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Volumn 40, Issue 14, 2010, Pages 2047-2056

Efficient, ecofriendly, and practical process for the synthesis of quinoxalines catalyzed by amberlyst-15 in aqueous media

Author keywords

1,2 diamine; 1,2 diketone; Amberlyst 15; Quinoxaline; Water

Indexed keywords

AMBERLYST 15; QUINOXALINE DERIVATIVE; RESIN; UNCLASSIFIED DRUG; WATER;

EID: 77953711092     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903219401     Document Type: Article
Times cited : (42)

References (44)
  • 1
    • 0036703508 scopus 로고    scopus 로고
    • Stereoselective organic reactions in water
    • Lindstroem, U. M. Stereoselective organic reactions in water. Chem. Rev. 2002, 102, 2751.
    • (2002) Chem. Rev. , vol.102 , pp. 2751
    • Lindstroem, U.M.1
  • 2
    • 33751431007 scopus 로고    scopus 로고
    • Significant rate acceleration of the aza-Michael reaction in water
    • Ranu, B. C.; Banerjee, S. Significant rate acceleration of the aza-Michael reaction in water. Tetrahedron Lett. 2007, 48, 141.
    • (2007) Tetrahedron Lett. , vol.48 , pp. 141
    • Ranu, B.C.1    Banerjee, S.2
  • 3
    • 0002181129 scopus 로고
    • S. Patai (Ed.); Interscience: New York
    • (a)Gibson, M. S. In The Chemistry of Amino Group; S. Patai (Ed.); Interscience: New York, 1968; p. 61;
    • (1968) The Chemistry of Amino Group , pp. 61
    • Gibson, M.S.1
  • 5
    • 12444339774 scopus 로고    scopus 로고
    • Potent quinoxaline-based inhibitors of PDGF receptor tyrosine kinase activity, part 2: The synthesis and biological activities of RPR127963, an orally bioavailable inhibitor
    • (a)He, W.; Meyers, M. R.; Hanney, B.; Spada, A.; Blider, G.; Galzeinski, H.; Amin, D.; Needle, S.; Page, K.; Jayyosi, Z.; Perrone, H. Potent quinoxaline-based inhibitors of PDGF receptor tyrosine kinase activity, part 2: The synthesis and biological activities of RPR127963, an orally bioavailable inhibitor. Bioorg. Med. Chem. Lett. 2003, 13, 3097;
    • (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 3097
    • He, W.1    Meyers, M.R.2    Hanney, B.3    Spada, A.4    Blider, G.5    Galzeinski, H.6    Amin, D.7    Needle, S.8    Page, K.9    Jayyosi, Z.10    Perrone, H.11
  • 6
    • 0346729859 scopus 로고    scopus 로고
    • Synthesis and biological activity of new quinoxaline antibiotics of echinomycin analogues
    • (b)Kim, Y. B.; Kim, Y. H.; Park, J. Y.; Kim, S. K. Synthesis and biological activity of new quinoxaline antibiotics of echinomycin analogues. Bioorg. Med. Chem. Lett. 2004, 14, 541.
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 541
    • Kim, Y.B.1    Kim, Y.H.2    Park, J.Y.3    Kim, S.K.4
  • 8
    • 18144408330 scopus 로고    scopus 로고
    • Chromophore-labeled quinoxaline derivatives as efficient electroluminescent materials
    • 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.
    • (2005) Chem. Mater. , vol.17 , pp. 1860
    • Thomas, K.R.J.1    Velusamy, M.2    Lin, J.T.3    Chuen, C.H.4    Tao, Y.T.5
  • 9
    • 0034842923 scopus 로고    scopus 로고
    • Synthesis and device characterisation of side-chain polymer electron transport materials for organic semiconductor applications
    • Dailey, S.; Feast, J. W.; Peace, R. J.; Saga, R. 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.
