Synthesis 2009(13): 2171-2174  
DOI: 10.1055/s-0029-1216858
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Pyrrolo[3,2,1-ij]quinolin-4-one and Pyrrolo[3,2,1-ij]quinolin-6-one

Hamish McNab*, David J. Nelson, Emma J. Rozgowska
School of Chemistry, The University of Edinburgh, West Mains Road, Edinburgh, EH9 3JJ, UK
Fax: +44(131)6504743; e-Mail: H.McNab@ed.ac.uk;
Further Information

Publication History

Received 2 February 2009
Publication Date:
02 June 2009 (online)

Abstract

The parent pyrrolo[3,2,1-ij]quinolin-4-one and pyrrolo[3,2,1-ij]quinolin-6-one ring systems were made by pyrolysis of appropriate acrylates. In the first case, the cyclisation was effected by flash vacuum pyrolysis (FVP) at 950 ˚C, in the second case a cyclisation-dehydrogenation was carried out in one step by FVP over a tungsten trioxide catalyst at 525 ˚C.

    References

  • Pyrrolo[3,2,1-ij]quinolin-4-ones:
  • 1a Tonder JE. Hosseini M. Ahrenst AB. Tanner D. Org. Biomol. Chem.  2004,  2:  1447 
  • 1b Baccichetti F. Marzano C. Carlassare F. Guiotto A. Bordin F. J. Photochem. Photobiol., B  1997,  40:  299 
  • 1c Vedaldi D. Frank S. Pozzan A. Miolo G. Dall"Acqua F. Caffieri S. Rodighiero P. Guiotto A. Farmaco  1994,  49:  615 
  • 1d Rodighiero P. Chilin A. Manzini P. Castellin A. Guiotto A. Bordin F. Carlassare F. Marzano C. Baccichetti F. Farmaco  1994,  49:  607 
  • 1e Black DStC. Bowyer MC. Catalano MM. Ivory AJ. Keller PA. Kumar N. Nugent SJ. Tetrahedron  1994,  50:  10497 
  • 1f Rodighiero P. Chilin A. Bandoli G. Manzini P. Castellin A. Guiotto A. Gazz. Chim. Ital.  1994,  124:  167 
  • 1g Baccichetti F. Carlassare F. Marzano C. Guiotto A. Rodighiero P. Chilin A. Bordin F. J. Photochem. Photobiol., B  1994,  24:  101 
  • 1h Jones SG. Young AR. Truscott TG. J. Photochem. Photobiol., B  1993,  23:  223 
  • 1i Chilin A. Rodighiero P. Pastorini G. Guiotto A. J. Org. Chem.  1991,  56:  980 
  • 1j Black DStC. Ivory AJ. Keller PA. Kumar N. Synthesis  1989,  322 
  • 1k Franke U. Roeder E. Arch. Pharm. (Weinheim, Ger.)  1976,  309:  185 
  • 1l Ziegler E. Junek H. Noelken E. Gelfert K. Salvador R. Monatsh. Chem.  1961,  92:  814 
  • Pyrrolo[3,2,1-ij]quinolin-6-ones:
  • 2a Dorow RL. Herrinton PM. Hohler RA. Maloney MT. Mauragis MA. McGhee WE. Moeslein JA. Strohbach JW. Veley MF. Org. Process Res. Dev.  2006,  10:  493 
  • 2b Black DStC. Kumar N. Mitchell PSR. J. Org. Chem.  2002,  67:  2464 
  • 2c Abe N. Fujii H. Kakehi A. Heterocycles  2001,  55:  1189 
  • 2d Blurton P. Brickwood A. Dhanak D. Heterocycles  1997,  45:  2395 
  • 2e Neidlein R. Rietdorf U. Arch. Pharm. (Weinheim, Ger.)  1982,  315:  897 
  • 2f Neidlein R. Rietdorf U. Arch. Pharm. (Weinheim, Ger.)  1982,  315:  901 
  • 2g Neidlein R. Rietdorf U. Monatsh. Chem.  1982,  113:  623 
  • 2h Neidlein R. Heid H. Arch. Pharm. (Weinheim, Ger.)  1979,  312:  801 
  • 2i Gatta F. Tomassetti M. Zaccari V. Landi Vittory R. Eur. J. Med. Chem.  1974,  9:  133 
  • 3 For a review, see: Gaber AM. McNab H. Synthesis  2001,  2059 
  • 4 For related uses of FVP/WO3, see: Campbell JA. McDougald G. McNab H. Rees LVC. Tyas RG. Synthesis  2007,  3179 
  • 5 Cross PE. Dickenson RP. Parry MJ. Randall MJ. J. Med. Chem.  1986,  29:  342 
  • 6 McNab H. Tyas RG. J. Org. Chem.  2007,  72:  8760 
  • 7 For a review, see: Jones G. In Quinolines   Vol. 1:  Jones G. Wiley; New York: 1977. 
  • 8a Campbell SE. Comer MC. Derbyshire PA. Despinoy XLM. McNab H. Morrison R. Sommerville CC. Thornley C. J. Chem. Soc., Perkin Trans. 1  1997,  2195 
  • 8b McNab H. Thornley C. J. Chem. Soc., Perkin Trans. 1  1997,  2203 
  • 10 Somei M. Saida Y. Komura N. Chem. Pharm. Bull. Jpn.  1986,  34:  4116 
  • 11 The corresponding ethyl ester is known, see: Rapoport H. Windgassen RJ. Hughes NA. Onak TP. J. Am. Chem. Soc.  1960,  82:  4404 
9

McNab, H.; O’Neill, W. J.; Rozgowska, E. J. unpublished work.