Silica Sulfuric Acid (SSA)/Polyethylene Glycol (PEG) as a Recyclable System for the Synthesis of Quinoxalines and Pyrazines

REFERENCES

• (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 . Anti-Cancer Drug Des. 1999 , 15 , 291 .
   PubMed Web of Science ®Google Scholar
• (a) Li , W. ; Fuchs , P. L. An efficient synthesis of the c-23 deoxy, 17 α-hydroxy south 1 hemisphere and its cephalostatin 1 analog . Org. Lett. 2003 , 5 , 2849 ; (b) Buron , F. ; Plé , N. ; Turck , A. ; Gueguiner , G. Synthesis of pyrazine alkaloids from botryllus leachi: Diazines 43 . J. Org. Chem. 2005 , 70 , 2616 ; (c) Fukuwatari , T. ; Sugimoto , E. ; Shibata , K. Growth-promoting activity of pyrazinoic acid, a putative active compound of antituberculosis drug pyrazinamide, in niacin-deficient rats through the inhibition of ACMSD activity . Biosci. Biotech. Biochem. 2002 , 66 , 1435 ; (d) Cynamon , M. H. ; Speirs , R. J. ; Welch , J. T. In vitro antimycobacterial activity of 5-chloropyrazinamide . Antimicrob. Agents Chemother. 1998 , 42 , 462 .
   PubMed Web of Science ®Google Scholar
• (a) Bhosale , R. S. ; Sarda , S. R. ; Andhapure , 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 ; (b) Aparicio , D. ; Attanasi , O. A. ; Filippone , P. ; Ignacio , R. ; Lillini , S. ; Mantellini , F. ; Palacios , F. ; de los Santos , J. M. Straightforward access to pyrazines, piperazinones, and quinoxalines by reactions of 1,2-diaza-1,3-butadienes with 1,2-diamines under solution, solvent-free, or solid-phase conditions . J. Org. Chem. 2006 , 71 , 5897 ; (c) 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 ; (d) Antoniotti , S. ; Duñach , E. Direct and catalytic synthesis of quinoxaline derivatives from epoxides and ene-1,2-diamines . Tetrahedron Lett. 2002 , 43 , 3971 ; (e) Wu , Z. ; Ede , N. J. Solid-phase synthesis of quinoxalines on SynPhase™ lanterns . Tetrahedron Lett. 2001 , 42 , 8115 ; (f) Singh , S. K. ; Gupta , P. ; Duggineni , S. ; Kundu , B. Solid-phase synthesis of quinoxalines . Synlett 2003 , 14 , 2147 ; (g) Zhou , J. F. ; Gong , G. X. ; An , L. T. ; Liu , Y. An efficient synthesis of quinoxalines under catalyst-free and microwave-irradiation conditions . Synlett 2008 , 20 , 3163 ; (h) Vara , Y. ; Aldaba , E. ; Arrieta , A. ; Pizarro , J. L. ; Arriortua , M. I. Regiochemistry of the microwave-assisted reaction between aromatic amines and α-bromoketones to yield substituted 1H-indoles . Org. Biomol. Chem. 2008 , 6 , 1763 ; (i) Das , B. ; Venkateswarlu , K. ; Suneel , K. ; Majhi , A. An efficient and convenient protocol for the synthesis of quinoxalines and dihydropyrazines via cyclization–oxidation processes using HClO4 · SiO2 as a heterogeneous recyclable catalyst . Tetrahedron Lett. 2007 , 48 , 5371 ; (j) Neto , B. A. D. ; Lopes , A. S. ; Wust , M. ; Costa , V. E. U. Reductive sulfur extrusion reaction of 2,1,3-benzothiadiazole compounds: A new methodology using NaBH4/CoCl2 · 6H2O (cat) as the reducing system . Tetrahedron Lett. 2005 , 46 , 6843 ; (k) 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 ; (l) Darabi , H. R. ; Aghapoor , K. ; Mohsenzadeh , F. ; Taala , F. ; Asadollahnejad , N. ; Badiei , A. Silica-supported antimony(III) chloride as highly effective and reusable heterogeneous catalyst for the synthesis of quinoxalines . Catal. Lett. 2009 , 133 , 84 ; (m) Beheshtiha , Y. S. ; Heravi , M. M. ; Saeedi , M. ; Karimi , N. ; Zakeri , M. ; Tavakoli-Hossieni , N. Efficient and green synthesis of 1,2-disubstituted benzimidazoles and quinoxalines using Bronsted acid ionic liquid, [(CH2)4SO3HMIM][HSO4], in water at room temperature . Synth. Commun. 2010 , 40 , 1216 .
