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Volumn 44, Issue 10, 2014, Pages 1453-1460

O-iodoxy benzoic acid–mediated synthesis of 3,5-diarylisoxazoles and isoxazole-3-carboxylic acids

Author keywords

Chalcone; Isoxazoles; O iodoxybenzoic acid; Oxidative cyclization; unsaturated ketoxime

Indexed keywords

BENZOIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CHLOROFORM; ISOXAZOLE DERIVATIVE;

EID: 84987941277     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2013.854916     Document Type: Article
Times cited : (19)

References (40)
  • 1
    • 0037147937 scopus 로고    scopus 로고
    • Synthesis and oxidation of user- and ecofriendly hypervalent iodine reagent
    • Thottumkar, A. P.; Thottumkar, K. V. Synthesis and oxidation of user- and ecofriendly hypervalent iodine reagent. Tetrahedron Lett. 2002, 43, 569–572.
    • (2002) Tetrahedron Lett , vol.43 , pp. 569-572
    • Thottumkar, A.P.1    Thottumkar, K.V.2
  • 2
    • 4444255981 scopus 로고    scopus 로고
    • Hypervalent iodinemediated interaction of aldoximes with activated alkenes including Baylis–Hillman adducts: A new and efficient method for the preparation of nitrile oxides from aldoximes
    • Das, B.; Holla, H.; Mahender, G.; Banerjee, J.; Reddy, M. R. Hypervalent iodinemediated interaction of aldoximes with activated alkenes including Baylis–Hillman adducts: A new and efficient method for the preparation of nitrile oxides from aldoximes. Tetrahedron Lett. 2004, 45, 7347–7350.
    • (2004) Tetrahedron Lett , vol.45 , pp. 7347-7350
    • Das, B.1    Holla, H.2    Mahender, G.3    Banerjee, J.4    Reddy, M.R.5
  • 3
    • 33947688826 scopus 로고    scopus 로고
    • A rapid and efficient synthesis of benzimidazoles using hypervalent iodine as oxidant
    • Du, L.-H.; Wang, Y.-G. A rapid and efficient synthesis of benzimidazoles using hypervalent iodine as oxidant. Synthesis 2007, 675–678.
    • (2007) Synthesis , pp. 675-678
    • Du, L.-H.1    Wang, Y.-G.2
  • 4
    • 0032821239 scopus 로고    scopus 로고
    • Hypervalent iodine compounds: Recent advances in synthetic application
    • Wirth, T.; Hirt, U. H. Hypervalent iodine compounds: Recent advances in synthetic application. Synthesis 1999, 1271–1287.
    • (1999) Synthesis , pp. 1271-1287
    • Wirth, T.1    Hirt, U.H.2
  • 5
    • 0000234498 scopus 로고    scopus 로고
    • A simple and advantageous protocol for the oxidation of alcohols with o-iodoxybenzoic acid (IBX)
    • More, J. D.; Finney, N. A simple and advantageous protocol for the oxidation of alcohols with o-iodoxybenzoic acid (IBX). Org. Lett. 2002, 4(17), 3001–3003.
    • (2002) Org. Lett , vol.4 , Issue.17 , pp. 3001-3003
    • More, J.D.1    Finney, N.2
  • 6
    • 0034829609 scopus 로고    scopus 로고
    • Selective oxidation at carbon adjacent to aromatic systems with IBX
    • Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L. Selective oxidation at carbon adjacent to aromatic systems with IBX. J. Am. Chem. Soc. 2001, 123, 3183–3185.
    • (2001) J. Am. Chem. Soc , vol.123 , pp. 3183-3185
    • Nicolaou, K.C.1    Baran, P.S.2    Zhong, Y.-L.3
  • 7
    • 1942536050 scopus 로고    scopus 로고
    • O-Iodoxybenzoic acid (IBX) as a viable reagent in the manipulation of nitrogen and sulphur containing substrates, scope, generality, and mechanism of IBX-mediated amine oxidations and dithiane deprotections
    • Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. o-Iodoxybenzoic acid (IBX) as a viable reagent in the manipulation of nitrogen and sulphur containing substrates, scope, generality, and mechanism of IBX-mediated amine oxidations and dithiane deprotections. J. Am. Chem. Soc. 2004, 126, 5192–5201.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 5192-5201
    • Nicolaou, K.C.1    Mathison, C.J.N.2    Montagnon, T.3
  • 9
    • 0003134393 scopus 로고
    • Synthesis and reactions of 5-(Tributylstannyl)isoxazoles
    • Kondo, Y.; Uchiyama, D.; Sakamoto, T.; Yamanaka, H. Synthesis and reactions of 5-(tributylstannyl)isoxazoles. Tetrahedron Lett. 1989, 30, 4249–4250.
