Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 21
275
Views
46
CrossRef citations to date
0
Altmetric
Original Articles

Efficient Synthesis of Quinoxalines in the Ionic Liquid 1-n-Butylimidazolium Tetrafluoroborate ([Hbim]BF4) at Ambient Temperature

, &
Pages 3601-3612 | Received 15 Feb 2008, Published online: 14 Oct 2008

REFERENCES

  • Seitz , L. E. ; Suling , W. J. ; Reynolds , R. C. Synthesis and antimycobacterial activity of pyrazine and quinoxaline derivatives . J. Med. Chem. 2002 , 45 , 5604 .
  • (a) Hazeldine , S. T. ; Polin , L. ; Kushner , J. ; Paluch , J. ; White , K. ; Edelstein , M. ; Palomino , E. ; Corbett , T. H. ; Horwitz , J. P. Design, synthesis, and biological evaluation of analogues of the antitumor agent, 2-{4-[(7-chloro-2-quinoxalinyl)oxy]phenoxy}propionic acid (XK469) . J. Med. Chem. 2001 , 44 , 1758 ; (b) Hazeldine , S. T. ; Polin , L. ; Kushner , J. ; White , K. ; Bouregeois , N. M. ; Crantz , B. ; Palomino , E. ; Corbett , T. H. ; Horwitz , J. P. Synthesis and biological evaluation of some bioisosteres and congeners of the antitumor agent, 2-{4-[(7-Chloro-2-quinoxalinyl)oxy]phenoxy}propionic acid (XK469) . J. Med. Chem. 2002 , 45 , 3130 .
  • Dell , A. ; William , D. H. ; Morris , H. R. ; Smith , G. A. ; Feeney , J. ; Roberts , G. C. K. Structure revision of the antibiotic echinomycin . J. Am. Chem. Soc. 1975 , 97 , 2497 .
  • Gazit , A. ; App , H. ; McMahon , G. ; Chen , J. ; Levitzki , A. ; Bohmer , F. D. Tyrphostins 5: Potent inhibitors of platelet-derived growth factor receptor tyrosine kinase: Structure–activity relationships in quinoxalines, quinolines, and indole tyrphostins . J. Med. Chem. 1996 , 39 , 2170 .
  • Sehlstedt , U. ; Aich , P. ; Bergman , J. ; Vallberg , H. ; Norden , B. ; Graslund , A. Interactions of the antiviral quinoxaline derivative 9-OH-B220 {2,3-dimethyl-6-(dimethylaminoethyl)-9-hydroxy-6H-indolo-[2,3-b]quinoxaline} with duplex and triplex forms of synthetic DNA and RNA . J. Mol. Biol. 1998 , 278 , 31 .
  • Dailey , S. ; Feast , J. W. ; Peace , R. J. ; Till , S. ; Sage , I. C. ; Wood , E. L. Synthesis and device characterisation of side-chain polymer electron transport materials for organic semiconductor applications . J. Mat. Chem. 2001 , 11 , 2238 .
  • O'Brien , D. ; Weaver , M. S. ; Lidzey , D. G. ; Bradley , D. D. C. Use of poly(phenyl quinoxaline) as an electron transport material in polymer light-emitting diodes . Appl. Phys. Lett. 1996 , 69 , 881 .
  • Justin Thomas , K. R. ; Marappan , V. ; Jiann , T. L. ; Chang-Hao , C. ; Yu-ai , T. Chromophore-labeled quinoxaline derivatives as efficient electroluminescent materials . Chem. Mater. 2005 , 17 , 1860 .
  • Jonathan , L. S. ; Hiromitsu , M. ; Toshihisa , M. ; Vincent , M. L. ; Hiroyuki , F. Quinoxaline-oligopyrroles: Improved pyrrole-based anion receptors . Chem. Commun. 2002 , 862 .
  • (a) Jonathan , L. S. ; Hiromitsu , M. ; Toshihisa , M. ; Vincent , M. L. ; Hiroyuki , F. Quinoxaline-bridged porphyrinoids . J. Am. Chem. Soc. 2002 , 124 , 13474 ; (b) Peter , P. C. ; Gang , Z. ; Grace , A. M. ; Carlos , H. ; Linda , M. G. T. Quinoxaline excision: A novel approach to tri- and diquinoxaline cavitands . Org. Lett. 2004 , 6 , 333 .
  • Sascha , O. ; Rudiger , F. Quinoxalinodehydroannulenes: A novel class of carbon-rich materials . Synlett 2004 , 1509 .
  • (a) Kazunobu , T. ; Ryusuke , T. ; Tomohiro , O. ; Shuichi , M. Molecular design and evaluation of quinoxaline-carbohydrate hybrids as novel and efficient photo-induced GG-selective DNA cleaving agents . Chem. Commun. 2002 , 212 ; (b) Hegedus , L. S. ; Marc , M. G. ; Jory , J. W. ; Joseph , P. B. Synthesis of 5,12-dioxocyclam nickel(II) complexes having quinoxaline substituents at the 6 and 13 positions as potential DNA bis-intercalating and cleaving agents . J. Org. Chem. 2003 , 68 , 4179 .
