Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 15
322
Views
32
CrossRef citations to date
0
Altmetric
Original Articles

Brønsted Acidic Ionic Liquid as an Efficient and Reusable Catalyst for One-Pot, Three-Component Synthesis of Pyrimidinone Derivatives via Biginelli-Type Reaction Under Solvent-Free Conditions

, , &
Pages 2226-2233 | Received 10 Feb 2010, Published online: 25 May 2011

REFERENCES

  • Domling , A. ; Ugi , I. Multicomponent reactions with isocyanides . Angew. Chem. Int. Ed. 2000 , 39 , 3168 .
  • Ramon , D. J. ; Yus , M. Neue Entwicklungen in der asymmetrischen Mehrkomponenten-Reaktion . Angew. Chem. 2005 , 117 , 1628 .
  • Simon , C. ; Constantieux , T. ; Rodriguez , J. Utilisation of 1,3-dicarbonyl derivatives in multicomponent reactions . Eur. J. Org. Chem. 2004 , 4957 .
  • Ulaczyk-Lesanko , A. ; Hall , D. G. Wanted: New multicomponent reactions for generating libraries of polycyclic natural products . Curr. Opin. Chem. Biol. 2005 , 9 , 266 .
  • Atwal , K. S. ; Rovnyak , G. C. ; O'Reilly , B. C. ; Schwartz , J. Substituted 1,4-Dihydropyrimidines, 3: Synthesis of selectively functionalized 2-hetero-l,4-dihydropyrimidines . J. Org. Chem. 1989 , 54 , 5898 .
  • 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 .
  • El-Subbagh , H. I. ; Abu-Zaid , S. M. ; Mahran , M. A. ; Badria , F. A. ; Al-Obaid , A. M. Synthesis and biological evaluation of certain α,β-unsaturated ketones and their corresponding fused pyridines as antiviral and cytotoxic agents . J. Med. Chem. 2000 , 43 , 2915 .
  • Ali , M. I. ; El-Fotooh , A. ; Hammam , G. Reactions with (arylmethylene)cycloalkanones, 1: 2,6-Bis(arylmethylene)cyclohexanones . J. Chem. Eng. Data 1978 , 23 , 351 .
  • Ali , M. I. ; El-Kaschef , M. A. F. ; El-Fotooh , A. ; Hammam , G. ; Khallaf , S. A. Reactions with (arylmethylene)cycloalkanones, 2: Synthesis of 10-(arylmethylene)hexahydrocyclohepteno[1,2-d]thiazolo[3,2-a]pyrimidin-3-one derivatives of probable anticancer activity. J. Chem. Eng. Data 1979, 24, 377.
  • Ali , M. I. ; El-Fotooh , A. ; Hammam , G. ; Youssef , N. M. Reactions with (arylmethylene)cycloalkanones, 3: Synthesis of 11-(arylmethylene)octahydrocycloocta[d]thiazolo[3,2-a]pyrimidin-3-one derivatives of expected biological activity . J. Chem. Eng. Data 1981 , 26 , 214 .
  • Elgemeie , G. E. H. ; Attia , A. M. E. ; Alkabai , S. S. Nucleic acid components and their analogues: New synthesis of bicyclic thiopyrimidine nucleosides . Nucleos. Nucleot. Nucl. 2000 , 19 , 723 .
  • Zhu , Y. ; Huang , S. ; Pan , Y. Chemoselective multicomponent Biginelli-type condensations of cycloalkanones, urea or thiourea, and aldehydes . Eur. J. Org. Chem. 2005 , 2354 .
  • Zhang , H. ; Zhou , Z. ; Yao , Z. ; Xu , F. ; Shen , Q. Efficient synthesis of pyrimidinone derivatives by ytterbium chloride catalyzed Biginelli-type reaction under solvent-free conditions . Tetrahedron Lett. 2009 , 50 , 1622 .
  • Sahoo , S. ; Joseph , T. ; Halligudi , S. B. Mannich reaction in Brønsted acidic ionic liquid: A facile synthesis of β-amino carbonyl compounds . J. Mol. Catal. A: Chem. 2006 , 244 , 179 .
  • Forbes , D. C. ; Weaver , K. J. Brønsted acidic ionic liquids: The dependence on water of the Fischer esterification of acetic acid and ethanol . J. Mol. Catal. A: Chem. 2004 , 214 , 129 .
  • Welton , T. Room-temperature ionic liquids: Solvents for synthesis and catalysis . Chem. Rev. 1999 , 99 , 2071 .
  • Wasserscheid , P. ; Keim , W. Ionic liquids—new “Solutions” for transition metal catalysis . Angew. Chem. Int. Ed. 2000 , 39 , 3773 .
  • Wilkes , J. S. Properties of ionic liquid solvents for catalysis . J. Mol. Catal. A: Chem. 2004 , 214 , 11 .
  • Cole , A. C. ; Jensen , J. L. ; Ntai , I. ; Tran , K. L. T. ; Weaver , K. J. ; Forbes , D. C.; Davis Jr. , J. H. Novel Brønsted acidic ionic liquids and their use as dual solvent−catalysts . J. Am. Chem. Soc. 2002 , 124 , 5962 .
  • Fang , D. ; Shi , Q.-R. ; Cheng , J. ; Gong , K. ; Liu , Z.-L. Regioselective mononitration of aromatic compounds using Brønsted acidic ionic liquids as recoverable catalysts . Appl. Catal. A: Gen. 2008 , 345 , 158 .
  • Gui , J. ; Cong , X. ; Liu , D. ; Zhang , X. ; Hu , Z. ; Sun , Z. Novel Brønsted acidic ionic liquid as efficient and reusable catalyst system for esterification . Catal. Commun. 2004 , 5 , 473 .
  • Liu , X. ; Liu , M. ; Guo , X. ; Zhou , J. SO3H-functionalized ionic liquids for selective alkylation of m-cresol with tert-butanol . Catal. Commun. 2008 , 9 , 1 .
  • Hajipour , A. R. ; Ghayeb , Y. ; Sheikhan , N. ; Ruoho , A. E. Brønsted acidic ionic liquid as an efficient and reusable catalyst for one-pot synthesis of 1-amidoalkyl 2-naphthols under solvent-free conditions . Tetrahedron Lett. 2009 , 50 , 5649 .
  • Hajipour , A. R. ; Zarei , A. ; Khazdooz , L. ; Mirjalili , B. B. F. ; Sheikhan , N. ; Zahmatkesh , S. ; Ruoho , A. E. Silica sulfuric acid as an efficient heterogeneous catalyst for the synthesis of 1,1-Diacetates under solvent-free conditions . Synthesis 2005 , 20 , 3644 .
  • Hajipour , A. R. ; Mirjalili , B. B. F. ; Zarei , A. ; Khazdooz , L. ; Ruoho , A. E. A novel method for sulfonation of aromatic rings with silica sulfuric acid . Tetrahedron Lett. 2004 , 45 , 6607 .

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.