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Synthesis 2004(8): 1187-1194  
DOI: 10.1055/s-2004-822347
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 2,3′-Diindolylmethanes and Substituted Indolo[3,2-b]carbazoles

Niklas Wahlströma,b, Birgitta Stenslandc, Jan Bergman*a,b
a Biosciences at NOVUM, Karolinska Institutet, Department of Organic Chemistry, 14157 Huddinge, Sweden
Fax: +46(8)6081501; e-Mail: jabe@biosci.ki.se;
b Södertörn University College, 14104 Huddinge, Sweden
c Preformulation and Biopharmaceutics, Solid State Analysis/SBBG B314:3, Astrazeneca PAR & D, 15185 Södertälje, Sweden
Weitere Informationen

Publikationsverlauf

Received 11 February 2004
Publikationsdatum:
28. April 2004 (online)

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Abstract

Three different synthetic routes to substituted 2,3′-diindolylmethanes, and the syntheses of substituted indolo[3,2-b]carbazoles are described. The first rigid proof of an acylation in the 2-position of a 1,3-unsubstituted indole is also presented in the form of an X-ray structure.

Key words

bisindoles - acylations - Lewis acids - aryl hydrocarbon receptor - indolo[3,2-b]carbazole

    References

  • 1 Whitlock JP. Annu. Rev. Pharmacol. Toxicol.  1999,  39:  103 
    CrossrefGoogle Scholar
  • 2 Bergman J. Janosik T. Wahlström N. Adv. Heterocycl. Chem.  2001,  80:  1 
    Google Scholar
  • 4 Bergander L. Wahlström N. Alsberg T. Bergman J. Rannug A. Rannug U. Drug Metab. Dispos.  2003,  31:  233 
    CrossrefGoogle Scholar
  • 6 Robinson B. J. Chem. Soc.  1963,  3097 
    Google Scholar
  • 7 Yudina LN. Bergman J. Tetrahedron  2003,  59:  1265 
    CrossrefGoogle Scholar
  • 8 Murakami Y. Takahashi H. Nakazawa Y. Koshimizu M. Watanabe T. Yokoyama Y. Tetrahedron Lett.  1989,  30:  2099 
    CrossrefGoogle Scholar
  • 9 Murakami Y. Watanabe T. Yokoyama Y. Naomachi J. Iwase H. Watanabe N. Morihata M. Okuyama N. Kamakura H. Takahashi T. Atoda H. Tojo T. Morita K. Ishii H. Chem. Pharm. Bull.  1993,  41:  1910 
    Google Scholar
  • 10 Tholander J. Bergman J. Tetrahedron  1999,  55:  6243 
    CrossrefGoogle Scholar
  • 11 Pindur U. Müller J. Arch. Pharm.  1987,  320:  280 
    CrossrefGoogle Scholar
  • 12 Snyder BB. In Handbook of Reagents for Organic Synthesis, Acid and Basic Reagents   Reich JH. Rigby JH. Wiley; Chichester, UK: 1999.  p.137 
    Google Scholar
  • 13 Okauchi T. Itonaga M. Minami T. Owa T. Kitoh K. Yoshino H. Org. Lett.  2000,  2:  1485 
    CrossrefPubMedGoogle Scholar
  • 15 Janosik T. Bergman J. Stensland B. Stålhandske C. J. Chem. Soc., Perkin Trans. 1  2002,  330 
    CrossrefGoogle Scholar
  • 16 Wynberg H. Groen MB. J. Am. Chem. Soc.  1968,  90:  5339 
    CrossrefGoogle Scholar
  • 17 Groen MB. Schadenberg H. Wynberg H. J. Org. Chem.  1971,  36:  2797 
    CrossrefGoogle Scholar
  • 18 Mahboobi S. Teller S. Pongratz H. Hufsky H. Sellmer A. Botzki A. Uecker A. Beckers T. Baasner S. Schaechtele C. Ueberall F. Kassack MU. Dove S. Boehmer F.-D. J. Med. Chem.  2002,  45:  1002 
    CrossrefGoogle Scholar
  • 19 Jackson AH. Prasitpan N. Shannon PVR. Tinker AC. J. Chem. Soc., Perkin Trans. 1  1987,  2543 
    CrossrefGoogle Scholar
  • 20 Budylin VA. Matveeva ED. Kost AN. Khim. Geterotsikl. Soedin.  1980,  16:  1235 
    Google Scholar
  • 21 Gribble GW. Fletcher GL. Ketcha DM. Rajopadhye M. J. Org. Chem.  1989,  54:  3264 
    CrossrefGoogle Scholar
  • 22 Katritzky AR. Akutagawa K. Tetrahedron Lett.  1985,  26:  5935 
    CrossrefGoogle Scholar
  • 23 Romero DL. Morge RA. Biles C. Berrios-Pena N. May PD. Palmer JR. Johnson PD. Smith HW. Busso M. Tan C.-H. Voorman RL. Reusser F. Althaus IW. Downey KM. So AG. Resnik L. Tarpley WG. Aristoff PA. J. Med. Chem.  1994,  37:  999 
    CrossrefGoogle Scholar
  • 24 Tholander J. Ph.D. Thesis   KTH; Stockholm: 1999. 
    Google Scholar
  • 25 Pelaprat D. Oberlin R. Le Guen I. Le Pecq J.-B. Roques BP. J. Med. Chem.  1980,  23:  1330 
    CrossrefGoogle Scholar
  • 26 Heindl J. inventors; Ger. Offen. (Schering A.-G., Fed. Rep. Ger.), CAS 98:89168, DE  3115992. 
  • 27 Repke DB. Grotjahn DB. Shulgin AT. J. Med. Chem.  1985,  28:  892 
    CrossrefGoogle Scholar
  • 28 Tholander J. Bergman J. Tetrahedron  1999,  55:  6243 
    CrossrefGoogle Scholar
  • 29 Allen MS. Hamaker LK. La Loggia AJ. Cook JM. Synth. Commun.  1992,  22:  2077 
    CrossrefGoogle Scholar
  • 30 Yudina LN. Bergman J. Tetrahedron  2003,  59:  1265 
    CrossrefGoogle Scholar
3

Bergander, L.; Rannug, A.; Rannug, U. to be published.

5

Wahlström, N.; Romero, I.; Bergman, J. to be published.

14

The crystallographic data of 7h have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 230285. Copies of the data can be obtained free of charge, e-mail: deposit@ccdc.cam.ac.uk.