Download PDF
Synlett 2011(18): 2633-2642  
DOI: 10.1055/s-0031-1289550
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Functionalized Heterocycles by Cyclization Reactions of Oxime and Hydrazone 1,4-Dianions

Tuan Thanh Danga,b, Tung Thanh Danga, Peter Langer*a,c
a Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
b Vietnamese Academy of Science and Technology, 18 Hoang Quoc Viet, Hanoi, Vietnam
c Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: peter.langer@uni-rostock.de;
Further Information

Publication History

Received 1 June 2011
Publication Date:
25 October 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

Oxime and hydrazone 1,4-dianions can be generated in situ by deprotonation with 2 equivalents of n-butyllithium (n-BuLi) or lithium diisopropylamide (LDA). In this account, the development and synthetic applications of one-pot cyclizations of oxime and hydrazone dianions with various electrophiles are highlighted. These reactions provide an efficient synthesis of functionalized isoxazoles, pyrazoles and other heterocycles.

1 Introduction

2 Cyclization Reactions of Oxime 1,4-Dianions

3 Cyclization Reactions of Hydrazone 1,4-Dianions

4 Conclusion

Key words

cyclization - dianions - oximes - hydrazones - pyrazoles - isoxazoles

    References

  • For reviews of dianions, see:
  • 1a Thompson CM. Dianion Chemistry in Organic Synthesis   CRC Press Inc.; Florida: 1994. 
    Google Scholar
  • 1b Thompson CM. Green D. Tetrahedron  1991,  47:  4223 
    Google Scholar
  • 2 For a review of cyclization reactions of dianions, see: Langer P. Freiberg W. Chem. Rev.  2004,  104:  4125 
    Google Scholar
  • 3a Baraldi PG. Barco A. Benetti S. Pollini GP. Simoni D. Synthesis  1987,  857 
    Google Scholar
  • 3b Mares D. Romagnoli C. Tosi B. Benvegn R. Bruni A. Vicentini CB. Fungal Genet. Biol.  2002,  36:  47 
    Google Scholar
  • 4 Grunanger P. The Chemistry of Heterocyclic Compounds   Part 1, Vol. 49:  Vita-Finzi P. John Wiley; New York: 1991. 
    Google Scholar
  • 5a Bailey TR. Diana GD. Kowalczyk PJ. Akullian V. Eissenstat MA. Cutcliffe D. Mallamo JP. Carabateas PM. Pevear DC. J. Med. Chem.  1992,  35:  4628 
    Google Scholar
  • 5b Dannhardt G. Lambrecht D. Laufer S. Mutschler E. Schweiber J. Arch. Pharm. (Weinheim, Ger.)  1995,  328:  437 
    Google Scholar
  • 6 Eicher T. Hauptmann S. The Chemistry of Heterocycles   2nd Ed.:  Wiley-VCH; Weinheim: 2003. 
    Google Scholar
  • 7a Ruano JLG. Martin MR. Tetrahedron  2005,  61:  4363 
    Google Scholar
  • 7b Ziegler CB. Tetrahedron Lett.  1993,  34:  75 
    Google Scholar
  • 7c Kim HJ. Lee JH. Olmstead MM. Kurth MJ.
    J. Org. Chem.  1992,  57:  6513 
    Google Scholar
  • 7d Moore JE. Davies MW. Goodenough KM. Wybrow RAJ. York M. Johnson CN. Harrity JPA. Tetrahedron  2005,  61:  6707 
    Google Scholar
  • 7e Toker JD. Tremblay MR. Jari IK. Anita DW. Zhou B. Paul WJ. Janda KD. J. Org. Chem.  2005,  70:  7810 
    Google Scholar
  • 7f Ruano JLG. Bercial F. Fraile A. Martin MR. Synlett  2002,  73 
    Google Scholar
  • 8 Beam CF. Dyer MCD. Schwarz RA. Hauser CR. J. Org. Chem.  1970,  35:  1806 
    Google Scholar
  • 9 Sandifer RM. Shaffer LM. Hollinger WM. Reames DC. Beam CF. J. Heterocycl. Chem.  1976,  13:  607 
    Google Scholar
  • 10 Barber GN. Olofson RA. J. Org. Chem.  1978,  43:  3015 
    Google Scholar
  • 11 Nitz TJ. Volkots DL. Aldous DJ. Oglesgy RC. J. Org. Chem.  1994,  59:  5828 
    Google Scholar
  • 12 Strekowski L. Lin SY. J. Heterocycl. Chem.  1997,  34:  1625 
    Google Scholar
  • 13 Yamamoto Y. Morita Y. Kikuchi R. Yokoo E. Ohtsuka K. Katoh M. Heterocycles  1989,  29:  1443 
