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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 6
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Original Articles

Glycerin and CeCl3 · 7H2O: A New and Efficient Recyclable Reaction Medium for the Synthesis of Quinoxalines

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Pages 883-892 | Received 17 May 2010, Published online: 11 Nov 2011

REFERENCES

  • Jaso , A. ; Zarranz , B. ; Aldana , I. ; Monge , A. Synthesis of new quinoxalines-2-carb oxylate-1,4-dioxide derivatives as anti-Mycrobacterium tuberculosis agents . J. Med. Chem. 2005 , 48 , 2019 – 2025 .
  • Toshima , K. ; Ozawa , T. ; Kimura , T. ; Matsumara , S. The significant effect of the carbohydrate structures on the DNA photocleavage of the quinoxaline-carbohydrate-hybrids . Bioorg. Med. Chem. Lett. 2004 , 14 , 2777 – 2779 .
  • Sarges , R. ; Howard , H. R. ; Browne , R. G. ; Lebel , L. A. ; Seymour , P. A. 4-Amino [1,2,4]triazolo [4,3a]quinoxalines: A novel class of potent adrenosine receptor antagonists and potential rapid-onset antidepressants . J. Med. Chem. 1990 , 33 , 2240 – 2254 .
  • 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 – 6348 .
  • Driller , K. M. ; Libnow , S. ; Hein , M. ; Harms , M. ; Wende , K. ; Lalk , M. ; Michalik , D. ; Reinke , H. ; Langer , P. Synthesis of 6H-indolo[2,3b] quinoxaline-N-glycosides and their cytotoxic activity against human ceratinocytes (HaCaT) . Org. Biomol. Chem. 2008 , 6 , 4218 – 4223 .
  • Kowalski , J. A. ; Leonard , S. F. ; Lee, Jr , G. E. Diverse-2-carboxamide-3-amino-substituted quinoxalines: Synthesis and reactivity investigation for library generation . J. Comb. Chem. 2006 , 8 , 774 – 779 .
  • Lin , S. K. A facile synthesis of quinoxaline-2,3-diones as NMDA receptor antagonist . Molecules 1996 , 1 , 37 – 40 .
  • Ajaikumar , S. ; Pandurangan , A. Efficient synthesis of quinoxaline derivative over ZrO2/MxOy (M˭Al, Ga, In, and La) mixed metal oxides supported on MCM-41 mesoporous molecular sieves . Appl. Catal. A. 2009 , 357 , 184 – 192 .
  • Antoniotti , S. ; Dunach , E. Direct and catalytic synthesis of quinoxaline derivatives from epoxides and ene-1,2-diamines . Tetrahedron Lett. 2002 , 43 , 3971 – 3973 .
  • Das , B. ; Lu , K. V. ; Suneel , K. ; Majhi , A. An efficient and convenient protocol for the synthesis of quinoxalines and dihydropyrazines via cyclization–oxidation process using HClO4-SiO2 as a heterogeneous recyclable catalyst . Tetrahedron Lett. 2007 , 48 , 5371 – 5374 .
  • Sundaram , G. S. M. ; Singh , B. ; Venkatesh , C. ; Ila , H. ; Junjappa , H. Dipolar cyclo- addition of ethyl isocyanoacetate to 3-chloro-2-(methylthio)/2-(methylsulfonyl)-quino xalines: Highly region and chemoselective synthesis of substituted imidazo-[1,5-a]-quinoxaline-3-carboxylates . J. Org. Chem. 2007 , 72 , 5020 – 5023 .
  • Sithambaram , S. ; Ding , Y. ; Li , W. ; Shen , X. ; Gaenzler , F. ; Suib , S. L. Manganese octahedral molecular sieves–catalyzed tandem process for synthesis of quinoxalines . Green Chem. 2008 , 10 , 1029 – 1032 .
  • Haldar , P. ; Dutta , B. ; Guin , J. ; Ray , J. K. Uncatalyzed condensation between aryl-1,2-diamines and diethyl bromomalonates: A one-pot access to substituted ethyl 3-hydroxyquinoxaline-2-carboxylates . Tetrahedron Lett. 2007 , 48 , 5855 – 5857 .
  • Yan , L. ; Liu , F. W. ; Dai , G. F. ; Liu , H. M. An efficient synthesis of quinoxaline derivatives from 4-chloro-4-deoxy-α-d-galactose and their cytotoxic activities. Bioorg. Med. Chem. Lett. 2007 , 17 , 609 – 612 .
  • Cho , C. S. ; Oh , S. G. Copper-catalyzed oxidative cyclization of α-hydroxy ketones with o-phenylenediamines leading to quinoxalines . J. Mol. Catal. A: Chem. 2007 , 276 , 205 – 210 .
