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Volumn 38, Issue 19, 2008, Pages 3329-3337

Efficient synthesis of quinoxaline derivatives catalyzed by p-toluenesulfonic acid under solvent-free conditions

Author keywords

p Toluenesulfonic acid; Quinoxaline; Room temperature; Solvent free conditions

Indexed keywords

DIAMINE; DIKETONE; QUINOXALINE DERIVATIVE; SOLVENT; TOLUENESULFONIC ACID DERIVATIVE;

EID: 51849100390     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802136664     Document Type: Article
Times cited : (37)

References (34)
  • 1
    • 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, 3097-3099;
    • (2003) Bioorg. Med. Chem. Lett , vol.13 , pp. 3097-3099
    • 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
  • 2
    • 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. K.; Kim, S. K. Synthesis and biological activity of new quinoxaline antibiotics of echinomycin analogues. Bioorg. Med. Chem. Lett. 2004, 14, 541-544.
    • (2004) Bioorg. Med. Chem. Lett , vol.14 , pp. 541-544
    • Kim, Y.B.1    Kim, Y.H.2    Park, J.K.3    Kim, S.K.4
  • 3
    • 0034842923 scopus 로고    scopus 로고
    • Synthesis and device characterization 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 characterization of side-chain polymer electron transport materials for organic semiconductor applications. J. Mater. Chem. 2001, 11, 2238-2243.
    • (2001) J. Mater. Chem , vol.11 , pp. 2238-2243
    • Dailey, S.1    Feast, J.W.2    Peace, R.J.3    Saga, R.C.4    Till, S.5    Wood, E.L.6
  • 4
    • 18144408330 scopus 로고    scopus 로고
    • Chromophore-labeled quinoxaline derivatives as efficient electroluminescent materials
    • 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.
    • (2005) Chem. Mater , vol.17 , pp. 1860
    • Justin Thomas, K.R.1    Marappan, V.2    Jiann, T.L.3    Chang-Hao, C.4    Yu-ai, T.5
  • 5
    • 0030213929 scopus 로고    scopus 로고
    • Use of poly(phenylquinoxaline) as an electron transport material in polymer light-emitting diodes
    • O'Brien, D.; Weaver, M. S.; Lidzey, D. G.; Bradley, D. D. C. Use of poly(phenylquinoxaline) as an electron transport material in polymer light-emitting diodes. Appl. Phys. Lett. 1996, 69, 881-883.
    • (1996) Appl. Phys. Lett , vol.69 , pp. 881-883
    • O'Brien, D.1    Weaver, M.S.2    Lidzey, D.G.3    Bradley, D.D.C.4
  • 8
    • 1342306675 scopus 로고    scopus 로고
    • Quinoxaline excision: A novel approach to tri- and diquinoxaline cavitands
    • (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, 333-336.
    • (2004) Org. Lett , vol.6 , pp. 333-336
    • Peter, P.C.1    Gang, Z.2    Grace, A.M.3    Carlos, H.4    Linda, M.G.T.5
  • 9
    • 3943058154 scopus 로고    scopus 로고
    • Sascha, O.; Rudiger, F. Quinoxalinodehydroannulenes: A novel class of carbon-rich materials. Synlett. 2004, 1509-1512.
    • Sascha, O.; Rudiger, F. Quinoxalinodehydroannulenes: A novel class of carbon-rich materials. Synlett. 2004, 1509-1512.
  • 10
    • 0037034055 scopus 로고    scopus 로고
    • Molecular design and evaluation of quinoxaline-carbohydrate hybrids as novel and efficient photo-induced GG-selective DNA cleaving agents
    • (a) Kazunobu; 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, 212-213;
    • (2002) Chem. Commun , pp. 212-213
    • Kazunobu1    Ryusuke, T.2    Tomohiro, O.3    Shuichi, M.4
  • 11
    • 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
    • (b) Louis, 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
    • Louis, S.1    Marc, M.G.2    Jory, J.W.3    Joseph, P.B.4
  • 12
    • 51849094345 scopus 로고    scopus 로고
    • Supplement II
    • E. C. Taylor, P. Wipf Eds, John Wiley & Sons: Newark, NJ
    • Brown, D. J. Quinoxalines: Supplement II; In The Chemistry of Heterocyclic Compounds; E. C. Taylor, P. Wipf (Eds.); John Wiley & Sons: Newark, NJ, 2004.
    • (2004) The Chemistry of Heterocyclic Compounds
    • Brown, D.J.Q.1
  • 13
    • 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, 3971-3974.
    • (2002) Tetrahedron Lett , vol.43 , pp. 3971-3974
    • Antoniotti, S.1    Donach, E.2
  • 14
    • 17144375635 scopus 로고    scopus 로고
    • Quinoxaline synthesis from α-hydroxy ketones via a tandem oxidation process using catalyzed aerobic oxidation
    • Robinson, R. S.; Taylor, R. J. K. Quinoxaline synthesis from α-hydroxy ketones via a tandem oxidation process using catalyzed aerobic oxidation. Synlett. 2005, 1003-1005.
    • (2005) Synlett , pp. 1003-1005
    • Robinson, R.S.1    Taylor, R.J.K.2
  • 15
    • 0141567587 scopus 로고    scopus 로고
    • Preparation of quinoxalines, dihydropyrazines, pyrazines, and piperazines using tandem oxidation processes
    • (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, 2286-2287;
    • (2003) Chem. Commun , pp. 2286-2287
    • Raw, S.A.1    Wilfred, C.D.2    Taylor, R.J.K.3
  • 16
    • 1642413403 scopus 로고    scopus 로고
    • Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds
    • (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, 788-796.
    • (2004) Org. Biomol. Chem , vol.2 , pp. 788-796
    • Raw, S.A.1    Wilfred, C.D.2    Taylor, R.J.K.3
  • 17
    • 0034707362 scopus 로고    scopus 로고
    • Synthesis of quinoxalines by cyclization of α-arylimino oximes of α-dicarbonyl compounds
    • 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, 10299-10302.
    • (2000) Tetrahedron Lett , vol.41 , pp. 10299-10302
    • Xekoukoulotakis, N.P.1    Hadjiantonious, M.C.P.2    Maroulis, A.J.3
  • 18
    • 2942519827 scopus 로고    scopus 로고
    • General microwave-assisted protocols for the expedient synthesis of quinoxalines and heterocyclic pyrazines
    • 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, 4873-4876.
    • (2004) Tetrahedron Lett , vol.45 , pp. 4873-4876
    • Zhao, Z.1    Wisnoski, D.D.2    Wolkenberg, S.E.3    Leister, W.H.4    Wang, Y.5    Lindsley, C.W.6
  • 19
    • 23744463590 scopus 로고    scopus 로고
    • Molecular iodine: A powerful catalyst for the easy and efficient synthesis of quinoxalines
    • (a) 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;
    • (2005) Tetrahedron Lett , vol.46 , pp. 6345-6348
    • More, S.V.1    Sastry, M.N.V.2    Wang, C.C.3    Yao, C.F.4
  • 20
    • 24944446763 scopus 로고    scopus 로고
    • An efficient protocol for the synthesis of quinoxaline derivatives at room temperature using molecular iodine as the catalyst
    • (b) Bhosale, R. S.; Sarda, S. R.; Ardhapure, S. S.; Jadhav, W. N.; Rhusare, 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.
    • (2005) Tetrahedron Lett , vol.46 , pp. 7183-7186
    • Bhosale, R.S.1    Sarda, S.R.2    Ardhapure, S.S.3    Jadhav, W.N.4    Rhusare, S.R.5    Pawar, R.P.6
  • 21
    • 0035813415 scopus 로고    scopus 로고
    • Solid-phase synthesis of quinoxalines on synphase™ lanterns
    • (a) Wu, Z.; Ede, N. J. Solid-phase synthesis of quinoxalines on synphase™ lanterns. Tetrahedron Lett. 2001, 42, 8115-8118;
    • (2001) Tetrahedron Lett , vol.42 , pp. 8115-8118
    • Wu, Z.1    Ede, N.J.2
  • 23
    • 0038496922 scopus 로고    scopus 로고
    • Improved synthesis of substituted quinoxalines from new N = N-polymer-bound 1,2-diaza-1,3-butadienes
    • (c) Attanasi, O. A.; Crescentini, L. D.; Filippone, P.; Mantellini, F.; Santeusanio, S. Improved synthesis of substituted quinoxalines from new N = N-polymer-bound 1,2-diaza-1,3-butadienes. Synlett. 2003, 1183-1185.
    • (2003) Synlett , pp. 1183-1185
    • Attanasi, O.A.1    Crescentini, L.D.2    Filippone, P.3    Mantellini, F.4    Santeusanio, S.5
  • 24
    • 35948942317 scopus 로고    scopus 로고
    • Solvent-free carbon-carbon bond formations in ball mills
    • Belen, R.; Angelika, B.; Toni, R.; Carsten, B. Solvent-free carbon-carbon bond formations in ball mills. Adv. Synth. Catal. 2007, 349, 2213-2233.
    • (2007) Adv. Synth. Catal , vol.349 , pp. 2213-2233
    • Belen, R.1    Angelika, B.2    Toni, R.3    Carsten, B.4
  • 25
    • 0000884192 scopus 로고    scopus 로고
    • Solvent-free organic synthesis
    • Tanaka, K.; Toda, F. Solvent-free organic synthesis. Chem. Rev. 2000, 100, 1025-1074.
    • (2000) Chem. Rev , vol.100 , pp. 1025-1074
    • Tanaka, K.1    Toda, F.2
  • 29
    • 0037424799 scopus 로고    scopus 로고
    • Shi, D. Q.; Rong, L. C.; Wang, J. X.; Zhuang, Q. Y.; Wang, X. S.; Hu, H. W. Synthesis of quinazolin-4(3H)-ones and 1,2-dihydroquinazolin- 4(3H)-ones with the aid of a low-valent titanium reagent. Tetrahedron Lett. 2003, 44, 3199-3201;
    • (a) Shi, D. Q.; Rong, L. C.; Wang, J. X.; Zhuang, Q. Y.; Wang, X. S.; Hu, H. W. Synthesis of quinazolin-4(3H)-ones and 1,2-dihydroquinazolin- 4(3H)-ones with the aid of a low-valent titanium reagent. Tetrahedron Lett. 2003, 44, 3199-3201;
  • 30
    • 5644223408 scopus 로고    scopus 로고
    • An efficient synthesis of substituted pyrroles with the aid of low-valent titanium reagent
    • (b) Shi, D. Q.; Shi, C. L.; Wang, X. S.; Zhuang, Q. Y.; Tu, S. J.; Hu, H. W. An efficient synthesis of substituted pyrroles with the aid of low-valent titanium reagent. Synlett. 2004, 2239-2241.
    • (2004) Synlett , pp. 2239-2241
    • Shi, D.Q.1    Shi, C.L.2    Wang, X.S.3    Zhuang, Q.Y.4    Tu, S.J.5    Hu, H.W.6
  • 31
    • 33845522192 scopus 로고
    • The preparation of some substituted quinoxalines
    • Bost, R. W.; Towell, R. R. The preparation of some substituted quinoxalines. J. Am. Chem. Soc. 1948, 70, 903-905.
    • (1948) J. Am. Chem. Soc , vol.70 , pp. 903-905
    • Bost, R.W.1    Towell, R.R.2
  • 32
    • 0000191044 scopus 로고
    • Novel polycyclic dianions: Metal reduction of nitrogen heterocycles
    • Minsky, A.; Cohen, Y.; Rabinovitz, M. Novel polycyclic dianions: Metal reduction of nitrogen heterocycles. J. Am. Chem. Soc. 1985, 107, 1501-1505.
    • (1985) J. Am. Chem. Soc , vol.107 , pp. 1501-1505
    • Minsky, A.1    Cohen, Y.2    Rabinovitz, M.3
  • 34
    • 84981944952 scopus 로고
    • Photoinduced polymerization of methyl methacrylate in the presence of low- and high-molecular-weight quinoxaline derivatives
    • Braun, Q. Photoinduced polymerization of methyl methacrylate in the presence of low- and high-molecular-weight quinoxaline derivatives. Angew. Makromol. Chem. 1975, 43, 125-143.
    • (1975) Angew. Makromol. Chem , vol.43 , pp. 125-143
    • Braun, Q.1


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