Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 15
250
Views
19
CrossRef citations to date
0
Altmetric
Original Articles

Brønsted Acidic Ionic Liquid–Catalyzed One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones and Thiones Under Solvent-Free Conditions

, &
Pages 2200-2208 | Received 04 Nov 2009, Published online: 25 May 2011

REFERENCES

  • Kappe , C. O. Recent advances in the Biginelli dihydropyrimidine synthesis: New tricks from an old dog . Acc. Chem. Res. 2000 , 33 , 879 .
  • Kappe , C. O. Biologically active dihydropyrimidones of the Biginelli type—A literature survey . Eur. J. Med. Chem. 2000 , 35 , 1043 .
  • Kappe , C. O. One hundred years of the Biginelli dihydropyrimidine synthesis . Tetrahedron 1993 , 49 , 6937 .
  • Rovnyak , G. C. ; Kimball , S. D. ; Beyer , B. ; Cucinotta , G. ; Dimarco , D. J. ; Gougoutas , J. ; Hedberg , A. ; Malley , M. ; McCarthy , J. P. ; Zhang , R. ; Moreland , S. Calcium entry blockers and activators: Conformational and structural determinants of dihydropyrimidine calcium channel modulators . J. Med. Chem. 1995 , 38 , 119 .
  • Atwal , K. S. ; Swanson , B. N. ; Unger , S. E. ; Floyd , D. M. ; Moreland , S. ; Hedberg , A. ; O'Reilly , B. C. 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. 1991 , 34 , 806 .
  • 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 .
  • Bruce , M. A. ; Pointdexter , G. S. ; Johnson , G. PCT Int. Appl . WO Patent 9,833,791 , 1998 .
  • (a) Patil , A. D. ; Kumar , N. V. ; Kokke , W. C. ; Bean , M. F. ; Freyer , A. J. ; Debrossi , C. ; Mai , S. ; Truneh , A. ; Faulkner , D. J. ; Carte , B. ; Breen , A. L. ; Hertzberg , R. P. ; Johnson , R. K. ; Westley , J. W. ; Potts , B. C. M. Novel alkaloids from the sponge Batzella sp.: Inhibitors of HIV gp120-human CD4 binding . J. Org. Chem. 1995 , 60 , 1182 ; (b) Snider , B. B. ; Chen , J. ; Patil , A. D. ; Freyer , A. Synthesis of the tricyclic portions of batzelladines A, B, and D: Revision of the stereochemistry of batzelladines A and D . Tetrahedron Lett. 1996 , 37 , 6977 .
  • (a) Manhas , M. S. ; Ganguly , S. N. ; Mukherjee , S. ; Jain , A. K. ; Bose , A. K. Microwave-initiated reactions: Pechmann coumarin synthesis, Biginelli reaction, and acylation. Tetrahedron Lett. 2006, 47, 2423; (b) Dandia , A. ; Saha , M. ; Taneja , H. Synthesis of fluorinated ethyl 4-aryl-6-methyl-1,2,3,4-tetrahydropyrimidin-2-one/thione-5-carboxylates under microwave irradiation. J. Fluorine Chem. 1998, 90, 17.
  • Liu , C. ; Wang , J. ; Li , Y. One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-(thio)ones using strontium(II) nitrate as a catalyst . J. Mol. Catal. A: Chem. 2006 , 258 , 367 .
  • (a) Legeay , J. C. ; Eynde , J. J. V. ; Bazureau , J. P. A new approach to N-3 functionalized 3,4-dihydropyrimidine-2(1H)-ones with 1,2,4-oxadiazole group as amide isostere via ionic liquid-phase technology . Tetrahedron Lett. 2007 , 48 , 1063 ; (b) Desai , B. ; Dallinger , D. ; Kappe , C. O. Microwave-assisted solution-phase synthesis of dihydropyrimidine C5 amides and esters . Tetrahedron 2006 , 62 , 4651 .
  • Hassani , Z. ; Islami , M. R. ; Kalantari , M. An efficient one-pot synthesis of octahydroquinazolinone derivatives using catalytic amount of H2SO4 in water . Bioorg. Med. Chem. Lett. 2006 , 16 , 4479 .
  • Fu , N. Y. ; Yuan , Y. F. ; Cao , Z. ; Wang , S. W. ; Wang , J. T. ; Peppe , C. Indium(III) bromide–catalyzed preparation of dihydropyrimidinones: Improved protocol conditions for the Biginelli reaction . Tetrahedron 2002 , 58 , 4801 .
  • Bhosale , R. S. ; Bhosale , S. V. ; Bhosale , S. V. ; Wang , T. ; Zubaidha , P. K. An efficient, high-yield protocol for the one-pot synthesis of dihydropyrimidin-2(1H)-ones catalyzed by iodine . Tetrahedron Lett. 2004 , 45 , 9111 .
