Download PDF
Synthesis 2010(16): 2725-2730  
DOI: 10.1055/s-0030-1258149
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

The Sandmeyer Reaction on Some Selected Heterocyclic Ring Systems: Synthesis of Useful 2-Chloroheterocyclic-3-carbonitrile Intermediates

Daniel da Silvaa,b, Abdelouahid Samadi*a, Mourad Chiouaa, Maria do Carmo Carreirasb, José Marco-Contelles*a
a Laboratorio de Radicales Libres y Química Computacional (LRL/QC), IQOG (CSIC), C/Juan de la Cierva 3, 28006 Madrid, Spain
Fax: +33(91)5622900; Fax: +34(91)5644853; e-Mail: samadi@iqog.csic.es; e-Mail: iqoc21@iqog.csic.es;
b iMEd.UL, Research Institute for Medicines and Pharmaceutical Sciences, Fac. Pharmacy, Univ. Lisbon, Av. Forças Armadas, 1600-083 Lisbon, Portugal
Further Information

Publication History

Received 30 March 2010
Publication Date:
07 July 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

The Sandmeyer reaction on some selected heterocycles bearing the 2-amino-3-carbonitrile structural moiety has been investigated in order to prepare the corresponding 2-chloro-3-carbo­nitrile derivatives as synthetic useful intermediates for further development.

Key words

Sandmeyer reaction - 2-amino(heterocyclic)-3-carbo­nitriles - 2-aminopyrazoles - 2-aminooxazoles - 2-amino-4H-pyrans - 2-amino-1,4-dihydropyridines - 2-aminopyridines - 2-chloro(heterocyclic)-3-carbonitriles

    References

  • 1 Chioua M. Samadi A. Soriano E. Lozach O. Meijer L. Marco-Contelles J. Bioorg. Med. Chem. Lett.  2009,  19:  4566 
    CrossrefSearch in Google Scholar
  • 2a Hodgson HH. Chem. Rev.  1947,  40:  251 
    Search in Google Scholar
  • 2b Merkushev EB. Synthesis  1988,  923 
  • 3 Troschütz R. Karger A. J. Heterocyl. Chem.  1996,  33:  1815 
    CrossrefSearch in Google Scholar
  • 4 Elkasaby MA. Elshahed F. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1981,  20:  428 
    Search in Google Scholar
  • 5a 3-Chloroquinoxaline-2-carbonitrile: Ortega MA. Montoya ME. Zarranz B. Jaso A. Aldana I. Leclerc S. Meijer L. Monge A. Bioorg. Med. Chem. Lett.  2002,  10:  2177 
    Search in Google Scholar
  • 5b 2,6-Dichloro-5-fluoronicotinonitrile: Repine JT. Johnson DS. Stuk T. White AD. Stier MA. Li T. Yang Z. Maiti SN. Tetrahedron Lett.  2007,  48:  8189 
    Search in Google Scholar
  • 5c 2-Chloro-6-methoxy-4-phenylpyridine-3,5-dicarbo-nitrile: Quintela JM. Soto JL. An. Quim.  1984,  80:  268 
    Search in Google Scholar
  • For the synthesis and reactivity of related ethyl 4-aryl-6-chloro-5-formyl-2-methyl-1,4-dihydropyridine-3-carbox-ylates, see:
  • 6a Verdecia Y. Suárez M. Morales A. Rodríguez E. Ochoa E. González L. Martín N. Quinteiro M. Seoane C. Soto JL. J. Chem. Soc., Perkin Trans. 1  1996,  947 
  • 6b See also: Ojea V. Peinador C. Quintela JM. Synthesis  1992,  798 
  • 7 Doyle MP. Siegfried B. Dellaria JF. J. Org. Chem.  1977,  42:  2426 
    CrossrefSearch in Google Scholar
  • 8 Kochi JK. J. Am. Chem. Soc.  1957,  79:  2942 
    CrossrefSearch in Google Scholar
  • 9 Dickenson CL. Williams JK. McKusick BC. J. Org. Chem.  1964,  29:  1915 
    CrossrefSearch in Google Scholar
  • 10 Freeman F. Kim Darrick SHL. Tetrahedron Lett.  1989,  30:  2631 
    CrossrefSearch in Google Scholar
  • 11 León R. Marco-Contelles J. García AG. Villarroya M. Bioorg. Med. Chem.  2005,  13:  1167 
    CrossrefSearch in Google Scholar
  • 12 Srivastava S. Batra S. Bhaduri AP. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1996,  35:  602 
    Search in Google Scholar
  • 13 Marco-Contelles J. Leon R. de los Ríos C. Samadi A. Bartolini M. Andrisano V. Huertas O. Barril X. Luque FJ. Rodríguez-Franco MI. Lopez B. López MG. García AG. Carreiras MC. Villarroya M. J. Med. Chem.  2009,  52:  2724 
    CrossrefPubMedSearch in Google Scholar
  • 14 Marco JL. de los Ríos C. García AG. Villarroya M. Carreiras MC. Martins C. Eleuterio A. Morreale A. Orozco M. Luque FJ. Bioorg. Med. Chem.  2004,  12:  2199 
    CrossrefSearch in Google Scholar
  • 15 Elkasaby MA. Elshahed F. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1981,  20:  428 
    Search in Google Scholar
  • 16 León R. Marco-Contelles J. García AG. Villarroya M. Bioorg. Med. Chem.  2005,  13:  1167 
    CrossrefSearch in Google Scholar
  • 17 Goldfarb DS. inventors; US Patent  2009163545.  ; Chem. Abstr. 2009, 151, 92842
  • 18 Zhao C. Tovar C. Yin X. Xu Q. Todorov IT. Vassilev LT. Chen L. Bioorg. Med. Chem. Lett.  2009,  19:  319 
    CrossrefSearch in Google Scholar
  • 19 Girgis NS. Pedersen EB. Synthesis  1985,  547 
    Thieme Connect
  • 20 Elsinghorst PW. Haertig W. Goldhammer S. Grosche J. Gütschow M. Org. Biomol. Chem.  2009,  7:  3940 
    CrossrefSearch in Google Scholar