    Google Scholar
  • 14 Dang TT. Albrecht U. Langer P. Synthesis  2006,  2515 
    Google Scholar
  • 15 Griffiths JS. Beam CF. Hauser CR. J. Chem. Soc. C  1971,  974 
    Google Scholar
  • 16 Jarrar AA. Hussein AQ. Madi AS. J. Heterocycl. Chem.  1990,  27:  257 
    Google Scholar
  • 17a Albrecht U. Gerwien K. Langer P. Tetrahedron Lett.  2005,  46:  1017 
    Google Scholar
  • 17b Dang TT. Albrecht U. Gerwien K. Siebert M. Langer P. J. Org. Chem.  2006,  71:  2293 
    Google Scholar
  • 18a van Herk T. Brussee J. van den Nieuwendijk AMCH. van der Klein PAM. Ijzerman AP. Stannek C. Burmeister A. Lorenzen A. J. Med. Chem.  2003,  46:  3945 
    Google Scholar
  • 18b Varano F. Catarzi D. Colotta V. Filacchioni G. Galli A. Costagli C. Carlà V. J. Med. Chem.  2002,  45:  1035 
    Google Scholar
  • 18c Pinna GA. Pirisi MA. Mussino J.-M. Murineddu G. Loriga G. Pau A. Grella GE. Farmaco  2003,  58:  749 
    Google Scholar
  • 19a O’Connor JP. Lysz T. Drugs Today  2008,  44:  693 
    Google Scholar
  • 19b Taeuber U. Drugs Exp. Clin. Res.  1990,  16:  7 
    Google Scholar
  • 19c Murray WV. Hadden SK. J. Org. Chem.  1992,  57:  6662 
    Google Scholar
  • 19d Habeeb AG. Praveen PN. Knaus EE.
    J. Med. Chem.  2001,  44:  3039 
    Google Scholar
  • 19e Liu H. Huang X. Shen JM. Luo X. Li M. Xiong B. Chen G. Shen J. Yang Y. Jiang H. Chen K. J. Med. Chem.  2002,  45:  4816 
    Google Scholar
  • 19f Singh SK. Vobbalareddy S. Shivaramakrishna S. Krishnamraju A. Rajjak SA. Casturi SR. Akhila R. Rao YK. Bioorg. Med. Chem. Lett.  2004,  14:  1683 
    Google Scholar
  • 19g Weber A. Casini A. Heine A. Kuhn D. Sapuran CT. Scozzafava A. Klebe G. J. Med. Chem.  2004,  47:  550 
    Google Scholar
  • 19h Kelsey J. Harris O. Cassin J. Behav. Brain Res.  2009,  203:  304 
    Google Scholar
  • 20 Nicolaou KC. Pratt BA. Arseniyadis S. Wartmann M. O’Brate A. Giannakakou P. ChemMedChem  2006,  1:  41 
    Google Scholar
  • 21a Lamberth C. Heterocycles  2007,  71:  1467 
    Google Scholar
  • 21b Zheng W. Yates SR. Papiernik SK. J. Agric. Food Chem.  2008,  56:  7367 
    Google Scholar
  • 22 Fustero S. Roman R. Sanz-Cervera JF. Simon-Fuentes A. Bueno J. Villanova S. J. Org. Chem.  2008,  73:  8545 
    Google Scholar
  • 23a Humphries PA. Finefield JM. Tetrahedron Lett.  2006,  47:  2443 
    Google Scholar
  • 23b Ranatunge RR. Augustyniak M. Bandarage UK. Earl RA. Ellis JL. Garvey DS. Janero DR. Letts LG. Martino AM. Murty MG. Richardson SK. Schroeder JD. Shumway MJ. Tam SW. Trocha AM. Young DV. J. Med. Chem.  2004,  47:  2180 
    Google Scholar
  • 23c Hernandez S. Moreno I. Martin RS. Gomez G. Herrero MT. Dominguez E. J. Org. Chem.  2010,  75:  434 
    Google Scholar
  • 24 Yoon J.-Y. Lee S.-g. Shin H. Curr. Org. Chem.  2011,  15:  657 
    Google Scholar
  • 25 Matsumura N. Kunugihara A. Yoneda S. Tetrahedron Lett.  1983,  24:  3239 
    Google Scholar
  • 26 Foote RS. Beam CF. Hauser CR. J. Heterocycl. Chem.  1970,  7:  589 
    Google Scholar
  • 27 Beam CF. Reames DC. Harris CE. Dasher LW. Hollinger WM. Yhealy NL. Sandifer RM. J. Org. Chem.  1975,  40:  514 
    Google Scholar
  • 28a Dang TT. Dang TT. Langer P. Tetrahedron Lett.  2007,  48:  3591 
    Google Scholar
  • 28b Dang TT. Dang TT. Fischer C. Goerls H. Langer P. Tetrahedron  2008,  64:  2207 
    Google Scholar
  • 28c Dang TT. Dissertation   Rostock University; Germany: 2009. 
    Google Scholar
  • 29 Mazat CL. Beam CF. Hines MA. Synth. Commun.  1990,  20:  253 
    Google Scholar
  • 30 Matsumura N. Kunugihara A. Yoneda S. Tetrahedron Lett.  1984,  25:  4529 
    Google Scholar