    • (1989) Tetrahedron Lett , vol.30 , pp. 4249-4250
    • Kondo, Y.1    Uchiyama, D.2    Sakamoto, T.3    Yamanaka, H.4
  • 10
    • 0001291073 scopus 로고
    • Synthesis of isoxazolines and isoxazoles from aldoximes by the use of sodium bromite with organotin halide
    • Morriyo, O.; Nakamura, H.; Kageyama, T.; Urata, Y. Synthesis of isoxazolines and isoxazoles from aldoximes by the use of sodium bromite with organotin halide. Tetrahedron Lett. 1989, 30, 3987–3990.
    • (1989) Tetrahedron Lett , vol.30 , pp. 3987-3990
    • Morriyo, O.1    Nakamura, H.2    Kageyama, T.3    Urata, Y.4
  • 11
    • 0000228798 scopus 로고    scopus 로고
    • Convenient one-pot preparative method for 4,5-diarylisoxazole involving exchange reactions
    • Dominguez, E.; Ibeus, E.; Martinez de Margart, E.; Palacius, J. K.; San Marka, E. A convenient one-pot preparative method for 4,5-diarylisoxazole involving exchange reactions. J. Org. Chem. 1996, 61, 5435–5439.
    • (1996) J. Org. Chem , vol.61 , pp. 5435-5439
    • Dominguez, E.1    Ibeus, E.2    Martinez De Margart, E.3    Palacius, J.K.4    San Marka, E.A.5
  • 13
    • 0037140866 scopus 로고    scopus 로고
    • Heterocyclic nucleoside analogues: Design and synthesis of antiviral, modified nucleosides containing isoxazole heterocycles
    • Lee, Y.-S.; Kim, B. H. Heterocyclic nucleoside analogues: Design and synthesis of antiviral, modified nucleosides containing isoxazole heterocycles. Bioorg. Med. Chem. Lett. 2002, 12, 1395–1397.
    • (2002) Bioorg. Med. Chem. Lett , vol.12 , pp. 1395-1397
    • Lee, Y.-S.1    Kim, B.H.2
  • 14
    • 0032771335 scopus 로고    scopus 로고
    • A novel and convenient method towards synthesis of 3,5-diarylisoxazoles
    • Desai, V. G.; Tilve, S. G. A novel and convenient method towards synthesis of 3,5-diarylisoxazoles. Synth. Commun. 1999, 29(17), 3017–3020.
    • (1999) Synth. Commun , vol.29 , Issue.17 , pp. 3017-3020
    • Desai, V.G.1    Tilve, S.G.2
  • 16
    • 0000567452 scopus 로고
    • Interchange of functionality in conjugated carbonyl compounds through isoxazoles
    • Buchi, G.; Vedera, J. C. Interchange of functionality in conjugated carbonyl compounds through isoxazoles. J. Am. Chem. Soc. 1972, 94, 9128–9132.
    • (1972) J. Am. Chem. Soc , vol.94 , pp. 9128-9132
    • Buchi, G.1    Vedera, J.C.2
  • 17
    • 0026619782 scopus 로고
    • A convenient preparation of 3,5-diarylisoxazoles
    • Wei, X.; Fang, J.; Hu, Y.; Hu, H. A convenient preparation of 3,5-diarylisoxazoles. Synthesis 1992, 1205–1206.
    • (1992) Synthesis , pp. 1205-1206
    • Wei, X.1    Fang, J.2    Hu, Y.3    Hu, H.4
  • 18
    • 84988032470 scopus 로고
    • New method for the synthesis of substituted 3,5-diphenylisoxazoles
    • Balasundaram, B.; Perumal, P. T. A new method for the synthesis of substituted 3,5-diphenylisoxazoles. Synth. Commun. 1990, 20, 293–299.