  • Reddy , C. V. ; Mahesh , M. ; Raju , P. V. K. ; Babu , T. R. ; Reddy , V. V. N. Zirconium(IV) chloride–catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones . Tetrahedron Lett. 2002 , 43 , 2657 .
  • Maiti , G. ; Kundu , P. ; Guin , C. One-pot synthesis of dihydropyrimidinones catalysed by lithium bromide: An improved procedure for the Biginelli reaction . Tetrahedron Lett. 2003 , 44 , 2757 .
  • Bose , A. K. ; Manhas , M. S. ; Pednekar , S. ; Dang , H. ; He , W. ; Mandadi , A. Large-scale Biginelli reaction via water-based biphasic media: A green chemistry strategy . Tetrahedron Lett. 2005 , 46 , 1901 .
  • Chen , W.-Y. ; Qin , S. ; Jin , J. R. HBF4-catalyzed Biginelli reaction: One-pot synthesis of dihydropyrimidin-2(1H)-ones under solvent-free conditions . Catal. Commun. 2007 , 8 , 123 .
  • Ahmed , N. ; Lier , J. E. TaBr5-catalyzed Biginelli reaction: One-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones under solvent-free conditions . Tetrahedron Lett. 2007 , 48 , 5407 .
  • Shirini , F. ; Zolfigol , M. A. ; Abri , A. Fe(HSO4)3 as an efficient catalyst for the preparation of 3,4-dihydropyrimidin-2(1H)-ones in solution and under solvent-free conditions . J. Iran. Chem. Soc. 2008 , 5 , 96 .
  • Paraskar , A. S. ; Dewkar , G. K. ; Sudalai , A. Cu(OTf)2: A reusable catalyst for high-yield synthesis of 3,4-dihydropyrimidin-2(1H)-ones . Tetrahedron Lett. 2003 , 44 , 3305 .
  • Zumpe , F. L. ; Flub , M. ; Schmitz , K. ; Lender , A. Propane phosphonic acid anhydride: A new promoter for the one-pot Biginelli synthesis of 3,4-dihydropyrimidin-2(1H)-ones . Tetrahedron Lett. 2007 , 48 , 1421 .
  • Shaabani , A. ; Bazgir , A. ; Teimouri , F. Ammonium chloride–catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones under solvent-free conditions . Tetrahedron Lett. 2003 , 44 , 875 .
  • Singh , K. ; Arora , D. ; Singh , S. Dowex-promoted general synthesis of N,N′-disubstituted-4-aryl-3,4-dihydropyrimidinones using a solvent-free Biginelli condensation protocol . Tetrahedron Lett. 2006 , 47 , 4205 .
  • Rafiee , E. ; Jafari , H. A practical and green approach towards synthesis of dihydropyrimidinones: Using heteropoly acids as efficient catalysts . Bioorg. Med. Chem. Lett. 2006 , 16 , 2463 .
  • Salehi , P. ; Dabiri , M. ; Zolfigol , M. A. ; Bodaghi , M. A. Silica sulfuric acid: An efficient and reusable catalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Tetrahedron Lett. 2003, 44, 2889.
  • Chitra , S. ; Pandiarajan , K. Calcium fluoride: An efficient and reusable catalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones and their corresponding 2(1H)thione: An improved high-yielding protocol for the Biginelli reaction . Tetrahedron Lett. 2009 , 50 , 2222 .
  • Debache , A. ; Amimour , M. ; Belfaitah , A. ; Rhouati , S. ; Carboni , B. A one-pot Biginelli synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones catalyzed by triphenylphosphine as Lewis base . Tetrahedron Lett. 2008 , 49 , 6119 .
  • Suzuki , I. ; Iwata , Y. ; Takeda , K. Biginelli reactions catalyzed by hydrazine-type organocatalyst . Tetrahedron Lett. 2008 , 49 , 3238 .
  • Wilkes , J. S. Properties of ionic liquid solvents for catalysis . J. Mol. Catal. A: Chem. 2004 , 214 , 11 .
  • Hajipour , A. R. ; Khazdooz , L. ; Ruoho , A. E. Brønsted acidic ionic liquid as an efficient catalyst for chemoselective synthesis of 1,1-diacetates under solvent-free conditions . Catal. Commun. 2008 , 9 , 89 .
  • Mayer , T. U. ; Kapoor , T. M. ; Haggarty , S. ; 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 .
  • Zhao , D. ; Liao , Y. ; Zhang , Z. Toxicity of ionic liquids . Clean—Soil, Air, Water 2007 , 35 , 42 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.