    • (2001) J. Mater. Chem. , vol.11 , pp. 2238
    • Dailey, S.1    Feast, J.W.2    Peace, R.J.3    Saga, R.C.4    Till, S.5    Wood, E.L.6
  • 11
    • 0037034055 scopus 로고    scopus 로고
    • Molecular design and evaluation of quinoxaline-carbohydrate hybrids as novel and efficient photo-induced GG-selective DNA cleaving agents
    • (b)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;
    • (2002) Chem. Commun. , vol.212
    • Kazunobu, T.1    Ryusuke, T.2    Tomohiro, O.3    Shuichi, M.4
  • 12
    • 0038441601 scopus 로고    scopus 로고
    • 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
    • (c)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.
    • (2003) J. Org. Chem. , vol.68 , pp. 4179
    • Hegedus, L.S.1    Marc, M.G.2    Jory, J.W.3    Joseph, P.B.4
  • 13
    • 84934875775 scopus 로고    scopus 로고
    • E. C. Taylor and P. Wipf (Eds.); John Wiley and Sons: Upper Saddle River, NJ
    • Brown, D. J. In The Chemistry of Heterocyclic Compounds; E. C. Taylor and P. Wipf (Eds.); John Wiley and Sons: Upper Saddle River, NJ, 2004.
    • (2004) The Chemistry of Heterocyclic Compounds
    • Brown, D.J.1
  • 14
    • 0037182322 scopus 로고    scopus 로고
    • Direct and catalytic synthesis of quinoxaline derivatives from epoxides and ene-1,2-diamines
    • Antoniotti, S.; Donach, E. Direct and catalytic synthesis of quinoxaline derivatives from epoxides and ene-1,2-diamines. Tetrahedron Lett. 2002, 43, 3971.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 3971
    • Antoniotti, S.1    Donach, E.2
  • 15
  • 17
    • 0037064524 scopus 로고    scopus 로고
    • The first microwave-assisted regiospecific synthesis of 6-substituted pterins
    • (a)Shymaprosad, G.; Avijit, K. A. The first microwave-assisted regiospecific synthesis of 6-substituted pterins. Tetrahedron Lett. 2002, 43, 8371;
    • (2002) Tetrahedron Lett. , vol.43 , pp. 8371
    • Shymaprosad, G.1    Avijit, K.A.2
  • 18
    • 2942519827 scopus 로고    scopus 로고
    • General microwave-assisted protocols for the expedient synthesis of quinoxalines and heterocyclic pyrazines
    • (b)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.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 4873
    • Zhao, Z.1    Wisnoski, D.D.2    Wolkenberg, S.E.3    Leister, W.H.4    Wang, Y.5    Lindsley, C.W.6
  • 19
    • 17144375635 scopus 로고    scopus 로고
    • Quinoxaline synthesis from a-hydroxy ketones via a tandem oxidation process using catalysed aerobic oxidation
    • Robinson, R. S.; Taylor, R. J. K. Quinoxaline synthesis from a-hydroxy ketones via a tandem oxidation process using catalysed aerobic oxidation. Synlett 2005, 6, 1003.
    • (2005) Synlett , vol.6 , pp. 1003
    • Robinson, R.S.1    Taylor, R.J.K.2
  • 20
    • 1642413403 scopus 로고    scopus 로고
    • Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds
    • 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.
    • (2004) Org. Biomol. Chem. , vol.2 , pp. 788
    • Raw, S.A.1    Wilfred, C.D.2    Taylor, R.J.K.3
  • 21
    • 20444494902 scopus 로고    scopus 로고
    • Heteroannulation of nitroketene N,S-arylaminoacetals with POCl3: A novel highly regioselective synthesis of unsymmetrical 2,3-substituted quinoxalines
    • Venkatesh, C; Singh, B.; Mahata, P. K.; Ha, 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.
    • (2005) Org. Lett. , vol.7 , pp. 2169
    • Venkatesh, C.1    Singh, B.2    Mahata, P.K.3    Ha, H.4    Junjappa, H.5
  • 22
    • 24944446763 scopus 로고    scopus 로고
    • An efficient protocol for the synthesis of quinoxaline derivatives at room temperature using molecular iodine as the catalyst
    • 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.
