Mild and efficient oxidation of 2-pyrazolines and isoxazolines by trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxalane–NH4Cl–HOAc in water–MeCN
详细信息    查看全文
  • 作者:Kaveh Khosravi
  • 关键词:trans ; 3 ; 5 ; Dihydroperoxy ; 3 ; 5 ; dimethyl ; 1 ; 2 ; dioxalane ; 2 ; Pyrazolines ; Isoxazolines ; Pyrazoles ; Isoxazoles ; Ammonium chloride
  • 刊名:Research on Chemical Intermediates
  • 出版年:2015
  • 出版时间:August 2015
  • 年:2015
  • 卷:41
  • 期:8
  • 页码:5253-5260
  • 全文大小:438 KB
  • 参考文献:1.A. Ciupa, P.A. De Bank, M.F. Mahon, P.J. Wood, L. Caggiano, Med. Chem. Commun. 4, 956 (2013)View Article
    2.M. Sechi, L. Sannia, F. Carta, M. Palomba, R. Dallocchio, A. Dessì, M. Derudas, Z. Zawahir, N. Neamati, Antiviral Chem. Chemother. 16, 41 (2005)View Article
    3.S. Rapposelli, A. Lapucci, F. Minutolo, E. Orlandini, G. Ortore, M. Pinza, A. Balsamo II, Farmaco 59, 25 (2004)View Article
    4.B. Cottineau, P. Toto, C. Marot, A. Pipaud, J. Chenault, J. Bioorg, Med. Chem. Lett. 12, 2105 (2002)View Article
    5.P. Cali, L. Naerum, S. Mukhija, A. Hjelmencrantz, Bioorg. Med. Chem. Lett. 14, 5997 (2004)View Article
    6.F. Al-Omran, A.A. El-Khair, J. Heterocycl. Chem. 41, 327 (2004)View Article
    7.Y. Li, H.-Q. Zhang, J. Liu, X.-P. Yang, Z.-J. Liu, J. Agric. Food Chem. 54, 3636 (2006)View Article
    8.T.L. Siddall, D.G. Ouse, Z.L. Benko, G.M. Garvin, J.L. Jackson, J.M. McQuiston, M.J. Ricks, T.D. Thibault, J.A. Turner, J.C. VanHeertum, M.R. Weimer, Pest Manage. Sci. 58, 1175 (2002)View Article
    9.M. Schnürch, R. Flasik, A.F. Khan, M. Spina, M.D. Mihovilovic, P. Stanetty, Eur. J. Org. Chem. 3283 (2006)
    10.L.D. Nunno, A. Scilimati, P. Vitale, Tetrahedron 58, 2659 (2002)View Article
    11.D. Azarifar, M. Shaebanzadeh, Molecules 7, 885 (2002)View Article
    12.W.E. Parham, J.F. Dooley, J. Am. Chem. Soc. 89, 985 (1967)View Article
    13.I. Bhatnagar, M.V. George, Tetrahedron 24, 1293 (1968)View Article
    14.Z.H. Khalil, A.S. Yanni, A.A. Abdel-Hafeze, A.A. Khalaf, J. Ind. Chem. Soc. 67, 821 (1990)
    15.G. Aziz, M.H. Nosseir, N.L. Doss, A.S. Rizk, Ind. J. Chem. 14B, 286 (1967)
    16.A.H. Blatt, J. Am. Chem. Soc. 71, 1861 (1949)View Article
    17.B. Das, B. Veeranjaneyulu, M. Krishnaiah, J. Mol. Catal. A: Chem. 284, 116 (2008)View Article
    18.D. Azarifar, B. Maleki, J. Heterocycl. Chem. 42, 157 (2005)View Article
    19.N. Nakamichi, Y. Kawashita, M. Hayashi, Org. Lett. 4, 3955 (2002)View Article
    20.M. Hayashi, Y. Kawashita, Lett. Org. Chem. 3, 571 (2006)View Article
    21.J.N. Shah, C.K. Shah, J. Org. Chem. 43, 1266 (1978)View Article
    22.W.A.F. Goldstone, R.O.C. Norman, J. Chem. Soc. Chem. Commun. 1536 (1966)
    23.K. Auwers, P. Heimke, Ann. Liebigs. 458, 186 (1927)View Article
    24.L.I. Smith, K.L. Howard, J. Am. Chem. Soc. 65, 159 (1943)View Article
    25.N.K. Kochetkov, S.D. Sokolov, Advances in Heterocyclic Chemistry (Academic Press, New York, 1965), p. 420
    26.R.P. Dodwadmath, T.S. Wheeler, Proc. Indian Acad. Sci. 2A, 438 (1935)
    27.S.P. Singh, D. Kumar, O. Prakash, R.P. Kapoor, Synth. Commun. 27, 2683 (1997)View Article
