Download PDF
Synthesis 2009(18): 3051-3060  
DOI: 10.1055/s-0029-1216919
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Studies on the Chemistry of 2-[3-(2-Nitrophenyl)-2-oxopropyl]benzaldehydes: Novel Syntheses of 5H-Benzo[b]carbazole-6,11-diones and Indolo[1,2-b]isoquinoline-6,11-diones

Marcos Fernández
Hospital Materno-Infantil, Xubias de Arriba s/n, 15006 A Coruña, Spain
Fax: +34(981)178144; e-Mail: Marcos.Fernandez.Villar@sergas.es;
Further Information

Publication History

Received 10 February 2009
Publication Date:
23 July 2009 (online)

    Permissions and Reprints All articles of this category

Corrected by:

Studies on the Chemistry of 2-[3-(2-Nitrophenyl)-2-oxopropyl]benzaldehydes: Novel Syntheses of 5H-Benzo[b]carbazole-6,11-diones and Indolo[1,2-b]- isoquinoline-6,11-dionesSynthesis 2010; 2010(14): 2495-2495
DOI: 10.1055/s-0029-1218838

Abstract

Syntheses of 5H-benzo[b]carbazole-6,11-diones and indolo[1,2-b]isoquinoline-6,11-diones are described. Both compounds are synthesized from 2-[3-(2-nitrophenyl)-2-oxopropyl]benzaldehydes, which were obtained from commercially available indan-1-ones in six steps.

