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Reakcja Niementowskiego

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Warianty tytułu
EN
The Niementowski reaction
Języki publikacji
PL
Abstrakty
EN
The Niementowski reaction depends on the fusion of anthranilic acid with carbonyl compounds or amides and dates back to the end of the nineteenth century. Numerous variations of the reaction components and modifications of the reaction conditions have appeared in the literature through years. Besides anthranilic acid other synthons including: methyl o-aminobenzoate [25], o-nitrobenzoic acid [26], o-acylaminobenzamide [21], o-aminobenzamide [27], o-aminobenzonitrile [28], isatoic anhydride [29], benzoxasinone [30, 31] have been employed as well. Replacement of the amide component with either amine [9, 32], nitrile [33], imidate [34], thioamide [35], amidine [36], aldehyde [37] or carboxylic acid [28] have also been reported. To increase yield and to reduce the reaction time a number of variables in reaction conditions have been investigated. The best results have been achieved by implementation of a microwave irradiation [38]. The Niementowski reaction and its variants have found widespread use in pharmaceutical and agrochemical fields for the synthesis of compounds containing quinoline and quinazoline systems which are present in a number of natural and synthetic alkaloids [12, 13] and many drugs [1–5].
Rocznik
Strony
369--390
Opis fizyczny
Bibliogr. 59 poz., schem.
Twórcy
  • Zakład Chemii Bioorganicznej, Wydział Farmaceutyczny, Uniwersytet Medyczny w Łodzi, ul. Muszyńskiego 1, 90-151 Łódź
  • Zakład Chemii Bioorganicznej, Wydział Farmaceutyczny, Uniwersytet Medyczny w Łodzi, ul. Muszyńskiego 1, 90-151 Łódź
Bibliografia
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  • [2] R. Kharb, H. Kaur, Int. Res. Pharm., 2013, 4, 63.
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  • [4] R. Arora, A. Kapoor, N.S. Gill, A.C. Rana, Int. Res. J. Pharm., 2011, 12, 22.
  • [5] L. He, H. Li, J. Chen, X.-F. Wu, RSC Adv., 2014, 4, 12065.
  • [6] M.I. El-Gamal, M.A. Khan, M.S. Abdel-Maksoud, M.M.G El-Din, Ch.-H. Oh, Eur. J. Med. Chem., 2014, 87, 484.
  • [7] M.V.N. de Souza, K.C. Pais, C.R. Kaiser, M.A. Peralta, M. de L. Ferreira, M.C.S. Lourenco, Bioorg. Med. Chem., 2009, 17, 1474.
  • [8] S.S. Laddha, S.G. Wadodkar, S.K. Meghal, Arkivoc, 2006, xi, 1.
  • [9] R.S. Giri, H.M. Thaker, T. Giordano, J. Williams, D. Rogers, V. Sudersanam, K.K. Vasu, Eur. J. Med. Chem., 2009, 44, 2184.
  • [10] R. Musiol, M. Serda, S. Hensel-Bielowka, J. Polanski, Curr. Med. Chem., 2010, 17, 1960.
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  • [12] J.P. Michael, Nat. Prod. Rep., 2002, 19, 742.
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  • [14] S. Niementowski, Ber., 1894, 27, 1394.
  • [15] S. von Niementowski, B. Orzechowski, Ber., 1895, 28, 2809.
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  • [17] Z.H Skraup, Monatsh. Chem. 1881, 2, 139.
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  • [21] V.S. Patel, S.R. Patel, J. Indian Chem. Soc., 1965, 42, 531.
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  • [23] R.J. Chong, M.A. Siddiqui, V. Snieckus, Tetrahedron Lett., 1986, 27, 5323.
  • [24] M.-X. Wang, Y. Liu, Z.-T. Huang, Tetrahedron Lett., 2001, 42, 2553.
  • [25] J.F. Meyer, E.C. Wagner, J. Org. Chem., 1943, 8, 239.
  • [26] S.K. Kundu, M.P.D. Mahindaratne, M.V. Quintero, A. Bao, G.R. Negrete, Arkivoc, 2008, ii, 33.
  • [27] Y. Kabri, A. Gellis, P. Vanelle, Green Chem., 2009, 11, 201.
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  • [32] A.R. Khosropour, I. Mohammadpoor-Baltork, H. Ghorbankhani, Tetrahedron Lett., 2006, 47, 3561.
  • [33] M.T. Bogert, A.H. Gotthelf, J. Am. Chem. Soc., 1900, 22, 129.
  • [34] D.J. Connolly, P.J. Guiry, Synlett, 2001, 26, 1707.
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  • [36] J.F. Meyer, E.C. Wagner, J. Org. Chem., 1943, 8, 239.
  • [37] M. Bakavoli, O. Sabzevari, M. Rahimizadeh, Chin. Chem. Lett., 2007, 18, 1466.
  • [38] F.-R. Alexandre, A. Berecibar, T. Besson, Tetrahedron Lett., 2002, 43, 3911.
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  • [41] Y. Seimbille, M.E. Phelps. J. Czernin. D.H.S. Silverman, J. Label. Compd. Radiopharm., 2005, 48, 829.
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  • [49] J.J. Li, Name Reaction for Heterocycylic Chemistry II, Jonh Wiley and Sons, NY, 2011, s. 381.
  • [50] S.S. Laddha, S.P. Bhatnagar, Arkivoc, 2007, xvi, 1.
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  • [59] H.S. Ban, T. Usui, W. Nabeyama, H. Morita, K. Fukuzawa, H. Nakamura, Org. Biomol. Chem., 2009, 7, 4415.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-23c70644-30ae-4b29-b366-a9b5449a9833
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