    • (1990) Synth. Commun , vol.20 , pp. 293-299
    • Balasundaram, B.1    Perumal, P.2
  • 19
    • 84987319156 scopus 로고
    • Reaction of vinyl ketoximes with N-bromosuccinimide: Synthesis of isoxazoles and 4-bromoisoxazolines
    • Hansen, J. F.; Strong, S. A. Reaction of vinyl ketoximes with N-bromosuccinimide: Synthesis of isoxazoles and 4-bromoisoxazolines. J. Heterocycl. Chem. 1977, 14, 1289–1292.
    • (1977) J. Heterocycl. Chem , vol.14 , pp. 1289-1292
    • Hansen, J.F.1    Strong, S.A.2
  • 20
    • 0002966104 scopus 로고
    • Insertion into cyclopropane ring by use of NOBF4 formation of 2-isoxazolines
    • Ichinose, N.; Mizuno, K.; Tamai, T.; Otsuji, Y. A novel NO insertion into cyclopropane ring by use of NOBF4 formation of 2-isoxazolines. Chem. Lett. 1988, 233–236.
    • (1988) Chem. Lett , pp. 233-236
    • Ichinose, N.1    Mizuno, K.2    Tamai, T.3    Otsuji, Y.A.4    Novel, N.O.5
  • 21
    • 84983372540 scopus 로고
    • An improved synthesis of 3,5-disubstitutedisoxazoles and pyrazoles from C(A)o-dithiooximes and C (a), N-dithiophenylhydrazones
    • Fulmer, T. D.; Dasher, L. P.; Bobb, B. L.; Wilson, J. D.; Sides, K. L.; Beam C. F. An improved synthesis of 3,5-disubstitutedisoxazoles and pyrazoles from C(a)o-dithiooximes and C (a), N-dithiophenylhydrazones. J. Heterocycl. Chem. 1980, 17(4), 799–800.
    • (1980) J. Heterocycl. Chem , vol.17 , Issue.4 , pp. 799-800
    • Fulmer, T.D.1    Dasher, L.P.2    Bobb, B.L.3    Wilson, J.D.4    Sides, K.L.5    Beam, C.F.6
  • 22
    • 34047219082 scopus 로고    scopus 로고
    • 3-mediated regioselective synthesis of isoxazoles and pyrazolines
    • Kidwai, M.; Kukreja, S.; Thakur, R. K2CO3-mediated regioselective synthesis of isoxazoles and pyrazolines. Lett. Org. Chem. 2006, 3, 135–139.
    • (2006) Lett. Org. Chem , vol.3 , pp. 135-139
    • Kidwai, M.1    Kukreja, S.2    Thakur, R.3
  • 23
    • 0034551591 scopus 로고    scopus 로고
    • Solid-phase synthesis of isoxazoles and pyrazoles under microwave irradiations
    • Balalaie, S.; Sharifi, A.; Ahangarian, B. Solid-phase synthesis of isoxazoles and pyrazoles under microwave irradiations. Ind. J. Heterocycl. Chem. 2000, 10, 149–150.
    • (2000) Ind. J. Heterocycl. Chem. , vol.10 , pp. 149-150
    • Balalaie, S.1    Sharifi, A.2    Ahangarian, B.3
  • 24
    • 84988032476 scopus 로고    scopus 로고
    • Microwave irradiation synthesis of 3,5-diarylisoxazoles in aqueous solutions
    • Shi, X.-N.; Wang, J.-X. Microwave irradiation synthesis of 3,5-diarylisoxazoles in aqueous solutions. Yingyong Huaxue. 2010, 27(5), 539–543.
    • (2010) Yingyong Huaxue , vol.27 , Issue.5 , pp. 539-543
    • Shi, X.-N.1    Wang, J.-X.2
  • 25
    • 0036992602 scopus 로고    scopus 로고
    • Aqueous one-pot synthesis of pyrazoles, pyrimidines, and isoxazoles promoted by microwave irradiation
    • Molteni, V.; Hamilton, M. M.; Long, M.; Crane, C. M.; Termin, A. P.; Wilson, D. M. Aqueous one-pot synthesis of pyrazoles, pyrimidines, and isoxazoles promoted by microwave irradiation. Synthesis 2002, 1669–1674.