   Web of Science ®Google Scholar
• (a) Douglass , F. ; Taber , D. F. ; DeMatteo , P. W. ; Taluskie , K. V. Synthesis of symmetrical and unsymmetrical pyrazines . J. Org. Chem. 2007 , 72 , 1492 ; (b) Elmaaty , T. A. ; Castle , L. W. Facile regiocontrolled synthesis of trialkyl-substituted pyrazines . Org. Lett. 2005 , 7 , 5529 .
   PubMed Web of Science ®Google Scholar
• (a) Cho , C. S. ; Oh , S. G. Copper-catalyzed oxidative cyclization of α-hydroxyketones with o-phenylenediamines leading to quinoxalines. J. Mol. Catal. A: Chem. 2007, 276, 205; (b) Cho , C. S. ; Ren , W. X. A recyclable copper catalysis in quinoxaline synthesis from α-hydroxyketones and o-phenylenediamines. J. Organomet. Chem. 2009, 694, 3215.
   Web of Science ®Google Scholar
• Rao , K. T. V. ; Prasad , P. S. S. ; Lingaiah , N. Iron-exchanged molybdophosphoric acid as an efficient heterogeneous catalyst for the synthesis of quinoxalines . J. Mol. Cat. A: Chem. 2009 , 312 , 65 .
   Web of Science ®Google Scholar
• Jeena , V. ; Robinson , R. S. Green oxidations: Titanium dioxide–induced tandem oxidation coupling reactions . Beilstein J. Org. Chem. 2009 , 5 , 24 .
   PubMed Web of Science ®Google Scholar
• (a) 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 ; (b) 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 , 2 , 788 .
   Web of Science ®Google Scholar
• Shaabani , A. ; Maleki , A. Green and efficient synthesis of quinoxaline derivatives via ceric ammonium nitrate–promoted and in situ aerobic oxidation of α-hydroxy ketones and α-keto oximes in aqueous media . Chem. Pharm. Bull. 2008 , 56 , 79 .
   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 catalyzed aerobic oxidation . Synlett 2005 , 6 , 1003 .
   Google Scholar
• Kotharkar , S. A. ; Shinde , D. B. Mercuric iodide (HgI2) as an oxidizing agent for the synthesis of quinoxalines . Bull. Korean Chem. Soc. 2006 , 27 , 1466 .
   Web of Science ®Google Scholar
• Sithambaram , S. ; Ding , Y. ; Li , W. ; Shen , X. ; Gaenzlera , F. ; Suib , S. L. Manganese octahedral molecular sieves–catalyzed tandem process for synthesis of quinoxalines . Green Chem. 2008 , 10 , 1029 .
   Web of Science ®Google Scholar
• (a) Mohsenzadeh , F. ; Aghapoor , K. ; Darabi , H. R. Benign approaches for the microwave-assisted synthesis of quinoxalines . J. Braz. Chem. Soc. 2007 , 18 , 297 ; (b) Feng , J. C. ; Liu , Y. ; Meng , Q. H. ; Liu , B. The synthesis of quinoxalines by condensation reaction of acyloins with o-phenylenediamine without solvent under microwave irradiation . Synth. Commun. 1998 , 28 , 193 ; (c) Kim , S. Y. ; Park , K. H. ; Chung , Y. K. Manganese(IV) dioxide–catalyzed synthesis of quinoxalines under microwave irradiation . Chem. Commun. 2005 , 1321 .