    28.G. Sabitha, G.S.K. Kumar Reddy, C.S. Reddy, N. Fatima, J.S. Yadav, Synthesis 1267 (2003)
    29.C.J. Easton, G.A. Heath, C.M.M. Hughes, C.K.Y. Lee, G.P. Savage, G.W. Simpson, E.R.T. Tiekink, G.J. Vuckovic, R.D. Webster, J. Chem. Soc. Perkin Trans. 1, 1168 (2001)
    30.W. Ried, R. Lantzsch, Chem. Ber. 102, 378 (1969)View Article
    31.C.P. Chuang, M.C. Jiang, Tetrahedron 45, 11229 (1999)View Article
    32.R.K. Chang, K. Kim, Tetrahedron Lett. 41, 8499 (2000)View Article
    33.L. Bianchi, C. Dell’Erba, F. Gasparrini, M. Novi, G. Petrillo, F. Sancassan, C. Tavani, Arkivoc xi, 142 (2002)
    34.B.-X. Wang, T. He, C. Li, H.-W.L. Hu, Chin. J. Org. Chem. 23, 794 (2003)
    35.A. Bunge, H.-J. Hamann, J. Liebscher, Tetrahedron Lett. 50, 524 (2009)View Article
    36.A. Bunge, H.J. Hamann, E. McCalmont, J. Liebscher, Tetrahedron Lett. 50, 4629 (2009)View Article
    37.B. Das, M. Krishnaiah, B. Veeranjaneyulu, B. Ravikanth, Tetrahedron Lett. 48, 6286 (2007)View Article
    38.K. Jakka, J. Liu, C.G. Zhao, Tetrahedron Lett. 48, 1395 (2007)View Article
    39.J. Selvam, V. Suresh, K. Rajesh, D. Chanti Babu, N. Suryakiran, Y. Venkateswarlu, Tetrahedron Lett. 49, 3463 (2008)View Article
    40.P. Ghorai, P.H. Dussault, Org. Lett. 10, 4577 (2008)View Article
    41.K. Zmitek, K. Zupan, S. Stavber, J. Iskra, J. Org. Chem. 72, 6534 (2007)View Article
    42.D. Azarifar, K. Khosravi, F. Soleimanei, Synthesis 15 (2009)
    43.D. Aarifar, K. Khosravi, Synlett 2755 (2010)
    44.D. Azarifar, K. Khosravi, Eur. J. Chem. 1, 15 (2010)View Article
    45.D. Azarifar, K. Khosravi, Z. Najminejad, Kh Soleimani, J. Iran. Chem. Soc. 9, 321 (2012)View Article
    46.D. Azarifar, Z. Najminejad, K. Khosravi, Synth. Commun. 43, 826 (2013)View Article
    47.M.A. Zolfigol, D. Azarifar, S. Mallakpour, I. Mohammadpoor-Baltork, A. Forghaniha, B. Maleki, M. Abdollahi-Alibeik, Tetrahedron Lett. 47, 833 (2006)View Article
    48.B. Han, Z. Liu, Q. Liu, L. Yang, Z.-L. Liu, W. Yu, Tetrahedron 62, 2492 (2006)View Article
    49.D. Azarifar, M.A. Zolfigol, B. Maleki, Bull. Korean Chem. Soc. 25, 23 (2004)View Article
    50.M.M. Heravi, R. Hekmat-Shoar, L. Pedram, J. Mol. Catal. A: Chem. 231, 89 (2005)View Article
    51.D. Azarifar, A. Gharshasebi, Heterocycles 68, 1209 (2006)View Article
    52.D. Azarifar, B. Maleki, K. Mohammadi, Heterocycles 71, 683 (2007)View Article
    53.L. Chai, Y.
  • 作者单位:Kaveh Khosravi (1)

    1. Department of Chemistry, Faculty of Science, Arak University, 38156-8-8349, Arak, Iran
  • 刊物类别:Chemistry and Materials Science
  • 刊物主题:Chemistry
    Catalysis
    Physical Chemistry
    Inorganic Chemistry
  • 出版者:Springer Netherlands
  • ISSN:1568-5675
文摘
An efficient method has been developed for oxidative aromatization of 2-pyrazolines and isoxazolines into their corresponding 2-pyrazoles and isoxazoles under mild conditions. In this method, trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxalane–NH4Cl–HOAc was used as a novel and effective oxidant in water–MeCN at room temperature with good yields.

© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号

地址:北京市海淀区学院路29号 邮编:100083

电话:办公室:(+86 10)66554848;文献借阅、咨询服务、科技查新:66554700