PDF herunterladen
Synthesis 2012(5): 747-754  
DOI: 10.1055/s-0031-1289675
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Microwave-Assisted Synthesis of 1,3-Disubstituted β-Carbolines from α-(Alkylideneamino)nitriles and Gramine

Julien Letessiera, Heiner Deterta, Katharina Götzb, Till Opatz*a
a Institute for Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
Fax: +49(6131)3922338; e-Mail: opatz@uni-mainz.de;
b Institute for Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany
Weitere Informationen

Publikationsverlauf

Received 28 November 2011
Publikationsdatum:
23. Januar 2012 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

Reaction of deprotonated α-(alkylidenamino)nitriles with gramine in the presence of tributylphosphine furnishes α-substituted imines of tryptophane nitrile. Their subsequent intramolecular cyclization followed by dehydrocyanation and oxidation affords 1,3-disubstituted β-carbolines.

Key words

imines - α-aminonitriles - cyclization - alkaloids - β-carbolines

    References

  • 1 Husson H.-P. In The Alkaloids: Chemistry and Pharmacology   Vol. 26:  Brossi A. Academic Press; New York: 1985.  p.1-51  
    Google Scholar
  • 2 Love B. Top. Heterocycl. Chem.  2006,  2:  93 
    Google Scholar
  • 3 Love BE. Org. Prep. Proced. Int.  1996,  28:  1 
    Google Scholar
  • 4 Rao KV. Cullen WP. Antibiot. Annu.  1959-1960,  950 
    Google Scholar
  • 5 Torreilles J. Guérin M.-C. Previero A. Biochimie  1985,  67:  929 
    Google Scholar
  • 6 Bischler A. Napieralski B. Ber. Dtsch. Chem. Ges.  1893,  26:  1903 
    Google Scholar
  • 7 Pictet A. Spengler T. Ber. Dtsch. Chem. Ges.  1911,  44:  2030 
    Google Scholar
  • 8 Dassonneville B. Witulski B. Detert H. Eur. J. Org. Chem.  2011,  2836 
    Google Scholar
  • 9 Nissen F. Detert H. Eur. J. Org. Chem.  2011,  2845 
    Google Scholar
  • 10 Nissen F. Richard V. Alayrac C. Witulski B. Chem. Commun.  2011,  47:  6656 
    Google Scholar
  • 11 Nissen F. Schollmeyer D. Detert H. Acta Crystallogr., Sect. E  2011,  67:  o1497 
    Google Scholar
  • 12 Shi Z. Cui Y. Jiao N. Org. Lett.  2010,  12:  2908 
    Google Scholar
  • 13 Ding S. Shi Z. Jiao N. Org. Lett.  2010,  12:  1540 
    Google Scholar
  • 14 Zhang H. Larock RC. J. Org. Chem.  2002,  67:  9318 
    Google Scholar
  • 15 Wagner FF. Comins DL. Org. Lett.  2006,  8:  3549 
    Google Scholar
  • 16 Hostyn S. Maes BUW. Van Baelen G. Gulevskaya A. Meyers C. Smits K. Tetrahedron  2006,  62:  4676 
    Google Scholar
  • 17 Verniest G. England D. De Kimpe N. Padwa A. Tetrahedron  2010,  66:  1496 
    Google Scholar
  • 18 Rocca P. Marsais F. Godard A. Queguiner G. Tetrahedron  1993,  49:  3325 
    Google Scholar
  • 19 Opatz T. Synthesis  2009,  1941 
    Google Scholar
  • 20 Meyer N. Werner F. Opatz T. Synthesis  2005,  945 
    Google Scholar
  • 21 Meyer N. Opatz T. Eur. J. Org. Chem.  2006,  3997 
    Google Scholar
  • 22 Werner F. Blank N. Opatz T. Eur. J. Org. Chem.  2007,  3911 
    Google Scholar
  • 23 Bergner I. Opatz T. J. Org. Chem.  2007,  72:  7083 
    Google Scholar
  • 24 Opatz T. Ferenc D. Synthesis  2008,  3941 
    Google Scholar
  • 25 Romek A. Opatz T. Eur. J. Org. Chem.  2010,  5841 
    Google Scholar
  • 26 Boekelheide V. Ainsworth C. J. Am. Chem. Soc.  1950,  72:  2134 
    Google Scholar
  • 27 Satou H, Imamura S, and Kuramoto H. inventors; (Toray Industries, Inc.) Jpn. Kokai Tokkyo Koho  57130972.  ; Chem. Abstr. 1982, 97, 216724
  • 28 Low KH. Magomedov NA. Org. Lett.  2005,  7:  2003 
    Google Scholar
  • 29 Somei M. Karasawa Y. Kaneko C. Chem. Lett.  1980,  813 
    Google Scholar
  • 30 Matsuo J.-i. Tanaki Y. Ishibashi H. Tetrahedron  2008,  64:  5262 
    Google Scholar
  • 31 Huffman RW. Bruice TC. J. Am. Chem. Soc.  1967,  89:  6243 
    Google Scholar
  • 32 Schellenberg KA. J. Biol. Chem.  1965,  240:  1165 
    Google Scholar
  • 33 Schellenberg KA. J. Biol. Chem.  1967,  242:  1815 
    Google Scholar
  • 34 Schellenberg KA. McLean GW. J. Am. Chem. Soc.  1966,  88:  1077 
    Google Scholar
  • 35 Schellenberg KA. McLean GW. Lipton HL. Lietman PS. J. Am. Chem. Soc.  1967,  89:  1948 
    Google Scholar
  • 36 Somei M. Karasawa Y. Kaneko C. Heterocycles  1981,  16:  941 
    Google Scholar
  • 37 Letessier J. Schollmeyer D. Detert H. Opatz T. Acta Crystallogr., Sect. E  2011,  67:  o3435 
    Google Scholar
  • 38 Perrin DD. Armarego WLF. Purification of Laboratory Chemicals   3rd ed.:  Pergamon; Oxford: 1988. 
    Google Scholar
  • 39 Gottlieb HE. Kotlyar V. Nudelman A. J. Org. Chem.  1997,  62:  7512 
    Google Scholar
  • 40 McKay AF. Paris GY. Garmaise DL. J. Am. Chem. Soc.  1958,  80:  6276 
    Google Scholar
  • 41 Bergner I. Opatz T. Synthesis  2007,  918 
    Google Scholar
  • 42 Kurtz P. Disselnkötter H. Liebigs Ann. Chem.  1973,  764:  69 
    Google Scholar
  • 43 Lagriffoul P.-H. Tadros Z. Taillades J. Commeyras A. J. Chem. Soc., Perkin Trans. 2  1992,  1279 
    Google Scholar
  • 44 Dubsky JV. Ber. Dtsch. Chem. Ges.  1916,  49:  1045 
    Google Scholar
  • 45 Paventi M. Edward JT. Can. J. Chem.  1987,  65:  282 
    Google Scholar
  • 47 Sheldrick GM. SHELXL97, Program for Crystal Structure Refinement   University of Göttingen; Göttingen: 1997. 
    Google Scholar
46

CCDC-847261 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.