    • (2002) Synthesis , pp. 1669-1674
    • Molteni, V.1    Hamilton, M.M.2    Long, M.3    Crane, C.M.4    Termin, A.P.5    Wilson, D.M.6
  • 26
    • 24944553428 scopus 로고    scopus 로고
    • One-pot copper(I)-catalysed synthesis of 3,5-disubstituted isoxazoles
    • Hansen, T. V.; Wu, P.; Fokin, V. V. One-pot copper(I)-catalysed synthesis of 3,5-disubstituted isoxazoles. J. Org. Chem. 2005, 70(19), 7761–7764.
    • (2005) J. Org. Chem , vol.70 , Issue.19 , pp. 7761-7764
    • Hansen, T.V.1    Wu, P.2    Fokin, V.V.3
  • 27
    • 69449104557 scopus 로고    scopus 로고
    • Efficient and regioselective one-pot synthesis of 3-substituted and 3,5-disubstituted isoxazoles
    • Tang, S.; He, J.; Sun, Y.; She, X. Efficient and regioselective one-pot synthesis of 3-substituted and 3,5-disubstituted isoxazoles. Org. Lett. 2009, 11(17), 3982–3985.
    • (2009) Org. Lett , vol.11 , Issue.17 , pp. 3982-3985
    • Tang, S.1    He, J.2    Sun, Y.3    She, X.4
  • 28
    • 0001424311 scopus 로고
    • New synthesis of isoxazoles from 1,4-dianions of oximes having an a-hydrogen: Mass spectrometry
    • Beam, C. F.; Dyer, M. C. D.; Schwarz, R. A.; Hauser, C. R. New synthesis of isoxazoles from 1,4-dianions of oximes having an a-hydrogen: Mass spectrometry. J. Org. Chem. 1970, 35(6), 1806–1810.
    • (1970) J. Org. Chem , vol.35 , Issue.6 , pp. 1806-1810
    • Beam, C.F.1    Dyer, M.C.D.2    Schwarz, R.A.3    Hauser, C.R.4
  • 29
    • 38849179369 scopus 로고    scopus 로고
    • Novel microwave-assisted one-pot synthesis of isoxazoles by a three-component coupling–cycloaddition sequence
    • Benjamin, W.; Rominger, F.; Muller, T. J. J. Novel microwave-assisted one-pot synthesis of isoxazoles by a three-component coupling–cycloaddition sequence. Synthesis 2008, 293–303.
    • (2008) Synthesis , pp. 293-303
    • Benjamin, W.1    Rominger, F.2    Muller, T.3
  • 30
    • 74049097181 scopus 로고    scopus 로고
    • Synthesis and tuberculosis activity of novel mefloquine isoxazole carboxylic ester as prodrugs
    • Mao, J.; Yuan, H.; Wang, Y.; Wan, B.; Pak, D.; He, R.; Franzblan, S. G. Synthesis and tuberculosis activity of novel mefloquine isoxazole carboxylic ester as prodrugs. Bioorg. Med. Chem. Lett. 2010, 20(3), 1263–1268.
    • (2010) Bioorg. Med. Chem. Lett , vol.20 , Issue.3 , pp. 1263-1268
    • Mao, J.1    Yuan, H.2    Wang, Y.3    Wan, B.4    Pak, D.5    He, R.6    Franzblan, S.G.7
  • 31
    • 0031434549 scopus 로고    scopus 로고
    • Synthesis and biochemical evaluation of N-(4-phenylthiazol-2-yl)benzenesulfonamides as high affinity inhibitor of kynurenine-3-hydroxylase
    • Rover, S.; Cesura, M. A.; Huguenin, P.; Kettler, R.; Szente, A. Synthesis and biochemical evaluation of N-(4-phenylthiazol-2-yl)benzenesulfonamides as high affinity inhibitor of kynurenine-3-hydroxylase. J. Med. Chem. 1997, 40, 4378–4385.
    • (1997) J. Med. Chem , vol.40 , pp. 4378-4385
    • Rover, S.1    Cesura, M.A.2    Huguenin, P.3    Kettler, R.4    Szente, A.5
  • 33
    • 77950863641 scopus 로고    scopus 로고
    • Synthesis of some 5-phenylisoxazole-3-carboxylic acid derivatives as potent xanthine oxidase inhibitors
    • Wang, S.; Yan, J.; Chen, J. Zhang, T.; Zhao, Y.; Xue, M. Synthesis of some 5-phenylisoxazole-3-carboxylic acid derivatives as potent xanthine oxidase inhibitors. Eur. J. Med. Chem. 2010, 45(6), 2663–2670.
