 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‐1(1H)‐ones . Tetrahedron Lett. , 43 : 2657 – 2659 . [CROSSREF]
  • Peng , J. and Deng , Y. 2001 . Ionic liquids catalyzed Biginelli reaction under solvent‐free conditions . Tetrahedron Lett. , 42 : 5917 [CROSSREF]
  • Yadav , J. S. , Reddy , B. V.S. , Reddy , K. B. , Raj , K. S. and Prasad , K. A.R. 2001 . Ultrasound‐accelerated synthesis of 3,4‐dihydropyrimidin‐2(1H)‐ones with ceric ammonium nitrate . J. Chem. Soc., Perkin Trans. 1 , : 1939 [CROSSREF]
  • Yadav , J. S. , Reddy , B. V.S. , Reddy , E. J. and Ramalingam , T. J. 2000 . Microwave‐assisted efficient synthesis of dihydro pyrimidines: improved high yielding protocol for the Biginelli reaction . Chem. Res. (S) , : 354
  • Bigi , F. , Carloni , S. , Frullanti , B. , Magi , R. and Satori , 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]
  • 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]
  • Xue , S. , Shen , Y. C. , Li , Y. L. , Shen , X. M. and Guo , Q. X. 2002 . Synthesis of 4‐aryl‐3,4‐dihydropyrimidinones using microwave‐assisted solventless Biginelli reaction . Chinese J. Chem. , 20 : 385 – 389 .
  • Gupta , R. , Gupta , A. K. , Paul , S. and Kachroo , P. L. 1995 . Improved synthesis of some ethyl 4‐aryl‐6‐methyl‐1,2,3,4‐tetrahydropyrimidin‐2‐one/thion‐5‐carboxylates by microwave irradiation . Indian J. Chem. , 34B : 151
  • Varala , R. , Alam , M. 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. , : 67
  • Yun , M. , Changtao , Q. , Limin , W. and Min , Y. 2000 . Lanthanide triflate catalyzed Biginelli reaction. One‐pot synthesis of dihydropyrimidinones under solvent‐free conditions . J. Org. Chem. , 65 : 3864 – 3868 . [CROSSREF]
  • Kashima , C. , Takahashi , K. and Fukusaka , K. J. 1995 . The magnesium bromide induced Claisen condensation reaction of N‐acylpyrazoles . Heterocycl. Chem. , 32 : 1775 – 1778 .
  • Jui , W. H. , Chair , D. C. and Man , K. L. 1999 . Magnesium bromide promoted Barbier‐type intramolecular cyclization of halo‐substituted acetals, ketals, and orthoesters . Tetrahedron Lett. , 40 : 8647 – 8650 . [CROSSREF]
  • Matsumoto , A. and Nakamura , S. 1999 . Radical polymerization of methyl methacrylate in the presence of magnesium bromide as the Lewis acid . J. Appl. Polym. Sci. , 74 : 290 – 296 .
  • Kashima , C. , Fukusaka , K. , Takahashi , K. and Yokoyama , Y. 1999 . Diastereoselective Diels–Alder reaction of 2‐(α,β‐unsaturated)acyl‐3‐phenyl‐1‐menthopyrazoles . J. Org. Chem. , 64 : 1108 – 1114 . [CROSSREF]
  • Evans , D. A. , Downey , C. W. , Shaw , J. T. and Tedrow , J. S. 2002 . Magnesium halide‐catalyzed anti‐aldol reactions of chiral N‐acylthiazolidinethiones . Org. Lett. , 4 : 1127 – 1130 . [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Pansare , S. V. , Malusare , M. G. and Rai , A. N. 2000 . Magnesium bromide catalysed acylation of alcohols . Synth. Commun. , 30 : 2587 – 2592 .
  • Anastas , P. T. and Warner , J. C. 1998 . Green Chemistry: Theory and Practice 1 – 129 . New York : Oxford .
  • Tanaka , K. and Toda , F. 2000 . Solvent‐free organic synthesis . Chem. Rev. , 100 : 1025 [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Varma , R. S. 1999 . Solvent‐free organic syntheses: using supported reagents and microwave irradiation . Green Chem. , 1 : 43 [CROSSREF]
  • Yadav , J. S. and Mashram , H. M. 2001 . Green twist to an old theme. An eco‐friendly approach . Pure. Appl. Chem. , 73 : 199 – 203 .

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