    • (2005) Tetrahedron Lett. , vol.46 , pp. 7183
    • Bhosale, R.S.1    Sarda, S.R.2    Ardhapure, S.S.3    Jadhav, W.N.4    Bhusare, S.R.5    Pawar, R.P.6
  • 23
    • 0141567587 scopus 로고    scopus 로고
    • Preparation of quinoxalines, dihydropyr-azines, pyrazines, and piperazines using tandem oxidation processes
    • Steven, A. R.; Cecilia, D. W.; Richard, J. K. T. Preparation of quinoxalines, dihydropyr-azines, pyrazines, and piperazines using tandem oxidation processes. Chem. Commun. 2003, 2286.
    • (2003) Chem. Commun. , vol.2286
    • Steven, A.R.1    Cecilia, D.W.2    Richard, J.K.T.3
  • 24
    • 33845537940 scopus 로고    scopus 로고
    • A recyclable and highly effective sulfamic acid/MeOH catalytic system for the synthesis of quinoxalines at room temperature
    • Darabi, H. R.; Mohandessi, S.; Aghapoor, K.; Mohsenzadeh, F. A recyclable and highly effective sulfamic acid/MeOH catalytic system for the synthesis of quinoxalines at room temperature. Catal. Commun. 2007, 8, 389.
    • (2007) Catal. Commun. , vol.8 , pp. 389
    • Darabi, H.R.1    Mohandessi, S.2    Aghapoor, K.3    Mohsenzadeh, F.4
  • 25
    • 39349108390 scopus 로고    scopus 로고
    • Montmorillonite K-10: An efficient and reusable catalyst for the synthesis of quinoxaline derivatives in water
    • 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.
    • (2008) Catal. Commun. , vol.9 , pp. 1143
    • Huang, T.K.1    Wang, R.2    Shi, L.3    Lu, X.X.4
  • 26
    • 33847687134 scopus 로고    scopus 로고
    • Efficient convenient, and reusable polyaniline-sulfate salt catalyst for the synthesis of quinoxaline derivatives
    • 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.
    • (2007) J. Mol. Catal. A: Chem. , vol.265 , pp. 227
    • Srinivas, C.1    Kumar, C.N.S.S.P.2    Jayathirtha Rao, V.3    Palaniappan, S.4
  • 27
    • 51849100390 scopus 로고    scopus 로고
    • Efficient synthesis of quinoxaline derivatives catalyzed by p-toluenesulfonic acid under solvent-free conditions
    • Shi, D. Q.; Dou, G. L. Efficient synthesis of quinoxaline derivatives catalyzed by p-toluenesulfonic acid under solvent-free conditions. Synth. Commun. 2008, 38, 3329.
    • (2008) Synth. Commun. , vol.38 , pp. 3329
    • Shi, D.Q.1    Dou, G.L.2
  • 28
    • 34248150492 scopus 로고    scopus 로고
    • Wells-Dawson-type heteropolyacid catalyzed synthesis of quinoxaline derivatives at room temperature
    • Heravi, M. M.; Bakhtiari, K.; Bamoharram, F. F.; Tehrani, M. H. Wells-Dawson-type heteropolyacid catalyzed synthesis of quinoxaline derivatives at room temperature. Monatsh. Chem. 2007, 138, 465.
    • (2007) Monatsh. Chem. , vol.138 , pp. 465
    • Heravi, M.M.1    Bakhtiari, K.2    Bamoharram, F.F.3    Tehrani, M.H.4
  • 29
    • 35148839611 scopus 로고    scopus 로고
    • Efficient and green method for the synthesis of 1,5-benzodiazepine and quinoxaline derivatives in water
    • 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.
