Silica-Gel–Catalyzed Efficient Synthesis of Quinoxaline Derivatives Under Solvent-Free Conditions

REFERENCES

• Loriga , M. ; Piras , S. ; Sanna , P. ; Paglietti , G. Quinoxaline chemistry, part 7: 2-[Aminobenzoates]- and 2-[aminobenzoylglutamate]-quinoxalines as classical antifolate agents: Synthesis and evaluation of in vitro anticancer, anti-HIV, and antifungal activity . Farmaco 1997 , 52 , 157 .
   PubMedGoogle Scholar
• Hui , X. ; Desrivot , J. ; Bories , C. ; Loiseau , P. M. ; Frank , X. ; Hocquimiller , R. ; Figadère , B. Synthesis and antiprotozoal activity of some new synthetic substituted quinoxalines . Bioorg. Med. Chem. Lett. 2006 , 16 , 815 .
   PubMed Web of Science ®Google Scholar
• Sakata , G. ; Makino , K. ; Karasawa , Y. Recent progress in the quinoxaline chemistry: Synthesis and biological and references cited therein activity . Heterocycles 1988 , 27 , 2481 , and references cited in therein .
   Web of Science ®Google Scholar
• Lindsley , C. W. ; Zhao , Z. ; Leister , W. H. ; Robinson , R. G. ; Barnell , S. F. ; Defeozones , D. ; Jones , R. E. ; Hartman , G. D. ; Huff , J. R. ; Huber , H. E. ; Duggan , M. E. Allosteric Akt (PKB) inhibitors: Discovery and SAR of isozyme selective inhibitors . Bioorg. Med. Chem. Lett. 2005 , 15 , 761 .
   PubMed Web of Science ®Google Scholar
• Guillon , J. ; Philippe , G. ; Labaied , M. ; Sonnet , P. ; Lèger , J. M. ; Poulain , P. D. ; Bares , I. F. ; Dallemagne , P. ; Lemaitre , N. ; Pehourcq , F. ; Rochette , J. ; Sergheraert , C. ; Christian , J. Synthesis, antimalarial activity, and molecular modeling of new pyrrolo[1,2-a]quinoxalines, bispyrrolo[1,2-a]quinoxalines, bispyrido[3,2-e]pyrrolo[1,2-a]pyrazines, and bispyrrolo[1,2-a]thieno[3,2-e]pyrazines . J. Med. Chem. 2004 , 47 , 1997 .
   PubMed Web of Science ®Google Scholar
• Sarges , R. ; Howerd , H. R. ; Browne , R. C. ; Label , L. A. ; Seymour , P. A. 4-Amino[1,2,4] triazolo[4,3-a]quinoxalines: A novel class of potent adenosine receptor antagonists and potential rapid-onset antidepressants. J. Med. Chem. 1990, 33, 2240.
   PubMed Web of Science ®Google Scholar
• (a) 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 ; (b) Bailly , C. ; Echepare , S. ; Gago , F. ; Waring , M. Recognition elements that determine affinity and sequence-specific binding to DNA of 2QN, a biosynthetic bis-quinoline analogue of echinomycin . J. Anticancer Drug Des. 1999 , 15 , 291 .
   PubMed Web of Science ®Google Scholar
• (a) Dailey , S. ; Feast , J. W. ; Peace , R. J. ; Sage , I. C. ; Till , S. ; Wood , E. L. Synthesis and device characterisation of side-chain polymer electron transport materials for organic semiconductor applications . J. Mater. Chem. 2001 , 11 , 2238 . (b) 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 ; (c) Sonawane , N. D. ; Rangnekar , D. W. Synthesis and application of 2-styryl-6,7-dichlorothiazolo[4,5-b]quinoxaline-based fluorescent dyes: Part 3 . J. Heterocycl. Chem. 2002 , 39 , 303 .
   Web of Science ®Google Scholar
• Thomas , K. R. J. ; Velusamy , M. ; Lin , J. T. ; Chuen , C. H. ; Tao , Y. T. Chromophore-labeled quinoxaline derivatives as efficient electroluminescent materials . Chem. Mater. 2005 , 17 , 1860 .
   Web of Science ®Google Scholar
• Brown , D. J. Quinoxalines: Supplement II . In The Chemistry of Heterocyclic Compounds ; E. C. Taylor , P. Wipf (Eds.); John Wiley & Sons : New York , 2004 .
   Google Scholar
• 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 .
   Web of Science ®Google Scholar
• Srinivas , C. ; Kumar , C. N. S. S. P. ; Jayathirtha Rao , V. ; Palaniappan , S. Efficient, convenient, and reusable polyaniline–sulfate salt catalyst for the synthesis of quinoxaline derivatives . J. Mol. Catal. A: Chem. 2007 , 265 , 227 .
   Web of Science ®Google Scholar
• Huang , T. K. ; Wang , R. ; Shi , L. ; Lu , X. X. Montmorillonite K-10: An efficient and reusable catalyst for the synthesis of quinoxaline derivatives in water . Catal. Commun. 2008 , 9 , 1143 .
   Web of Science ®Google Scholar
• Hazarika , P. ; Gogoi , P. ; Konwar , D. Efficient and green method for the synthesis of 1,5-benzodiazepine and quinoxaline derivatives in water . Synth. Commun. 2007 , 37 , 3447 .
