Download PDF
Synthesis 2003(16): 2518-2524  
DOI: 10.1055/s-2003-42411
PAPER
© Georg Thieme Verlag Stuttgart · New York

A General Procedure for the Synthesis of Pyrido-Condensed Heterocycles

Donato Donati, Serena Ferrini, Stefania Fusi, Fabio Ponticelli*
Department of Chemistry, University of Siena, via A. Moro, 53100 Siena, Italy
Fax: +39(577)234278; e-Mail: ponticelli@unisi.it;
Further Information

Publication History

Received 2 July 2003
Publication Date:
29 September 2003 (online)

    Permissions and Reprints All articles of this category

Abstract

Reaction of 4-substituted isoxazolo[4,5-c]- and [5,4-b]pyridines with Mo(CO)6 in refluxing methanol is an efficient and versatile procedure for the preparation of functionalized pyrido-condensed heterocycles containing from five to eight atoms in the ring.

Key words

condensed pyridines - molybdenum hexacarbonyl - ring opening - rearrangements - benzodiazocines

    References

  • 1a Maemoto T. Finlayson K. Olverman HJ. Akahane A. Horton RW. Butcher SP. Br. J. Pharmacol.  1997,  122:  1202 
    CrossrefGoogle Scholar
  • 1b Lunt E. Newton CG. In Comprehensive Heterocyclic Chemistry   Vol. 3:  Katritzki AR. Rees CW. Boulton AJ. McKillop A. Pergamon; Oxford: 1984.  p.199 
    CrossrefGoogle Scholar
  • 1c Radinov R. Hainova M. Simova E. Tyutyulkova N. Gorantcheva J. Arch. Pharm. (Weinheim, Ger.)  1987,  320:  704 
    CrossrefGoogle Scholar
  • 1d inventors; Deutsche Gold und Silber-Scheideanstsalt vorm. Roessler, French Patent  2162482.  ; Chem. Abstr. 1974, 80, 3561
    Crossref
  • 1e Carboni S. Da Settimo A. Bertini D. Ferrarini PL. Livi O. Tonetti I. Farmaco Ed. Sci.  1975,  237 
    CrossrefGoogle Scholar
  • 1f Carboni S. Da Settimo A. Bertini D. Ferrarini PL. Livi O. Tonetti I. Farmaco Ed. Sci.  1976,  322 
    CrossrefGoogle Scholar
  • 1g Walser A. Fryer RI. In The Chemistry of Heterocyclic Compounds   Vol. 50:  Fryer RI. Wiley; New York: 1991.  p.947-1052  
    CrossrefGoogle Scholar
  • 1h Ho W. Kukla MJ. Breshin HJ. Ludovici DW. Grous PP. Diamond CJ. Miranda M. Rodgers JD. Ho CJ. De Clerq E. Pauwels R. Andries K. Janssen MAC. Janssen PAJ. J. Med. Chem.  1995,  38:  794 
    CrossrefGoogle Scholar
  • 2a Dorgan RJ. Parrick J. Hardy CR. J. Chem. Soc., Perkin Trans. 1  1980,  938 
    CrossrefGoogle Scholar
  • 2b Thompson MD. J. Heterocycl. Chem.  1986,  23:  1545 
    CrossrefGoogle Scholar
  • 2c John R. Seitz G. Chem. Ber.  1990,  123:  133 
    CrossrefGoogle Scholar
  • 3a Donati D. Fusi S. Ponticelli F. Tetrahedron Lett.  2002,  43:  9527 
    CrossrefGoogle Scholar
  • 3b Giorgi GL. Ponticelli F. Czira G. Vékèy K. J. Am. Soc. Mass Spectrom.  1995,  6:  962 
    CrossrefGoogle Scholar
  • 3c Donati D. Fusi S. Ponticelli F. Eur. J. Org. Chem.  2002,  4211 
    CrossrefGoogle Scholar
  • 4a Adembri G. Ponticelli F. Tedeschi P. J. Chem. Soc., Perkin Trans. 1  1975,  2190 
    CrossrefGoogle Scholar
  • 4b Adembri G. Camparini A. Ponticelli F. Tedeschi P. J. Heterocycl. Chem.  1979,  16:  49 
    CrossrefGoogle Scholar
  • 4c Camparini A. Ponticelli F. Tedeschi P. J. Heterocycl. Chem.  1977,  14:  435 
    CrossrefGoogle Scholar
  • 4d Adembri G. Camparini A. Ponticelli F. Tedeschi P. Tetrahedron Lett.  1982,  23:  4375 
    CrossrefGoogle Scholar
  • 5 Denzel T. Hohn H. Arch. Pharm. (Weinheim, Ger.)  1973,  306:  746 
    CrossrefGoogle Scholar
  • 6 Nitta M. Kobayashi T. J. Chem. Soc., Perkin Trans. 1  1985,  1401 
    CrossrefGoogle Scholar
  • 7 Donati D. Fusi S. Ponticelli F. Heterocycles  1988,  27:  1899 
    CrossrefGoogle Scholar
  • 8a Sheldrick GM. SHELXL-97. Program for the Refinement of Crystal Structure   University of Gottingen; Germany: 1997. 
    Google Scholar
  • 8b

    Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-204629. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: (internat.) +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk]