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Synthesis 2008(20): 3273-3278  
DOI: 10.1055/s-0028-1083152
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Versatile One-Pot Synthesis of β-Carbolines by Reaction of Pyranoindolones with Phenyl- and Benzoylhydrazine

Despina Livadiotou, Dimitra Hatzimimikou, Constantinos Neochoritis, Michael A. Terzidis, Constantinos A. Tsoleridis*, Julia Stephanidou-Stephanatou*
Department of Chemistry, Laboratory of Organic Chemistry, University of Thessaloniki, 54124 Thessaloniki, Macedonia, Greece
Fax: +30(2310)997679; e-Mail: tsolerid@chem.auth.gr; e-Mail: ioulia@chem.auth.gr;
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Publication History

Received 13 June 2008
Publication Date:
25 September 2008 (online)

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Abstract

The synthesis of a number of 2-anilino- and 2-(benzoyl­amino)-β-carbolin-3-ones in good yields by a one-step sequence from the reaction of pyranoindolones with phenylhydrazine or benzoylhydrazine is described; the observed good regioselectivity of the reaction is discussed. Full assignment of all ¹H and ¹³C NMR chemical shifts has been unambiguously achieved.

Key words

benzoylhydrazine - p-benzylic coupling - bisnucleophiles - one-pot reaction - phenylhydrazine - pyranoindoles

    References and notes

  • 1 Allen JRF. Holmstedt B. Phytochemistry  1980,  19:  1573 
    Google Scholar
  • 2a Love BE. Org. Prep. Proced. Int.  1996,  28:  3 
    Google Scholar
  • 2b Magnier E. Langlois Y. Tetrahedron  1998,  54:  6201 
    Google Scholar
  • 2c Nakagawa M. J. Heterocycl. Chem.  2000,  37:  567 
    Google Scholar
  • 2d Cox ED. Diaz-Arauzo H. Huang Q. Reddy MS. Ma C. Harris B. McKernan R. Skolnick P. Cook JM. J. Med. Chem.  1998,  41:  2537 
    Google Scholar
  • 2e Batch A. Dodd RH. J. Org. Chem.  1998,  63:  872 
    Google Scholar
  • 3a Rommelspacher H. May T. Salewsky B. Eur. J. Pharmacol.  1994,  252:  51 
    Google Scholar
  • 3b Kim H. Sablin SO. Ramsay RR. Arch. Biochem. Biophys.  1997,  337:  137 
    Google Scholar
  • 3c Herraiz T. Chaparro C. Biochem. Biophys. Res. Commun.  2005,  326:  378 
    Google Scholar
  • 3d Evans AK. Lowry CA. CNS Drug Rev.  2007,  13:  475 
    Google Scholar
  • 4a Taira Z. Kanzawa S. Dohara C. Ishida S. Matsumoto M. Sakiya Y. Jpn. J. Toxicol. Environ. Health  1997,  43:  83 
    Google Scholar
  • 4b Balón M. Muñoz MA. Carmora C. Guardado P. Galán M. Biophys. Chem.  1999,  80:  41 
    Google Scholar
  • 5 Funayama Y. Nishio K. Wakabayashi K. Nagao M. Shimoi K. Ohira T. Hasegawa S. Saijo N. Mutat. Res.  1996,  349:  183 
    CrossrefGoogle Scholar
  • 6a Cox ED. Cook JM. Chem. Rev.  1995,  95:  1797 
    Google Scholar
  • 6b Yu S. Berner OM. Cook JM. J. Am. Chem. Soc.  2000,  122:  7827 
    Google Scholar
  • 6c Danieli B. Giovanelli P. Lesma G. Passarella D. Saccetti A. Silvani A. J. Comb. Chem.  2005,  7:  458 
    Google Scholar
  • 7 Loew GH. Nienow J. Lawson JA. Toll L. Uyeno ET. Mol. Pharmacol.  1985,  28:  17 
    Google Scholar
  • 8 Barbaccia ML. Ravizza L. Costa E. J. Pharmacol. Exp. Ther.  1986,  236:  307 
    Google Scholar
  • 9 Fuller RW. Wong CJ. Hemrick-Luecke SK. Life Sci.  1986,  38:  409 
    CrossrefGoogle Scholar
  • 10a Pohl B. Luchterhandt T. Bracher F. Synth. Commun.  2007,  37:  1273 
    Google Scholar
  • 10b Lingam Y. Rao DM. Bhowmik DR. Islam A. Synth. Commun.  2007,  37:  4313 
    Google Scholar
  • 11 Teshigawara T. inventors;  JP42008628.  ; Chem. Abstr. 1968, 68, 49580g
  • 12 Plieninger H. Müller W. Weinerth K. Chem. Ber.  1964,  97:  667 
    CrossrefGoogle Scholar
  • 13 Dorofeenko GN. Korobkova VG. Guzhina EA. Chem. Heterocycl. Compd.  1971,  7:  319 
    CrossrefGoogle Scholar
  • 14a Tolkunov SV. Tolkunov VS. Dulenko VI. Chem. Heterocycl. Compd.  2004,  40:  481 
    Google Scholar
  • 14b Tolkunov VS. Vysotsky YB. Gorban OA. Shishkina SV. Shishkin OV. Dulenko VI. Chem. Heterocycl. Compd.  2005,  41:  515 
    Google Scholar
  • 15 Katritzky AR. Shcherbakova IV. J. Heterocycl. Chem.  1996,  33:  2031 
    CrossrefGoogle Scholar
  • 16 Doitsides N. Mentzafos D. Mitkidou S. Terzis A. Stephanidou-Stephanatou J. Synth. Commun.  1995,  25:  1411 
    CrossrefGoogle Scholar
  • 17 Modi SP. Archer S. J. Org. Chem.  1989,  54:  5189 
    CrossrefGoogle Scholar
  • 18 Hatzimimikou D. Livadiotou D. Tsoleridis CA. Stephanidou-Stephanatou J. Synlett  2008,  1773 
    Article in Thieme ConnectGoogle Scholar
  • 19a Diels O. Köllisch A. Chem. Ber.  1911,  44:  266 
    Google Scholar
  • 19b Bennasar M.-L. Juan C. Roca T. Monerris M. Bosch J. Tetrahedron  2001,  57:  10125 
    Google Scholar
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The multiplicities and chemical shifts of the aromatic protons and of some second-order spectra of R² substituent have been confirmed after simulation with program SpinWorks, version 2.5, available from ftp://davinci.chem.umanitoba.ca.