Download PDF
Synthesis 2009(10): 1623-1634  
DOI: 10.1055/s-0028-1088043
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

First Synthesis of 5-Cyanosalicylates by Formal [3+3] Cyclocondensations of 1,3-Bis(silyloxy)-1,3-butadienes

Abdolmajid Riahia,b, Olumide Fatunsina, Mohanad Shkoora, Rüdiger Dedea, Helmut Reinkea, Christine Fischera,b, Peter Langer*a,b
a Institut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany
b Leibniz-Institut für Katalyse, Universität Rostock e.V., Albert Einstein Str. 29a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: peter.langer@uni-rostock.de;
Further Information

Publication History

Received 28 November 2008
Publication Date:
25 March 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

A variety of functionalized benzonitriles were regioselectively prepared by formal [3+3] cyclocondensation of 1,3-bis(silyloxy)-1,3-butadienes with 3-ethoxy- and 3-silyloxy-2-cyano-2-en-1-ones.

Key words

arenes - benzonitriles - cyclizations - regioselectivity - silyl enol ethers

    References

  • 1 Kleemann A. Engel J. Kutscher B. Reichert D. Pharmaceutical Substances: Syntheses, Patents, Applications   4th ed.:  Thieme; Stuttgart: 2001.  p.241, 488, 553, 825, 1154, 1598 
    Google Scholar
  • 2 Ford RE. Knowles P. Lunt E. Marshall SM. Penrose AJ. J. Med. Chem.  1986,  29:  538 
    CrossrefGoogle Scholar
  • 3 Klunder JM. Hargrave KD. West MA. Cullen E. Pal K. J. Med. Chem.  1992,  35:  1887 
    CrossrefPubMedGoogle Scholar
  • 4 Collin S. El Tayar N. van de Waterbeemd H. Moureau F. Vercauteren DP. Durant F. Langlois M. Testa B. Eur. J. Med. Chem.  1989,  24:  163 
    CrossrefGoogle Scholar
  • 5 Benedini F. Bertolini G. Cereda R. Dona G. Gromo G. J. Med. Chem.  1995,  38:  130 
    CrossrefGoogle Scholar
  • 6 Zwaagstra ME. Timmerman H. Tamura M. Tohma T. Wada Y. J. Med. Chem.  1997,  40:  1075 
    CrossrefGoogle Scholar
  • 7 Zwaagstra ME. Timmerman H. Abdoelgafoer RS. Zhang MQ. Eur. J. Med. Chem.  1996,  31:  861 
    CrossrefGoogle Scholar
  • 8 Pires JR. Saito C. Gomes SL. Giesbrecht AM. Amaral ATd. J. Med. Chem.  2001,  44:  3673 
    CrossrefGoogle Scholar
  • 9 Fletcher SR. Burkamp F. Blurton P. Cheng SKF. Clarkson R. O" Connor D. Spinks D. Tudge M. van Niel MB. Patel S. Chapman K. J. Med. Chem.  2002,  45:  492 
    CrossrefPubMedGoogle Scholar
  • 10 Nielsen FE. Jacobsen P. Worsaae A. Arkhammar POG. Wahl P. Hansen JB. Bioorg. Med. Chem. Lett.  2004,  14:  5727 
    CrossrefGoogle Scholar
  • 11 van Zandt MC. Sibley EO. McCann EE. Combs KJ. Flam B. Sawicki DR. Sabetta A. Carrington A. Sredy J. Howard E. Mitschler A. Podjarny AD. Bioorg. Med. Chem.  2004,  12:  5661 
    CrossrefGoogle Scholar
  • 12 Paulini R. Lerner C. Diederich F. Jakob-Roetne R. Zuercher G. Borroni E. Helv. Chim. Acta  2006,  89:  1856 
    CrossrefGoogle Scholar
  • 13 Zanon J. Klapars A. Buchwald SL. J. Am. Chem. Soc.  2003,  125:  2890 
    CrossrefGoogle Scholar
  • 14a Ellis GP. Romney-Alexander TM. Chem. Rev.  1987,  87:  779 
    Google Scholar
  • 14b Sundermeier M. Zapf A. Beller M. Eur. J. Inorg. Chem.  2003,  3513 
    Google Scholar
  • 14c Cassar L. Foà M. Montanari F. Marinelli GP. J. Organomet. Chem.  1979,  173:  335 
    Google Scholar
  • 14d Sakakibara Y. Okuda F. Shimoyabashi A. Kirino K. Sakai M. Uchino N. Takagi K. Bull. Chem. Soc. Jpn.  1988,  61:  1985 
    Google Scholar
  • 14e Sakakibara Y. Ido Y. Sasaki K. Sakai M. Uchino N. Bull. Chem. Soc. Jpn.  1993,  66:  2776 
    Google Scholar
  • 14f Takagi K. Okamoto T. Sakakibara Y. Oka S. Chem. Lett.  1973,  471 
    Google Scholar
  • 14g Sekiya A. Ishikawa N. Chem. Lett.  1975,  277 
    Google Scholar
  • 14h Takagi K. Okamoto T. Sakakibara Y. Ohno A. Oka S. Hayama N. Bull. Chem. Soc. Jpn.  1975,  48:  3298 
    Google Scholar
  • 14i Dalton JR. Regen SL. J. Org. Chem.  1979,  44:  4443 
    Google Scholar
  • 14j Akita Y. Shimazaki M. Ohta A. Synthesis  1981,  974 
    Google Scholar
  • 14k Chatani N. Hanafusa T. J. Org. Chem.  1986,  51:  4714 
    Google Scholar
  • 14l Takagi K. Sasaki K. Sakakibara Y. Bull. Chem. Soc. Jpn.  1991,  64:  1118 
    Google Scholar
  • 14m Anderson Y. Långström B. J. Chem. Soc., Perkin Trans. 1  1994,  1395 
    Google Scholar
  • 14n Anderson BA. Bell EC. Ginah FO. Harn NK. Pagh KM. Wepsiec JP. J. Org. Chem.  1998,  63:  8224 
    Google Scholar
  • 14o Okano T. Kiji J. Toyooka Y. Chem. Lett.  1998,  425 
    Google Scholar
  • 14p Maligres PE. Waters MS. Fleitz F. Askin D. Tetrahedron Lett.  1999,  40:  8193 
    Google Scholar
  • 14q Jin F. Confalone PN. Tetrahedron Lett.  2000,  41:  3271 
    Google Scholar
  • 14r Sundermeier M. Zapf A. Beller M. Sans J. Tetrahedron Lett.  2001,  42:  6707 
    Google Scholar
  • 14s Ramnauth J. Bhardwaj N. Renton P. Rakhit S. Maddaford S. Synlett  2003,  2237 
    Google Scholar
  • 14t Sundermeier M. Zapf A. Mutyala S. Baumann W. Sans J. Weiss S. Beller M. Chem. Eur. J.  2003,  9:  1828 
    Google Scholar
  • 14u Sundermeier M. Zapf A. Beller M. Angew. Chem. Int. Ed.  2003,  42:  1661 
    Google Scholar
  • 14v Sundermeier J. Mutyala S. Zapf A. Spannenberg A. Beller M. J. Organomet. Chem.  2003,  684:  50 
    Google Scholar
  • 14w Schareina T. Zapf A. Beller M. Chem. Commun.  2004,  1388 
    Google Scholar
  • 15 Houben J. Fischer W. Chem. Ber.  1933,  66:  339 
    Google Scholar
  • 16a Takashi Y. Shigeki N. Toshiyuki O. Toyoo N. Masateru K. Chem. Pharm. Bull.  1984,  32:  4466 
    Google Scholar
  • 16b van Zandt MC. Sibley EO. McCann EE. Combs KJ. Flam B. Sawicki DR. Sabetta A. Carrington A. Sredy J. Howard E. Mitschler A. Podjarny AD. Bioorg. Med. Chem.  2004,  12:  5661 
    Google Scholar
  • 17a Nelson PH. Carr SF. Devens BH. Eugui EM. Franco F. J. Med. Chem.  1996,  39:  4181 
    Google Scholar
  • 17b Srivastava RR. Collibee SE. Tetrahedron Lett.  2004,  45:  8895 
    Google Scholar
  • 18 Kopp F. Wunderlich S. Knochel P. Chem. Commun.  2007,  20:  2075 
    Google Scholar
  • 19a Taylor EC. Katz AH. McKillop A. Tetrahedron Lett.  1984,  25:  5473 
    Google Scholar
  • 19b Sargent MV. J. Chem. Soc., Perkin Trans. 1  1987,  231 
    Google Scholar
  • 20a Schmidt H.-W. Junek H. Liebigs Ann. Chem.  1979,  2005 
    Google Scholar
  • 20b Schmidt H.-W. Klade M. Liebigs Ann. Chem.  1988,  257 
    Google Scholar
  • 21 Leaver D. Vass JDR. J. Chem. Soc.  1965,  1629 
    CrossrefGoogle Scholar
  • 22 Baker SR. Crombie L. Dove RV. Slack DA. J. Chem. Soc., Perkin Trans. 1  1979,  677 
    Google Scholar
  • See for example:
  • 23a Dilthey W. Schommer W. Trösken O. Chem. Ber.  1933,  66:  1627 
    Google Scholar
  • 23b Noland WE. Kuryla WC. Lange RF. J. Am. Chem. Soc.  1959,  81:  6010 
    Google Scholar
  • 23c Boulton AJ. Mathur SS. J. Org. Chem.  1973,  38:  1054 
    Google Scholar
  • 23d Ciganek E. J. Org. Chem.  1969,  34:  1923 
    Google Scholar
  • 23e Hopf H. Lenich T. Chem. Ber.  1974,  107:  1891 
    Google Scholar
  • 23f Sasaki T. Ishibashi Y. Ohno M. J. Chem. Res., Miniprint  1984,  7:  1972 
    Google Scholar
  • 24 Barbero A. Pulido FJ. Synthesis  2004,  401 
    Article in Thieme ConnectGoogle Scholar
  • 25 Fatunsin O. Shkoor M. Riahi A. Dede R. Reinke H. Langer P. Synlett  2009,  201 
    Article in Thieme ConnectGoogle Scholar
  • 26 For the first [3+3] cyclizations of 1,3-bis(silyloxy)-1,3-butadienes, see: Chan T.-H. Brownbridge P. J. Am. Chem. Soc.  1980,  102:  3534 
    CrossrefGoogle Scholar
  • 27 For a review of [3+3] cyclizations of 1,3-bis(silyloxy)-1,3-butadienes, see: Feist H. Langer P. Synthesis  2007,  327 
    Article in Thieme ConnectGoogle Scholar
  • 28 For a review of 1,3-bis(silyloxy)-1,3-butadienes in general, see: Langer P. Synthesis  2002,  441 
    Article in Thieme ConnectGoogle Scholar
  • 29 Salon J. Milata V. Pronayova N. Lesko J. Monatsh. Chem.  2000,  131:  293 
    CrossrefGoogle Scholar
  • 30a Brownbridge P. Chan TH. Brook MA. Kang GJ. Can. J. Chem.  1983,  61:  688 
    Google Scholar
  • 30b Hirai K. Ojima I. Tetrahedron Lett.  1983,  24:  785 
    Google Scholar
  • 32 Buttke K. Niclas H.-J. Synth. Commun.  1994,  24:  3241 
    CrossrefGoogle Scholar
31

CCDC-716950 contain all crystallographic details of this publication and is available free of charge at: www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK; Fax: +44(1223)336033, or deposit@ccdc.cam.ac.uk.