   Web of Science ®Google Scholar
• (a) Salehi , P. ; Zolfigol , M. A. ; Shirini , F. ; Baghbanzadeh , M. Silica sulfuric acid and silica chloride as efficient reagents for organic reactions . Curr. Org. Chem. 2006 , 10 , 2171 ; (b) Salehi , P. ; Dabiri , M. ; Zolfigol , M. A. Silica sulfuric acid as an efficient and reusable reagent for crossed-aldol condensation of ketones with aromatic aldehydes under solvent-free conditions . J. Braz. Chem. Soc. 2004 , 15 , 773 ; (c) Salehi , P. ; Dabiri , M. ; Zolfigol , M. A. Silica sulfuric acid: An efficient and reusable catalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones . Tetrahedron Lett. 2003 , 44 , 2889 ; (d) Habibi , Z. ; Salehi , P. ; Zolfigol , M. A. A novel one-pot synthesis of unsymmetrical acyclic imides . Synlett 2007 , 812 ; (e) Zolfiol , M. A. Silica sulfuric acid/NaNO2 as a novel heterogeneous system for production of thionitrites and disulfides under mild conditions . Tetrahedron 2001 , 57 , 9509 ; (f) Salehi , P. ; Dabiri , M. ; Zolfigol , M. A. A new approach to the facile synthesis of mono- and disubstituted quinazolin-4(3H)-ones under solvent-free conditions . Tetrahedron Lett. 2005 , 46 , 7051 ; (g) Zolfigol , M. A. ; Shirini , F. ; Choghamarania , A. G. Silica modified sulfuric acid/NaNO2 as a novel heterogeneous system for the oxidation of 1,4-dihydropyridines under mild conditions . Green Chem. 2002 , 4 , 562 .
   Web of Science ®Google Scholar
• (a) Chen , J. X. ; Wu , H. Y. ; Jin , C. ; Zhang , X. X. ; Xie , Y. Y. ; Su , W. K. Highly regioselective ringopening of epoxides with thiophenols in ionic liquids without the use of any catalyst. Green Chem. 2006, 8, 330; (b) Chen , J. X. ; Wu , H. Y. ; Zheng , Z. G. ; Jin , C. ; Zhang , X. X. ; Su , W. K. An approach to the Paal–Knorr pyrroles synthesis catalyzed by Sc(OTf)3 under solvent-free conditions. Tetrahedron Lett. 2006, 47, 5383; (c) Chen , X. A. ; Zhang , C. F. ; Wu , H. Y. ; Yu , X. C. ; Su , W. K. ; Cheng , J. Solvent-free synthesis of β-hydroxy esters and β-amino esters by indium-mediated Reformatsky reaction. Synthesis 2007, 3233; (d) Chen , J. X. ; Su , W. K. ; Wu , H. Y. ; Liu , M. C. ; Jin , C. Eco-friendly synthesis of 2,3-dihydroquinazolin-4(1H)-ones in ionic liquids or ionic liquid–water without additional catalyst. Green Chem. 2007, 9, 972; (e) Chen , J. X. ; Wu , D. Z. ; He , F. ; Liu , M. C. ; Wu , H. Y. ; Ding , J. C. ; Su , W. K. Gallium(III) triflate–catalyzed one-pot selective synthesis of 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones. Tetrahedron Lett. 2008, 49, 3814; (f) Zhang , C. F. ; Chen , J. X. ; Yu , X. C. ; Chen , X. A. ; Wu , H. Y. ; Yu , J. P. B2O3/Al2O3 as an efficient and recyclable catalyst for the synthesis of β-amino alcohols under solvent-free conditions. Synth. Commun. 2008, 38, 1875; (g) Zhu , D. J. ; Chen , J. X. ; Xiao , H. L. ; Liu , M. C. ; Ding , J. C. ; Wu , H. Y. Efficient and expeditious synthesis of di- and trisubstituted thiazoles in PEG under catalyst-free conditions. Synth. Commun. 2009, 39, 2895; (i) Chen , J. X. ; Yang , X. L. ; Liu , M. C. ; Wu , H. Y. ; Ding , J. C. ; Su , W. K. Approach to synthesis of β-enamino ketones and pyrroles catalyzed by gallium(III) triflate under solvent-free conditions. Synth. Commun. 2009, 39, 4180; (j) Guo , W. X. ; Lv , G. S. ; Chen , J. X. ; Gao , W. X. ; Ding , J. C. ; Wu , H. Y. Rongalite® and base-promoted cleavage of disulfides and subsequent Michael addition to α,β-unsaturated ketones/esters: An odorless synthesis of β-sulfido carbonyl compounds. Tetrahedron 2010, 66, 2297; (k) Cai , M. T. ; Lv , G. S. ; Chen , J. X. ; Gao , W. X. ; Ding , J. C. ; Wu , H. Y. CAN/I2-catalyzed chemoselective synthesis of thiosulfonates by oxidation of disulfides or thiols. Chem. Lett. 2010, 39, 368.