Key words

ozonolysis - ketoaldehyde - aldol condensation - hydrogenation - indole

    References

  • 1 Taylor DA. Mehdi Baradarani M. Martínez SJ. Joule JA. J. Chem. Res., Synop.  1979,  387 ; J. Chem. Res., Miniprint 1979, 4801
    Google Scholar
  • 2 Biochemistry of Quinones   Morton RA. Academic Press; New York: 1965. 
    Google Scholar
  • 3 Bernardo PH. Chai CLL. Le Guen M. Smith GD. Waring P. Bioorg. Med. Chem. Lett.  2007,  17:  82 
    CrossrefGoogle Scholar
  • 4a Cheng CC. Progress in Medicinal Chemistry   Vol. 25:  Ellis GP. West GB. Elsevier; Amsterdam: 1988. 
    Google Scholar
  • 4b Asche C. Frank W. Albert A. Kucklaender U. Bioorg. Med. Chem.  2005,  13:  819 
    Google Scholar
  • 5a Luo Y.-L., Chou T.-C., Cheng C. C.; J. Heterocycl. Chem.; 1996, 33: 113
  • 5b Mocellin S.; Microarray Technology and Cancer Gene Profiling; Springer: Heidelberg, 2007; Chap. 8, 98
  • 6a Bennasar M.-Ll. Roca T. Ferrando F. J. Org. Chem.  2005,  70:  9077 
    Google Scholar
  • 6b Bernardo PH. Chai CLL. Heath GA. Mahon PJ. Smith GD. Waring P. Wilkes BA. J. Med. Chem.  2004,  47:  4958 
    Google Scholar
  • 6c Mal D. Senapati BK. Pahari P. Tetrahedron  2007,  63:  3768 
    Google Scholar
  • 6d Ashcroft WR. Dalton L. Beal MG. Humphrey GL. Joule JA. J. Chem. Soc., Perkin Trans. 1  1983,  2409 
    Google Scholar
  • 7a Hagelin H. Oslob JD. Akermark B. Chem. Eur. J.  1999,  5:  2413 
    Google Scholar
  • 7b Knoelker H.-J. O’Sullivan N. Tetrahedron  1994,  50:  10893 
    Google Scholar
  • 7c O’Sullivan PJ. Moreno R. Murphy WS. Tetrahedron Lett.  1992,  33:  535 
    Google Scholar
  • 7d Bittner S. Krief P. Massil T. Synthesis  1991,  215 
    Google Scholar
  • 8 Fernández M. Barcia C. Estévez JC. Estévez RJ. Castedo L. Synlett  2004,  267 
    Article in Thieme ConnectGoogle Scholar
  • 9a Cruces J. Martínez E. Treus M. Martínez LA. Estévez JC. Estévez RJ. Castedo L. Tetrahedron  2002,  58:  3015 
    Google Scholar
  • 9b Estévez JC. Estévez RJ. Castedo L. Tetrahedron Lett.  1993,  34:  6479 
    Google Scholar
  • 10 Cruces J. Estévez JC. Castedo L. Estévez RJ. Tetrahedron Lett.  2001,  42:  4825 
    CrossrefGoogle Scholar
  • 11 Barcia JC. Cruces J. Estévez JC. Estévez RJ. Castedo L. Tetrahedron Lett.  2002,  43:  5141 
    CrossrefGoogle Scholar
  • 12a Gribble GW. Saulnier MG. Obaza-Nutaitis JA. Ketcha DM. J. Org. Chem.  1992,  57:  5891 
    Google Scholar
  • 12b Merour JY. Piroelle S. Cossais F. Heterocycles  1993,  36:  1287 
    Google Scholar
  • 12c Fraser HL. Gribble GW. Can. J. Chem.  2001,  79:  1515 
    Google Scholar
  • 14a Hooper M. Pitkethly WN. J. Chem. Soc., Perkin Trans. 1  1972,  1607 
    Google Scholar
  • 14b Rajeswaran WG. Srinivasan PC. Synthesis  1994,  270 
    Google Scholar
  • 14c Bennasar M.-L. Roca T. Ferrando F. Tetrahedron Lett.  2004,  45:  5605 
    Google Scholar
  • 15 Nieman JA. Keay BA. Tetrahedron: Asymmetry  1995,  6:  1575 
    CrossrefGoogle Scholar
  • 16 Campbell N. Davison PS. Heller HG. J. Chem. Soc.  1963,  993 
    CrossrefGoogle Scholar
  • 17 Kometani T. Yoshii E. J. Chem. Soc., Perkin Trans. 1  1981,  1191 
    CrossrefGoogle Scholar
  • 18 Ko K.-Y. Eliel EL. J. Org. Chem.  1986,  51:  5353 
    CrossrefGoogle Scholar
  • 19 Martínez A. Fernández M. Estévez JC. Estévez RJ. Castedo L. Tetrahedron  2005,  61:  1353 
    CrossrefGoogle Scholar
  • 20 Wolinsky J. Slabaugh MR. Gibson T. J. Org. Chem.  1964,  29:  3740 
    CrossrefGoogle Scholar
  • 21 Barton DHR. Brewster AG. Ley SV. Read CM. Rosenfeld MN. J. Chem. Soc., Perkin Trans. 1  1981,  1473 
    CrossrefGoogle Scholar
  • 22 Mackenzie NE. Surendrakumar S. Thomson RH. Cowe HJ. Cox PJ. J. Chem. Soc., Perkin Trans. 1  1986,  2233 
    CrossrefGoogle Scholar
  • 23 Martínez A. Fernández M. Estévez JC. Estévez RJ. Castedo L. Tetrahedron  2005,  61:  485 
    CrossrefGoogle Scholar
  • 24 Cruces J. Estévez JC. Estévez RJ. Castedo L. Heterocycles  2000,  53:  1041 
    CrossrefGoogle Scholar
  • 25 Robineon RK. Moeettig E. J. Am. Chem. Soc.  1939,  61:  1148 
    CrossrefGoogle Scholar
  • 26 Perrin DD. Armarego WLF. Purification of Laboratory Chemicals   Pergamon; Oxford: 1988. 
    Google Scholar
13

http://www.ncbi.nlm.nih.gov/sites/entrez, search PubChem Compound for CID362142.