    • (2010) Eur. J. Med. Chem , vol.45 , Issue.6 , pp. 2663-2670
    • Wang, S.1    Yan, J.2    Chen, J.3    Zhang, T.4    Zhao, Y.5    Xue, M.6
  • 34
    • 33646079888 scopus 로고    scopus 로고
    • Short and efficient preparations of isoxazole-3-carboxylic acid and imino-oxopentanoic acid potent precursors of 4-hydroxyisoleucine
    • Becht, J.-M.; Maruani, M.; Wagner, A.; Mioskonski, C. Short and efficient preparations of isoxazole-3-carboxylic acid and imino-oxopentanoic acid potent precursors of 4-hydroxyisoleucine. Tetrahedron 2006, 62(18), 4430–4434.
    • (2006) Tetrahedron , vol.62 , Issue.18 , pp. 4430-4434
    • Becht, J.-M.1    Maruani, M.2    Wagner, A.3    Mioskonski, C.4
  • 35
    • 0842341068 scopus 로고
    • Nitrile oxides VIII: Cyanogen N-oxide
    • Grundmann, C. Nitrile oxides VIII: Cyanogen N-oxide. J. Org. Chem. 1966, 31(12), 4235–4237.
    • (1966) J. Org. Chem , vol.31 , Issue.12 , pp. 4235-4237
    • Grundmann, C.1
  • 36
    • 0344179174 scopus 로고
    • A,b-Unsaturated oximes: Isoxazoline formation by thermal cyclisation of compounds related to benzalacetophenone oxime and isoxazoline thermal cycloreversion reactions
    • Shotter, R. G.; Seshadri, D.; Wright, P. H. a,b-Unsaturated oximes: Isoxazoline formation by thermal cyclisation of compounds related to benzalacetophenone oxime and isoxazoline thermal cycloreversion reactions. Tetrahedron 1975, 31, 3069–3072.
    • (1975) Tetrahedron , vol.31 , pp. 3069-3072
    • Shotter, R.G.1    Seshadri, D.2    Wright, P.H.3
  • 37
    • 84987964389 scopus 로고    scopus 로고
    • Synthesis and fungicity of 3,5-disubstituted isoxazoles
    • Babar, L. Synthesis and fungicity of 3,5-disubstituted isoxazoles. Pesticide Res. J. 2005, 17(2), 1–5.
    • (2005) Pesticide Res. J , vol.17 , Issue.2 , pp. 1-5
    • Babar, L.1
  • 38
    • 84988036553 scopus 로고    scopus 로고
    • An insight into general features of IBX (2-iodoxy benzoic acid)
    • Sharma, P.; Kaur, N.; Pareek, A.; Kishore, D. An insight into general features of IBX (2-iodoxy benzoic acid). Sci. Rev. Chem. Commun. 2013, 3(1), 16–42.
    • (2013) Sci. Rev. Chem. Commun , vol.3 , Issue.1 , pp. 16-42
    • Sharma, P.1    Kaur, N.2    Pareek, A.3    Kishore, D.4
  • 39
    • 0037070535 scopus 로고    scopus 로고
    • Iodine(V) reagents in organic synthesis, part 4: O-Iodoxybenzoic acid as a chemospecific tool for single-electron-transferbased oxidation processes
    • Nicolaou, K. C.; Montagnon, T.; Baran, P. S.; Zhong, Y.-L. Iodine(V) reagents in organic synthesis, part 4: o-Iodoxybenzoic acid as a chemospecific tool for single-electron-transferbased oxidation processes. J. Am. Chem. Soc. 2002, 124(10), 2245–2258.
    • (2002) J. Am. Chem. Soc , vol.124 , Issue.10 , pp. 2245-2258
    • Nicolaou, K.C.1    Montagnon, T.2    Baran, P.S.3    Zhong, Y.-L.4
  • 40
    • 0033546262 scopus 로고    scopus 로고
    • User-friendly entry to 2-iodoxybenzoic acid (IBX)
    • Frigerio, M.; Santagostina, M.; Sputore, S. A user-friendly entry to 2-iodoxybenzoic acid (IBX). J. Org. Chem. 1999, 64(12), 4537–4538.
    • (1999) J. Org. Chem , vol.64 , Issue.12 , pp. 4537-4538
    • Frigerio, M.1    Santagostina, M.2    Sputore, S.A.3


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