PDF herunterladen
Synthesis 2002(13): 1871-1878
DOI: 10.1055/s-2002-33909
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Synthetic Route to Hexahydro[1,4]oxazino[2,3-h] and [3,2-j]β-Carboline Derivatives

Stanislas Mayer, Benoît Joseph, Gérald Guillaumet, Jean-Yves Mérour*
Institut de Chimie Organique et Analytique, UMR CNRS 6005, Université d’Orléans, BP 6759, 45067 Orléans Cedex 2, France
Fax: +33(2)38417281; e-Mail: jean-yves.merour@univ-orleans.fr ;
Weitere Informationen

Publikationsverlauf

Received 6 May 2002
Publikationsdatum:
09. September 2002 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

Convenient methods for the regioselective formylation of tetrahydro[1,4]oxazino[2,3-f] and [3,2-g]indole derivatives 3 and 4 are described. The obtained formyl derivatives 6 and 8 were further transformed in four steps into the unknown hexahydro[1,4]oxazino[2,3-h] 1 and [3,2-j]β-carbolines 2.

Key words

oxazinoindoles - regioselective formylation - Vilsmeier-Haack reaction - Rieche reaction

    References

  • 1 Mayer S. Joseph B. Guillaumet G. Mérour J.-Y. Eur. J. Org. Chem.  2002,  1646 
    CrossrefGoogle Scholar
  • 2 Hulkenberg A, and Van Wijingaarden I. inventors; Eur. Patent,  357122.  ; Chem. Abstr. 1970, 113, 152386
  • 3a Ennis MD. Baze ME. Smith MW. Lawson CF. McCall RB. Lahti RA. Piercey MF. J. Med. Chem.  1992,  35:  3058 
    Artikel in Thieme ConnectGoogle Scholar
  • 3b Andrew M. Birch AM. Bradley PA. Synthesis  1999,  1181 
    Artikel in Thieme ConnectGoogle Scholar
  • 4 Mewshaw RE. Marquis KL. Shi X. McGaughey G. Stack G. Webb MB. Abou Gharbia M. Wasik T. Scerni R. Spangler T. Brennan JA. Mazandarini HJ. Coupet J. Andree TH. Tetrahedron  1998,  54:  7081 
    CrossrefGoogle Scholar
  • 5a Sundberg RJ. Indoles   Academic Press; London: 1996.  p.113-116  
    CrossrefGoogle Scholar
  • 5b Desarbre E. Bergman J. J. Chem. Soc., Perkin Trans. 1  1998,  2009 
    CrossrefGoogle Scholar
  • 5c Semmelhack MF. Tetrahedron Lett.  1993,  34:  1395 
    CrossrefGoogle Scholar
  • 6 Cotterill AS. Moody CJ. Roffey JRA. Tetrahedron  1995,  51:  7223 
    CrossrefGoogle Scholar
  • 7a Black DStC. Kumar N. Wong LCH. Synthesis  1986,  474 
    CrossrefPubMedGoogle Scholar
  • 7b Black DStC. Keller P. Kumar N. Aust. J. Chem.  1993,  46:  843 
    CrossrefPubMedGoogle Scholar
  • 7c Black DStC. Kumar N. Mitchell PSR. J. Org. Chem.  2002,  67:  2464 
    CrossrefPubMedGoogle Scholar
  • 8a Partsvaniya DA. Akhvlediani RN. Zhigachev VE. Gordeev EN. Kuleshova LN. Suvorov NN. Khim. Geterotsikl. Soedin.  1986,  22:  1624 ; Chem. Abstr. 1988, 108, 5930
    Google Scholar
  • 8b Partsvaniya DA. Akhvlediani RN. Gordeev EN. Vigdorchik MM. Kuleshova NN. Trubitsyna TK. Mashkovski MD. Suvorov NN. Khim. Farm. Zh.  1986,  20:  1454 ; Chem. Abstr. 1987, 106, 196345
    Google Scholar
  • 9 Fujisawa T. Sato T. Org. Synth.  1987,  66:  121 
    Google Scholar
  • 10 Tani M. Aoki T. Ito S. Matsumoto S. Hideshima M. Fukushima K. Nozawa R. Maede T. Tashiro M. Chem. Pharm. Bull.  1990,  38:  3261 
    Google Scholar
  • 11 1-Dimethylamino-2-nitroethene failed to react with 3 or 4 to give 9 or 12 according to Severin’s method: Severin T. Brück B. Chem. Ber.  1965,  98:  3847 
    Google Scholar
  • 12 Sinhababu AK. Borchardt RT. Tetrahedron Lett.  1983,  24:  227 
    CrossrefGoogle Scholar
13

Compound 6a (n = 1, R = H) could be also transformed into the corresponding nitroethyl derivative of type 10 in a total yield of 69%. Hydrogenation over Raney nickel afforded the ethylamine derivative as a relatively stable solid (mp 103-105 °C; 84% yield), which upon heating in toluene afforded the corresponding lactam of the type 11 in only 34% yield. (DBU gave only degradation products).