PDF icon PDF herunterladen
Synthesis 2011(4): 563-570  
DOI: 10.1055/s-0030-1258417
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile Multicomponent Synthesis of Novel 2,3-Dihydropyran Derivatives under Solvent-Free Conditions

Li Li, Qi Wu*, Bo-Kai Liu, Xian-Fu Lin*
Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China
Fax: +86(571)87952618; e-Mail: llc123@zju.edu.cn;
Weitere Informationen

Publikationsverlauf

Received 10 November 2010
Publikationsdatum:
21. Januar 2011 (online)

   Lizenzen und Reprints Alle Artikel dieser Rubrik
Preview

Abstract

A series of new, substituted 2,3-dihydropyran derivatives were synthesized by one-pot, three-component reactions of aldehydes, 1,3-dicarbonyl derivatives, and vinyl ethers catalyzed by ethylenediamine diacetate (EDDA) under solvent-free conditions. This new, simple, and efficient, solvent-free, one-pot approach to the substituted 2,3-dihydropyran scaffold starting from simple substrates was found to take place directly.

Key words

multicomponent reaction - one-pot - 2,3-dihydropyran - solvent-free - EDDA

    References

  • 1a Bannwarth W. Felder E. Combinatorial Chemistry   Wiley-VCH; Weinheim: 2000. 
  • 1b Zhu J. Bienaymé H. Multicomponent Reactions   Wiley-VCH; Weinheim: 2005. 
  • 1c Döling A. Chem. Rev.  2006,  106:  17 
    Suche in Google Scholar
  • 1d Ganem B. Acc. Chem. Res.  2009,  42:  463 
    Suche in Google Scholar
  • 1e Toure BB. Hall DG. Chem. Rev.  2009,  109:  4439 
    Suche in Google Scholar
  • 1f D’Souza DM. Muller TJJ. Chem. Soc. Rev.  2007,  36:  1095 
    Suche in Google Scholar
  • 2a Walsh PJ. Li H. Parrodi CA. Chem. Rev.  2007,  107:  2503 
    Suche in Google Scholar
  • 2b Hobbs HR. Thomas NR. Chem. Rev.  2007,  107:  2786 
    Suche in Google Scholar
  • 2c Martins MAP. Frizzo CP. Moreira DN. Buriol L. Machado P. Chem. Rev.  2009,  109:  4140 
    Suche in Google Scholar
  • 3a Ciufolini MA. Byrne NE. J. Chem. Soc., Chem. Commun.  1988,  1230 
  • 3b Ciufolini MA. Bishop MJ.
    J. Chem. Soc., Chem. Commun.  1993,  1463 
  • 3c Bennabi S. Narkunan K. Rousset L. Bouchu D. Ciufolini MA. Tetrahedron Lett.  2000,  41:  8873 
    Suche in Google Scholar
  • 4a Ichihara A. Oikawa H. Curr. Org. Chem.  1998,  2:  365 
    Suche in Google Scholar
  • 4b Tietze LF. Böhnke N. Dietz S. Org. Lett.  2009,  11:  2948 
    Suche in Google Scholar
  • 4c Hayman CM. Larsen DS. Simpson J. Bailey KB. Gill GS. Org. Biomol. Chem.  2006,  4:  2794 
    Suche in Google Scholar
  • 4d Audrain H. Thorauge J. Hazell RG. Jørgensen KA. J. Org. Chem.  2000,  65:  4487 
    Suche in Google Scholar
  • 4e Tietze LF. Montenbruck A. Schneider C. Synlett  1994,  509 
  • 4f Tietze LF. Schneider C. Montenbruck A. Angew. Chem., Int. Ed. Engl.  1994,  33:  980 
    Suche in Google Scholar
  • 4g Tietze LF. Hartfiel U. Hübsch T. Voss E. Bogdanowiczszwed K. Wichmann J. Liebigs Ann. Chem.  1991,  275 
  • 4h De Gaudenzi L. Apparao S. Schmidt RR. Tetrahedron  1990,  46:  277 
    Suche in Google Scholar
  • 5a Al-Badri H. Collignon N. Maddaluno J. Masson S. Chem. Commun.  2000,  1191 
  • 5b Al-Badri H. Maddaluno J. Masson S. Collignon N. J. Chem. Soc., Perkin Trans. 1  1999,  2255 
  • 6 Cordaro JG. McCusker JK. Bergman RG. Chem. Commun.  2002,  1496 
  • 7 Dujardin G. Leconte S. Coutable L. Brown E. Tetrahedron Lett.  2001,  42:  8849 
    CrossrefSuche in Google Scholar
  • 8 Wada E. Pei W. Yasuoka H. Chin U. Kanemasa S. Tetrahedron  1996,  52:  1205 
    CrossrefSuche in Google Scholar
  • 9a Tietze LF. Chem. Rev.  1996,  96:  115 
    Suche in Google Scholar
  • 9b Tietze LF. Modi A. Med. Res. Rev.  2000,  20:  304 
    Suche in Google Scholar
  • 9c Tietze LF. Zhou Y. Angew. Chem. Int. Ed.  1999,  38:  2045 
    Suche in Google Scholar
  • 9d Tietze LF. Evers H. Töpken E. Angew. Chem. Int. Ed.  2001,  40:  903 
    Suche in Google Scholar
  • 9e Tietze LF. Evers H. Töpken E. Helv. Chim. Acta  2002,  85:  4200 
    Suche in Google Scholar
  • 9f Tietze LF. Bachmann J. Wichmann J. Burkhardt O. Synthesis  1994,  1185 
  • 10 Tietze LF. Hippe T. Steinmetz A. Synlett  1996,  1043 
    Thieme Connect
  • 11 Radi M. Bernardo V. Bechi B. Castagnolo D. Pagano M. Botta M. Tetrahedron Lett.  2009,  50:  6572 
    CrossrefSuche in Google Scholar