  • Brown , D. J. Quinoxalines: Supplement II. In The Chemistry of Heterocyclic Compounds ; E. C. Taylor , P. Wipf (Eds.); John Wiley & Sons : NJ , 2004.
  • Antoniotti , S. ; Donach , E. Direct and catalytic synthesis of quinoxaline derivatives from epoxides and ene-1,2-diamines . Tetrahedron Lett. 2002 , 43 , 3971 .
  • Wu , Z. ; Ede , N. J. Solid-phase synthesis of quinoxalines on SynPhase lanterns . Tetrahedron Lett. 2001 , 42 , 8115 .
  • Xekoukoulotakis , N. P. ; Hadjiantonious , M. C. P. ; Maroulis , A. J. Synthesis of quinoxalines by cyclization of α-arylimino oximes of α-dicarbonyl compounds . Tetrahedron Lett. 2000 , 41 , 10299 .
  • Zhao , Z. ; Wisnoski , D. D. ; Wolkenberg , S. E. ; Leister , W. H. ; Wang , Y. ; Lindsley , C. W. General microwave-assisted protocols for the expedient synthesis of quinoxalines and heterocyclic pyrazines . Tetrahedron Lett. 2004 , 45 , 4873 .
  • Bhosale , R. S. ; Sarda , S. R. ; Ardhapure , S. S. ; Jadhav , W. N. ; Bhusare , S. R. ; Pawar , R. P. An efficient protocol for the synthesis of quinoxaline derivatives at room temperature using molecular iodine as the catalyst . Tetrahedron Lett. 2005 , 46 , 7183 .
  • More , S. V. ; Sastry , M. N. V. ; Wang , C.-C. ; Yao , C.-F. Molecular iodine: A powerful catalyst for the easy and efficient synthesis of quinoxalines . Tetrahedron Lett. 2005 , 46 , 6345 .
  • More , S. V. ; Sastry , M. N. V. ; Yao , C.-F. Cerium(IV) ammonium nitrate (CAN) as a catalyst in tap water: A simple, proficient, and green approach for the synthesis of quinoxalines . Green Chem. 2006 , 8 , 91 .
  • (a) Taheri , S. ; Bakhtiari , K. ; Oskooie , H. A. On water: A practical and efficient synthesis of quinoxaline derivatives catalyzed by CuSO4-5H2O . Catal. Commun. 2007 , 8 , 211 ; (b) Heravi , M. M. ; Tehrani , M. H. ; Bakhtiari , K. ; Oskooie , H. A. Zn[(L)proline]: A powerful catalyst for the very fast synthesis of quinoxaline derivatives at room temperature . Catal. Commun. 2007 , 8 , 1341 .
  • (a) Welton , T. Solvents for synthesis and catalysis . Chem. Rev. 1999 , 99 , 2071 ; (b) Wasserscheid , P. ; Keim , W. Ionic liquids—New solutions for transition metal catalysis . Angew. Chem., Int. Ed. Eng. 2000 , 39 , 3772 ; (c) Sheldon , R. Catalytic reactions in ionic liquids . Chem. Commun. 2001 , 2399 ; (d) Wilkes , J. S. A short history of ionic liquids—From molten salts to neoteric solvents . Green Chem. 2002 , 4 , 73 ; (e) Jain , N. ; Kumar , A. ; Chauhan , S. ; Chauhan , S. M. S. Chemical and biochemical transformations in ionic liquids . Tetrahedron 2005 , 61 , 1015 .
  • (a) Palimkar , S. S. ; Siddiqui , S. A. ; Daniel , T. ; Lahoti , R. J. ; Srinivasan , K. V. Ionic liquid–promoted regiospecific friedlander annulation: Novel synthesis of quinolines and fused polycyclic quinolines . J. Org. Chem. 2003 , 68 , 9371 ; (b) Potewar , T. M. ; Daniel , T. ; Lahoti , R. J. ; Srinivasan , K. V. Efficient synthesis of 3,5,6-trisubstituted-1,2,4-triazines in the Brønsted acidic ionic liquid, 1-n-butylimidazolium tetrafluoroborate ([Hbim]BF4) . Synth. Commun. 2007 , 37 , 261 ; (c) Potewar , T. M. ; Siddiqui , S. A. ; Lahoti , R. J. ; Srinivasan , K. V. Efficient and rapid synthesis of 1-substituted-1H-1,2,3,4-tetrazoles in the acidic ionic liquid 1-n-butylimidazolium tetrafluoroborate . Tetrahedron Lett. 2007 , 48 , 1721 ; (d) Potewar , T. M. ; Ingale , S. A. ; Srinivasan , K. V. Efficient synthesis of 2,4-disubstituted thiazoles using ionic liquid under ambient conditions: A practical approach towards the synthesis of fanetizole . Tetrahedron 2007 , 63 , 11066 .

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.