Microwave-Promoted Synthesis of 3,4-Dihydropyrimidin-2(1H)-(thio)ones Using IL-ONO as Recyclable Base Catalyst Under Solvent-Free Conditions

REFERENCES

• Kappe , C. O. One hundred years of the Biginelli dihydropyrimidine synthesis . Tetrahedron 1993 , 49 , 6937 .
   Web of Science ®Google Scholar
• 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-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 .
   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 .
   PubMed Web of Science ®Google Scholar
• Overman , L. E. ; Rabinowitz , M. H. ; Renhowe , P. A. Enantioselective total synthesis of (−)-ptilomycalin A . J. Am. Chem. Soc. 1995 , 117 , 2657 .
   Web of Science ®Google Scholar
• Gong , K. ; Fang , D. ; Wang , H.-L. ; Zhou , X.-L. ; Liu , Z.-L. The one-pot synthesis of 14-alkyl- or aryl-14H-dibenzo[a,j]xanthenes catalyzed by task-specific ionic liquid . Dyes Pigments 2009 , 80 , 30 .
   Web of Science ®Google Scholar
• Le , Z.-G. ; Chen , Z.-C. ; Hu , Y. ; Zheng , Q.-G. [bmim]Br3 as a new reagent for regioselective monobromination of arylamines under solvent-free conditions . Synthesis 2004 , 2809 .
   Web of Science ®Google Scholar
• Yue , C. ; Mao , A. ; Wei , Y. ; Lü , M. Knoevenagel condensation reaction catalyzed by task-specific ionic liquid under solvent-free conditions . Catal. Commun. 2008 , 9 , 1571 .
   Web of Science ®Google Scholar
• Wang , L. ; Li , H. ; Li , P. Task-specific ionic liquid as base, ligand, and reaction medium for the palladium-catalyzed Heck reaction . Tetrahedron 2009 , 65 , 364 .
   Web of Science ®Google Scholar
• Macfarlane , D. R. ; Pringle , J. M. ; Johansson , K. M. ; Forsyth , S. A. ; Forsyth , M. Lewis base ionic liquids. Chem. Commun. 2006, 1905.
   PubMed Web of Science ®Google Scholar
• Welton , T. Room-temperature ionic liquids: Solvents for synthesis and catalysis . Chem. Rev. 1999 , 99 , 2071 , and references cited therein.
   PubMed Web of Science ®Google Scholar
• Suarez , P. A. Z. ; Dullius , J. E. L. ; Einloft , S. ; De Souza , R. ; Dupont , J. The use of new ionic liquids in two-phase catalytic hydrogenation reaction by rhodium complexes . Polyhedron 1996 , 15 , 1217 .
   Web of Science ®Google Scholar
• Dhar , L. ; Yadav , S. ; Patel , R. ; Rai , V. ; Vishnu , K. ; Srivastava , P. An efficient conjugate hydrothiocyanation of chalcones with a task-specific ionic liquid . Tetrahedron Lett. 2007 , 48 , 7793 .
   Web of Science ®Google Scholar
• Siyutkin , D. E. ; Kucherenko , A. S. ; Struchkova , M. I. ; Zlotin , S. G. A novel (S)-proline-modified task-specific chiral ionic liquid—An amphiphilic recoverable catalyst for direct asymmetric aldol reactions in water . Tetrahedron Lett. 2008 , 49 , 1212 .
   Web of Science ®Google Scholar
• Paun , C. ; Barklie , J. ; Goodrich , P. ; Gunaratne , H. Q. N. ; McKeown , A. ; Pârvulescu , V. I. ; Hardacre , C. Supported and liquid-phase task-specific ionic liquids for base-catalysed Knoevenagel reactions . J. Mol. Catal. A: Chem. 2007 , 269 , 64 .
   Web of Science ®Google Scholar
• Tajik , H. ; Niknam , K. ; Parsa , F. Using acidic ionic liquid 1-butyl-3-methylimidazolium hydrogen sulfate in selective nitration of phenols under mild conditions . J. Iran. Chem. Soc. 2009 , 6 , 159 .
   Web of Science ®Google Scholar
• Bhosale , R. S. ; Sarda , S. R. ; Giram , R. P. ; Raut , D. S. ; Parwe , S. P. ; Ardhapure , S. S. ; Pawar , R. P. Ionic liquid–promoted expeditious synthesis of flavones . J. Iran. Chem. Soc. 2009 , 6 , 519 .
   Web of Science ®Google Scholar
• Hajipour , A. R. ; Rafiee , F. ; Ruoho , A. E. A rapid and convenient method for the synthesis of aldoximes under microwave irradiation using in situ generated ionic liquids . J. Iran. Chem. Soc. 2010 , 7 , 114 .
   Web of Science ®Google Scholar
• Jiang , C. ; You , Q. D. An efficient and solvent-free one-pot synthesis of dihydropyrimidinones under microwave irradiation . Chin. Chem. Lett. 2007 , 18 , 647 – 650 .
   Web of Science ®Google Scholar
• Choudhary , V. R. ; Tillu , V. H. ; Narkhede , V. S. ; Borate , H. B. ; Wakharkar , R. D. Microwave-assisted solvent-free synthesis of dihydropyrimidinones by Biginelli reaction over Si-MCM-41-supported FeCl3 catalyst . Catal. Commun. 2003 , 4 , 449 .
   Web of Science ®Google Scholar
• Han , J. J. ; Xu , Y. F. ; Su , Y. P. ; She , X. G. ; Pan , X. F. Guanidine-catalyzed Henry reaction and Knoevenagel condensation . Catal. Commun. 2008 , 9 , 2077 .
