Download PDF
Synlett 2003(8): 1183-1185
DOI: 10.1055/s-2003-39886
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Improved Synthesis of Substituted Quinoxalines from New N=N-Polymer-bound 1,2-Diaza-1,3-butadienes

Orazio A. Attanasi, Lucia De Crescentini, Paolino Filippone*, Fabio Mantellini*, Stefania Santeusanio
Istituto di Chimica Organica, Università degli Studi di Urbino, Piazza della Repubblica 13, 61029 Urbino, Italy
Fax: +39(0722)2907; e-Mail: filippone@uniurb.it;
Further Information

Publication History

Received 20 March 2003
Publication Date:
11 June 2003 (online)

    Permissions and Reprints All articles of this category

Abstract

The first general protocol for the preparation of different N=N-polymer-bound 1,2-diaza-1,3-butadienes is reported. The utility of these supported reagents in the solid-phase in the preparation of 3-methyl quinoxaline-2-carboxylates by reaction with aromatic 1,2-diamines is presented.

Key words

1,2-diaza-1,3-butadienes - hydrazones - Michael addition - quinoxalines - solid-phase synthesis

    References

  • 1a Attanasi OA. Caglioti L. Org. Prep. Proced. Int.  1986,  18:  299 
    Google Scholar
  • 1b Attanasi OA. Filippone P. Synlett  1997,  1128 
    Google Scholar
  • 1c Attanasi OA. De Crescentini L. Filippone P. Mantellini F. Santeusanio S. Arkivoc  2002,  274 
    Google Scholar
  • 2a Banert K. In Targets in Heterocyclic Systems - Chemistry and Properties   Vol. 3:  Attanasi OA. Spinelli D. Società Chimica Italiana; Rome: 2000.  p.1 
    Google Scholar
  • 2b Polanc S. In Targets in Heterocyclic Systems - Chemistry and Properties   Vol. 3:  Attanasi OA. Spinelli D. Società Chimica Italiana; Rome: 2000.  p.33 ; and references cited therein
    Google Scholar
  • 3a Attanasi OA. De Crescentini L. Filippone P. Foresti E. Mantellini F. J. Org. Chem.  2000,  65:  2820 
    Google Scholar
  • 3b Abbiati G. Arcadi A. Attanasi OA. De Crescentini L. Rossi E. Tetrahedron  2001,  57:  2031 
    Google Scholar
  • 3c Attanasi OA. De Crescentini L. Filippone P. Fringuelli F. Mantellini F. Matteucci M. Piermatti O. Pizzo F. Helv. Chim. Acta  2001,  84:  513 
    Google Scholar
  • 3d Attanasi OA. De Crescentini L. Filippone P. Mantellini F. New J. Chem.  2001,  25:  534 
    Google Scholar
  • 3e Attanasi OA. De Crescentini L. Filippone P. Mantellini F. Synlett  2001,  557 
    Google Scholar
  • 3f Attanasi OA. Filippone P. Guidi B. Mantellini F. Santeusanio S. Synthesis  2001,  1837 
    Google Scholar
  • 3g Rossi E. Arcadi A. Abbiati G. Attanasi OA. De Crescentini L. Angew. Chem. Int. Ed.  2002,  41:  1400 
    Google Scholar
  • 3h Attanasi OA. De Crescentini L. Favi G. Filippone P. Mantellini F. Santeusanio S. Synthesis  2002,  1546 
    Google Scholar
  • 3i Attanasi OA. De Crescentini L. Favi G. Filippone P. Mantellini F. Santeusanio S. J. Org. Chem.  2002,  67:  8178 
    Google Scholar
  • 3j Attanasi OA. De Crescentini L. Favi G. Filippone P. Giorgi G. Mantellini F. Santeusanio S. J. Org. Chem.  2002,  68:  1947 
    Google Scholar
  • 4 Attanasi OA. Filippone P. Guidi B. Hippe T. Mantellini F. Tietze LF. Tetrahedron Lett.  1999,  40:  9277 
    CrossrefGoogle Scholar
  • 5 Attanasi OA. De Crescentini L. Filippone P. Mantellini F. Tietze LF. Tetrahedron  2001,  57:  5855 
    CrossrefGoogle Scholar
  • 6a Emerson DW. Emerson RR. Joshi SC. Sorensen EM. Nrek J. J. Org. Chem.  1979,  44:  4634 
    CrossrefPubMedGoogle Scholar
  • 6b Kamogawa H. Kanzawa A. Kodoja M. Naito T. Nanasawa M. Bull. Chem. Soc. Jpn.  1983,  56:  762 
    CrossrefPubMedGoogle Scholar
  • 6c Galioglu O. Auar A. Eur. Polym. J.  1989,  25:  313 
    CrossrefPubMedGoogle Scholar
  • 6d Hu Y. Baudart S. Porco JA. J. Org. Chem.  1999,  64:  1049 
    CrossrefPubMedGoogle Scholar
  • 7a Sakata G. Makino K. Kurasawa J. Heterocycles  1988,  27:  2481 ; and references cited therein
    CrossrefGoogle Scholar
  • 7b Sato N. Pyrazines and Benzo Derivatives, In Comprehensive Heterocyclic Chemistry   Vol. 6:  Katritzky AR. Rees CW. Scriven EFV. Pergamon Press; New York: 1996. 
    CrossrefGoogle Scholar
  • 7c Progress in Heterocyclic Chemistry   Vol. 1-7:  Suschitzky H. Scriven EFV. Pergamon Press; Oxford: 1989-1995. 
    CrossrefGoogle Scholar
  • 7d Progress in Heterocyclic Chemistry   Vol. 8:  Suschitzky H. Gribble GW. Pergamon Press; Oxford: 1996. 
    CrossrefGoogle Scholar
  • 7e Progress in Heterocyclic Chemistry   Vol. 9-12:  Gribble GW. Gilchrist TL. Pergamon Press; Oxford: 1997-2000. 
    CrossrefGoogle Scholar
  • 8 Attanasi OA. De Crescentini L. Filippone P. Mantellini F. Santeusanio S. Helv. Chim. Acta  2001,  84:  2379 
    Google Scholar
  • 9 Wu Z. Ede NJ. Tetrahedron Lett.  2001,  42:  8115 
    CrossrefGoogle Scholar