    • (2007) Synth. Commun. , vol.37 , pp. 3447
    • Hazarika, P.1    Gogoi, P.2    Konwar, D.3
  • 30
    • 40749091661 scopus 로고    scopus 로고
    • MnCl2-promoted synthesis of quinoxaline derivatives at room temperature
    • Heravi, M. M.; Bakhtiari, K.; Oskooie, H. A.; Taheri, S. MnCl2-promoted synthesis of quinoxaline derivatives at room temperature. Heteroat. Chem. 2008, 19, 218.
    • (2008) Heteroat. Chem. , vol.19 , pp. 218
    • Heravi, M.M.1    Bakhtiari, K.2    Oskooie, H.A.3    Taheri, S.4
  • 32
    • 34447503639 scopus 로고    scopus 로고
    • Zn[(l)proline]: A powerful catalyst for the very fast synthesis of quinoxaline derivatives at room temperature
    • 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.
    • (2007) Catal. Commun. , vol.8 , pp. 1341
    • Heravi, M.M.1    Tehrani, M.H.2    Bakhtiari, K.3    Oskooie, H.A.4
  • 33
    • 33645404779 scopus 로고    scopus 로고
    • Cerium(IV) ammonium nitrate (CAN) as a catalyst in tap water: A simple, proficient, and green approach for the synthesis of quinoxalines
    • 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.
    • (2006) Green Chem. , vol.8 , pp. 91
    • More, S.V.1    Sastry, M.N.V.2    Yao, C.F.3
  • 34
    • 55549140786 scopus 로고    scopus 로고
    • Gallium(III) triflate-catalyzed synthesis of quinoxaline derivatives
    • Cai, J. J.; Zou, J. P.; Pan, X. Q.; Zhang, W. Gallium(III) triflate-catalyzed synthesis of quinoxaline derivatives. Tetrahedron Lett. 2008, 49, 7386.
    • (2008) Tetrahedron Lett. , vol.49 , pp. 7386
    • Cai, J.J.1    Zou, J.P.2    Pan, X.Q.3    Zhang, W.4
  • 35
    • 42749086835 scopus 로고    scopus 로고
    • Direct preparation of dichloropropanol (DCP) from glycerol using heteropolyacid (HPA) catalysts: A catalyst screen study
    • Lee, S. H.; Park, D. R.; Kim, H.; Lee, J.; Jung, J. C; Woo, S. Y.; Song, W. S.; Kwon, M. S.; Song, I. K. Direct preparation of dichloropropanol (DCP) from glycerol using heteropolyacid (HPA) catalysts: A catalyst screen study. Catal. Commun. 2008, 9, 1920.
    • (2008) Catal. Commun. , vol.9 , pp. 1920
    • Lee, S.H.1    Park, D.R.2    Kim, H.3    Lee, J.4    Jung, J.C.5    Woo, S.Y.6    Song, W.S.7    Kwon, M.S.8    Song, I.K.9
  • 36
    • 43049168326 scopus 로고    scopus 로고
    • K Epoxidation of propylene with hydrogen peroxide over TS-1 catalyst synthesized in the presence of polystyrene
    • Park, S.; Cho, K. M.; Youn, M. H.; Seo, J. G.; Baeck, S.-H.; Kim, T. J.; Chung, Y.-M.; Oh, S.-H.; Song, I. K Epoxidation of propylene with hydrogen peroxide over TS-1 catalyst synthesized in the presence of polystyrene. Catal. Lett. 2008, 122, 349.
    • (2008) Catal. Lett. , vol.122 , pp. 349
    • Park, S.1    Cho, K.M.2    Youn, M.H.3    Seo, J.G.4    Baeck, S.-H.5    Kim, T.J.6    Chung, Y.-M.7    Oh, S.-H.8    Song, I.9
  • 37
    • 0344897681 scopus 로고    scopus 로고
    • Heteropolyacid (HPA)-polymer composite films as heterogeneous catalysts and catalytic membranes
    • Song, I. K.; Lee, W. Y. Heteropolyacid (HPA)-polymer composite films as heterogeneous catalysts and catalytic membranes. Appl. Catal. A: Gen. 2003, 256, 77.