   Web of Science ®Google Scholar
• Hasaninejad , A. ; Zare , A. ; Mohammadizadeh , M. R. ; Shekouhya , M. Oxalic acid as an efficient, cheap, and reusable catalyst for the preparation of quinoxalines via condensation of 1,2-diamines with α-diketones at room temperature . Arkivoc 2008 , 13 , 28 .
   Web of Science ®Google Scholar
• Cai , J. J. ; Zou , J. P. ; Pan , X. Q. ; Zhang , W. Gallium(III) triflate–catalyzed synthesis of quinoxaline derivatives . Tetrahedron Lett. 2008 , 49 , 7386 .
   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, efficient, and green approach to the synthesis of quinoxalines . Green Chem. 2006 , 8 , 91 .
   Web of Science ®Google Scholar
• Yadav , J. S. ; Subba Reddy , B. V. ; Premalatha , K. ; Shankar , K. S. Bismuth(III)-catalyzed rapid synthesis of 2,3-disubstituted quinoxalines in water . Synthesis 2008 , 3787 .
   Web of Science ®Google Scholar
• Akita , Y. ; Ohta , A. Unusual Friedel–Crafts reactions, 3(1): Synthesis of 2,4-diethoxychromans and their conversion into benzopyrylium perchlorates . Heterocycles 1981 , 16 , 1325 .
   Google Scholar
• Ohta , A. ; Inoue , A. ; Watanabe , T. Introduction of the methyl group into the pyrazine ring . Heterocycles 1984 , 22 , 2317 .
   Web of Science ®Google Scholar
• Ellis , M. J. ; Lloyd , D. ; McNab , H. ; Walkera , M. J. Gas-phase pyrolysis of 2,3-dihydro-1,4-diazepines: Involvement of the saturated portion of the ring in chemical reactions and novel cis-trans isomerization of a fused ring system . J. Chem. Soc., Chem. Commun. 1995 , 2337 .
   Google Scholar
• Saikachi , H. ; Matsuo , J. Synthesis of furan derivatives, XXXIV: Preparation of 2,3-bis(5-nitro-2-furyl)pyrazine derivatives . Yakugaku Zasshi 1966 , 86 , 927 .
   PubMedGoogle Scholar
• Khuhawar , M. Y. ; Memon , Z. P. Qualitative studies of reactions of furyl-substituted pyrazine and quinoxaline ligands towards some metal ions . Pak. J. Sci. Ind. Res. 1987 , 30 , 338 .
   Google Scholar
• Jimeno , M. L. ; de Paz , J. L. G. ; Rodriguez , J. ; Rodriguez , M. ; Ochoa , C. 2,3-Disubstituted hexahydro- and tetrahydroquinoxalines: Synthesis and a theoretical and experimental dynamic NMR study . An. Quim. 1994 , 90 , 423 .
   Google Scholar