  • Yadav , J. S. ; Reddy , B. V. S. ; Rao , Y. G. ; Narsaiah , A. V. First example of Cu(OTf)2-catalyzed synthesis of quinoxalines from α-diazoketones and aryl-1,2-diamines . Chem. Lett. 2008 , 348 – 349 .
  • Heravi , M. M. ; Teheri , S. ; Bakhtiari , K. ; Oskooie , H. A. On water: A practical and efficient synthesis of quinoxaline derivatives catalyzed by CuSO4 · 5H2O. Catal. Commun. 2007, 8, 211–214.
  • Nasar , M. K. ; Kumar , R. R. ; Perumal , S. Three-component tandem reactions of (2-arylsulfanyl-3-aryl-2-oxiranyl) (aryl) methanones and o-phenylenediamine: Formation of quinoxalines . Tetrahedron Lett. 2007 , 48 , 2155 – 2158 .
  • Staszewska , A. ; Stefanowicz , P. ; Szewezuk , Z. Direct solid-phase synthesis of quinoxaline-containing peptides . Tetrahedron Lett. 2005 , 46 , 5525 – 5528 .
  • 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 – 7186 .
  • Cho , C. S. ; Ren , W. X. ; Shim , S. C. Ketones as a new synthon for quinoxaline synthesis . Tetrahedron Lett. 2007 , 48 , 4665 – 4667 .
  • Neochoritis , C. ; Stephanatou , J. S. ; Tsoleridis , C. A. Heterocyclizations via TosMIC-based multicomponent reactions: A new approach to one-pot facile synthesis of substituted quinoxaline derivatives . Synlett 2009 , 0 , 302 – 305 .
  • Cai , J. J. ; Zou , J. P. ; Pan , X. Q. ; Zhang , W. Gallium(III) triflate–catalyzed synthesis of quinoxaline derivatives . Tetrahedron Lett. 2008 , 49 , 7386 – 7390 .
  • Srinivas , C. ; Kumar , C. N. S. S. P. ; Rao , V. J. ; Palaniappan , S. Efficient, convenient, and reusable polyaniline-sulfate salt catalyst for the synthesis of quinoxaline derivatives . J. Mol. Catal. A: Chem. 2007 , 265 , 227 – 230 .
  • 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 quioxalines and heterocyclic pyrazines . Tetrahedron Lett. 2004 , 45 , 4873 – 4876 .
  • Heravi , M. M. ; Baghernejad , B. ; Oskooie , H. A. A novel three-component reaction for the synthesis of N-cyclohexyl-3-aryl-quinoxaline-2-amines . Tetrahedron Lett. 2009 , 50 , 767 – 769 .
  • Mateu , M. ; Capilla , A. S. ; Harrak , Y. ; Pujol , M. D. Synthesis of 6,7-ethylene dioxyquinoxalines and pyrido-[2,3-b]-pyrazines as intermediates in the preparation of antineoplastic agents . Tetrahedron 2002 , 58 , 5241 – 5250 .
  • Yadav , J. S. ; Reddy , B. V. S. ; Premalatha , K. ; Shankar , K. S. Bismuth(III)-catalyzed rapid synthesis of 2,3-disubstituted quinoxalines in water . Synthesis 2008 , 3787 – 3792 .
  • Hui , X. ; Desrivot , J. ; Bories , C. ; Loiseau , P. M. ; Franck , X. ; Hocquemiller , R. ; Figadére , B. Synthesis and antiprotozoal activity of some new substituted quinoxalines . Bioorg. Med. Chem. Lett. 2006 , 16 , 815 – 820 .
  • Rong , F. ; Chow , S. ; Yan , S. ; Larson , G. ; Hong , Z. ; Wu , J. Structure–activity relationship (SAR) studies of quinoxalines as novel HCV NS5B RNA-dependent RNA polymerrase inhibitor . Bioorg. Med. Chem. Lett. 2007 , 17 , 1663 – 1666 .
  • Robinson , R. S. ; Taylor , R. J. K. Quinoxaline synthesis from α-hydroxy ketones via a tandem oxidation process using catalysed aerobic oxidation . Synlett 2005 , 1003 – 1005 .
  • Silveira , C. C. ; Mendes , S. R. ; Libero , F. M. ; Lenardo , E. J. ; Perin , G. Glycerin and CeCl3 · 7H2O: A new and efficient recyclable medium for the synthesis of bis(indolyl) methanes . Tetrahedron Lett. 2009 , 50 , 6060 – 6063 .
  • Narsaiah , A. V. ; Nagaiah , B. Glycerine–CeCl3 · 7H2O: An efficient recyclable reaction medium for the synthesis of Hantzsch pyridines . Asian J. Chem. 2010 , 22 , 8099 – 8106 .

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