   Web of Science ®Google Scholar
• Bartoli , G. ; Bosco , M. ; Carlone , A. ; Dalpozzo , R. ; Galzerano , P. ; Melchiorre , P. ; Sambri , L. Magnesium perchlorate as efficient Lewis acid for the Knoevenagel condensation between β-diketones and aldehydes . Tertrahedron Lett. 2008 , 49 , 2555 .
   Web of Science ®Google Scholar
• Reddy , B. M. ; Patil , M. K. ; Rao , K. N. ; Reddy , G. K. An easy-to-use heterogeneous promoted zirconia catalyst for Knoevenagel condensation in liquid phase under solvent-free conditions . J. Mol. Catal. A: Chem. 2006 , 258 , 302 .
   Web of Science ®Google Scholar
• Martns , L. ; Vieira , K. M. ; Rios , L. M. ; Cardoso , D. Basic-catalyzed Knoevenagel condensation by FAU zeolites exchanged with alkylammonium cations . Catal. Today 2008 , 133 , 706 .
   Web of Science ®Google Scholar
• Green , B. ; Grane , R. I. ; Khaidem , I. S. ; Leighton , R. S. ; Newaz , S. S. ; Smyser , T. E. Synthesis of steroidal 16,17-fused unsaturated. δ-lactones . J. Org. Chem. 1985 , 50 , 640 .
   Web of Science ®Google Scholar
• Narsaiah , A. V. ; Nagaiah , K. An efficient knoevenagel condensation catalyzed by LaCl3 · 7H2O in heterogeneous medium . Synth. Commun. 2003 , 33 , 3825 .
   Web of Science ®Google Scholar
• Attanasi , O. ; Fillippone , P. ; Mei , A. Effect of metal ions in organic synthesis, part 16: Knoevenagel condensations of aldehydes and tosylhydrazones with 2,4-pentanedione by copper(II) chloride-catalyzed reaction . Synth. Commun. 1983 , 13 , 1203 .
   Web of Science ®Google Scholar
• Mogilaiah , K. ; Srinivas , K. ; Sudhakar , G. R. Microwave-induced ecofriendly solvent-free Biginelli reaction catalyzed by calcium chloride . Ind. J. Chem., Sec. B 2004 , 43B , 2018 .
   Google Scholar
• Valizadeh , H. ; Shockravi , A. Imidazolium-based phosphinite ionic liquid as reusable catalyst and solvent for one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-(thio)ones. Heteroatom Chem. 2009, 20, 284.
   Web of Science ®Google Scholar
• Valizadeh , H. ; Gholipour , H. Imidazolium-based phosphinite ionic liquid (IL-OPPh2) as reusable catalyst and solvent for the Knoevenagel condensation reaction . Synth. Commun. 2010 , 40 , 1477 .
   Web of Science ®Google Scholar
• Valizadeh , H. Efficient combination of task-specific ionic liquid and microwave dielectric heating applied to synthesis of a large variety of nitrones . Heteroatom Chem. 2010 , 21 , 78 .
   Web of Science ®Google Scholar
• Valizadeh , H. ; Shockravi , A. Task-specific ionic liquid as reagent and reaction medium for the one-pot Horner–Wadsworth–Emmons-type reaction under microwave irradiation . Synth. Commun. 2009 , 39 , 4341 .
   Web of Science ®Google Scholar
• Valizadeh , H. ; Heravi , M. M. ; Amiri , M. Unexpected synthesis of N-methylbenzo[d]isoxazolium hydroxides under microwave irradiation conditions . Mol. Divers. 2010 , 14 , 575 .
   PubMed Web of Science ®Google Scholar
• Su , W. ; Li , J. ; Zheng , Z. ; Shen , Y. One-pot synthesis of dihydropyrimidiones catalyzed by strontium(II) triflate under solvent-free conditions . Tetrahedron Lett. 2005 , 46 , 6037 .
   Web of Science ®Google Scholar
• Sun , Q. ; Wang , Y. ; Ge , Z. ; Cheng , T. ; Li , R. A highly efficient solvent-free synthesis of dihydropyrimidinones catalyzed by zinc chloride . Synthesis 2004 , 1047 .
   Web of Science ®Google Scholar
• Heravi , M. M. ; Bakhtiari , K. ; Bamoharram , F. F. 12-Molybdophosphoric acid: A recyclable catalyst for the synthesis of Biginelli-type 3,4-dihydropyrimidine-2(1H)-ones . Catal. Commun. 2006 , 7 , 373 .
   Web of Science ®Google Scholar
• Fu , N. ; Yuan , Y. ; Cao , Z. ; Wang , S. ; Wang , J. ; Peppe , C. Indium(III) bromide–catalyzed preparation of dihydropyrimidinones: Improved protocol conditions for the Biginelli reaction . Tetrahedron 2002 , 58 , 4801 .
   Web of Science ®Google Scholar
• Zheng , R. W. ; Wang , X. X. ; Xu , H. ; Du , J. X. Brønsted acidic ionic liquid: An efficient and reusable catalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones . Synth. Commun. 2006 , 36 , 1503 .
   Web of Science ®Google Scholar
• Xue , S. ; Shen , Y. C. ; Li , Y. L. ; Shen , X. M. ; Guo , Q. X. Synthesis of 4-aryl-3,4-dihydropyrimidinones using microwave-assisted solventless Biginelli reaction . Chin. J. Chem. 2002 , 20 , 385 .
   Web of Science ®Google Scholar