   Web of Science ®Google Scholar
• Heravi , M. M. ; Bakhtiari , K. ; Oskooie , H. A. ; Taheri , S. MnCl2-promoted synthesis of quinoxaline derivatives at room temperature . Heteroatom Chem. 2008 , 19 , 218 .
   Web of Science ®Google Scholar
• Heravi , M. M. ; 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 .
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• Heravi , M. M. ; Bakhtiari , K. ; Tehrani , M. H. ; Javedi , N. M. ; Oskooie , H. A. Facile synthesis of quinoxaline derivatives using o-iodoxybenzoic acid (IBX) at room temperature . Arkivoc 2006 , 16 , 16 .
   Web of Science ®Google Scholar
• (a) Cai , J. J. ; Zou , J. P. ; Pan , X. Q. ; Zhang , W. Gallium(III) triflate–catalyzed synthesis of quinoxaline derivatives . Tetrahedron Lett. 2008 , 49 , 7386 ; (b) Raju , B. C. ; Theja , N. D. ; Kumar , J. A. Efficient and inexpensive synthesis of benzimidazoles and quinoxalines . Synth. Commun. 2009 , 39 , 175 .
   Web of Science ®Google Scholar
• Antoniotti , S. ; Duńach , E. Direct and catalytic synthesis of quinoxaline derivatives from epoxides and ene-1,2 diamines. Tetrahedron Lett. 2002, 43, 3971.
   Web of Science ®Google Scholar
• Venkatesh , C. ; Singh , B. ; Mahata , P. K. ; Ila , H. ; Junjappa , H. Heteroannulation of nitroketene N,S-arylaminoacetals with POCl3: A novel highly regioselective synthesis of unsymmetrical 2,3-substituted quinoxalines . Org. Lett. 2005 , 7 , 2169 .
   PubMed Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• (a) Raw , S. A. ; Wilfred , C. D. ; Taylor , R. J. K. Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds . Org. Biomol. Chem. 2004 , 788 ; (b) Raw , S. A. ; Wilfred , C. D. ; Taylor , R. J. K. Preparation of quinoxalines, dihydropyrazines, pyrazines, and piperazines using tandem oxidation processes . Chem. Commun. 2003 , 2286 .
   PubMed Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• (a) Nandi , G. C. ; Samai , S. ; Kumar , R. ; Singh , M. S. An efficient one-pot synthesis of tetrahydrobenzo[a]xanthene-11-one and diazabenzo[a]anthracene-9,11-dione derivatives under solvent-free condition . Tetrahedron 2009 , 65 , 7129 ; (b) Samai , S. ; Nandi , G. C. ; Kumar , R. ; Singh , M. S. Multicomponent one-pot solvent-free synthesis of functionalized unsymmetrical dihydro-1H-indeno[1,2-b]pyridines . Tetrahedron Lett. 2009 , 50 , 7096 – 7098 .
   Web of Science ®Google Scholar
• Jin , Y. Z. ; Yasuda , N. ; Furuno , H. ; Inanaga , J. Organic synthesis in solid media: Silica gel as an effective and reusable medium for the selective allylation of aldehydes with tetraallyltin . Tetrahedron Lett. 2003 , 44 , 8765 .
   Web of Science ®Google Scholar
• (a) Firouzabadi , H. ; Iranpoor , N.; Jafarpour M. ; Ghaderi , A. Silica-gel-catalyzed highly selective C-S bond formation via Michael addition of thiols to α,β-unsaturated ketones under solvent-free conditions . J. Mol. Catal. A: Chem. 2006 , 249 , 98 ; (b) Ramazani , A. ; Souldozi , A. Silica-gel-catalyzed conversion of dialkyl 2-(2-hydroxy-1-naphthyl)-3-(1,1,1-triphenyl-λ5-phosphanylidene)succinates to alkyl 3-oxo-3H-benzo[f]chromene-1-carboxylates in solvent-free conditions . Phosphorus, Sulphur Silicon Relat. Elem. 2003 , 178 , 1329 .
   Web of Science ®Google Scholar
• (a) Chari , M. A. ; Shobha , D. ; Mukkanti , K. Silica gel/FeCl3: An efficient and recyclable heterogenous catalyst for one-step synthesis of 4(3H)-quinazolinones under solvent-free conditions . Catal. Commun. 2006 , 7 , 787 ; (b) Sadeghi , B. ; Mirjalili , B. B. F. ; Hashemi , M. M. BF3 · SiO2: An efficient reagent system for the one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles . Tetrahedron Lett. 2008 , 49 , 2575 ; (c) Das , B. ; Laxminarayana , K. ; Krishnaiah , M. ; Srinivas , Y. An efficient and convenient protocol for the synthesis of novel 12-aryl- or 12-alkyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one derivatives . Synlett 2007 , 3107 ; (d) Oskooie , H. A. ; Heravi , M. M. ; Sadnia , A. ; Jannati , F. ; Behbahavi , F. K. H2SO4/silica gel: Highly efficient catalyst for the synthesis of α-aminonitriles using trimethysilyl cyanide . Monatsh. Chem. 2008 , 139 , 27 .
   Web of Science ®Google Scholar