    • (2003) Appl. Catal. A: Gen. , vol.256 , pp. 77
    • Song, I.K.1    Lee, W.Y.2
  • 38
    • 33645410989 scopus 로고    scopus 로고
    • An efficient direct conversion of THP ethers into acetates using amberlyst-15
    • (a)Das, B.; Reddy, M. R.; Ramu, R.; Thirupathi, P. An efficient direct conversion of THP ethers into acetates using amberlyst-15. J. Mol. Catal. A: Chem. 2006,248,185;
    • (2006) J. Mol. Catal. A: Chem. , vol.248 , pp. 185
    • Das, B.1    Reddy, M.R.2    Ramu, R.3    Thirupathi, P.4
  • 39
    • 33947730988 scopus 로고    scopus 로고
    • Amberlyst-15: A mild, efficient, and reusable heterogeneous catalyst for Michael addition of pyrroles to a,b-unsaturated ketones
    • (b)Das, B.; Damodar, K.; Chowdhury, N. Amberlyst-15: A mild, efficient, and reusable heterogeneous catalyst for Michael addition of pyrroles to a,b-unsaturated ketones. J. Mol. Catal. A: Chem. 2007, 269, 81;
    • (2007) J. Mol. Catal. A: Chem. , vol.269 , pp. 81
    • Das, B.1    Damodar, K.2    Chowdhury, N.3
  • 40
    • 33846590105 scopus 로고    scopus 로고
    • Amberlyst-15: An efficient reusable heterogeneous catalyst for aza-Michael reactions under solvent-free conditions
    • (c)Das, B.; Chowdhury, N. Amberlyst-15: An efficient reusable heterogeneous catalyst for aza-Michael reactions under solvent-free conditions. J. Mol. Catal. A: Chem. 2007, 263, 212;
    • (2007) J. Mol. Catal. A: Chem. , vol.263 , pp. 212
    • Das, B.1    Chowdhury, N.2
  • 41
    • 34948903704 scopus 로고    scopus 로고
    • Amberlyst-15 as a heterogeneous reusable catalyst for the synthesis of a-hydroxy phosphonates in water
    • (d)Tajbakhsh, M.; Heydari, A.; Khalilzadeh, M. A.; Lakouraj, M. M.; Zamenian, B.; Khaksar, S. Amberlyst-15 as a heterogeneous reusable catalyst for the synthesis of a-hydroxy phosphonates in water. Synlett 2007, 2347;
    • (2007) Synlett , vol.2347
    • Tajbakhsh, M.1    Heydari, A.2    Khalilzadeh, M.A.3    Lakouraj, M.M.4    Zamenian, B.5    Khaksar, S.6
  • 42
    • 55549108022 scopus 로고    scopus 로고
    • Amberlyst-15 as a new and reusable catalyst for regioselective ring-opening reactions of epoxides to b-alkoxy alcohols
    • (e)Liu, Y.-H.; Liu, Q.-S, Zhang, Z.-H. Amberlyst-15 as a new and reusable catalyst for regioselective ring-opening reactions of epoxides to b-alkoxy alcohols. J. Mol. Catal. A: Chem. 2008, 296, 42;
    • (2008) J. Mol. Catal. A: Chem. , vol.296 , pp. 42
    • Liu, Y.-H.1    Liu, Q.-S.2    Zhang, Z.-H.3
  • 44
    • 84944048121 scopus 로고
    • A. R. Katritzkyand C. Rees (Eds.); Pergamon: Oxford
    • (f)Porter, A. E. A. In Comprehensive Heterocyclic Chemistry; A. R. Katritzkyand, C. Rees (Eds.); Pergamon: Oxford, 1984; pp. 157-197.
    • (1984) Comprehensive Heterocyclic Chemistry , pp. 157-197
    • Porter, A.E.A.1


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