Download PDF
Synthesis 2012; 44(11): 1686-1692
DOI: 10.1055/s-0031-1289761
paper
© Georg Thieme Verlag Stuttgart · New York

Convenient MCRs Synthesis of Trifluoromethylated Pyrano[4,3-b]pyrans and Their Further Transformation

Wei Wang
a   Department of Chemistry, School of Science, Shanghai University, No. 99, Shangda Road, Shanghai 200444, P. R. of China, Fax: +86(21)66134594   Email: lpsong@shu.edu.cn
,
Jia Li
a   Department of Chemistry, School of Science, Shanghai University, No. 99, Shangda Road, Shanghai 200444, P. R. of China, Fax: +86(21)66134594   Email: lpsong@shu.edu.cn
,
Li Zhang
a   Department of Chemistry, School of Science, Shanghai University, No. 99, Shangda Road, Shanghai 200444, P. R. of China, Fax: +86(21)66134594   Email: lpsong@shu.edu.cn
,
Liping Song*
a   Department of Chemistry, School of Science, Shanghai University, No. 99, Shangda Road, Shanghai 200444, P. R. of China, Fax: +86(21)66134594   Email: lpsong@shu.edu.cn
b   Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. of China
,
Min Zhang
a   Department of Chemistry, School of Science, Shanghai University, No. 99, Shangda Road, Shanghai 200444, P. R. of China, Fax: +86(21)66134594   Email: lpsong@shu.edu.cn
,
Weiguo Cao
a   Department of Chemistry, School of Science, Shanghai University, No. 99, Shangda Road, Shanghai 200444, P. R. of China, Fax: +86(21)66134594   Email: lpsong@shu.edu.cn
,
Hongmei Deng
c   Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, P. R. of China
,
Min Shao
c   Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 20 March 2012

Accepted after revision: 11 April 2012

Publication Date:
08 May 2012 (online)

    Permissions and Reprints All articles of this category


Abstract

Ethyl 2-hydroxy-7-methyl-5-oxo-4-aryl-2-(trifluoromethyl)-3,4-dihydro-2H,5H-pyrano[4,3-b]pyran-3-carboxylate derivatives were synthesized via a one-pot three-component reaction (MCR) promoted by ammonium acetate. The effect of ammonium acetate and the solvent on the reaction efficiency was investigated. Furthermore, treatment of the resultant products with thionyl chloride/pyridine in chloroform gave the corresponding dehydrated products ethyl 4-aryl-7-methyl-5-oxo-2-(trifluoromethyl)-4H,5H-pyrano[4,3-b]pyran-3-carboxylates and the unexpected defluorinated products ethyl 3-aryl-6-methyl-4-oxo-4H-furo[3,2-c]pyran-2-carboxylates. The novel products are highly important for the synthesis of related fluorinated fused heterocyclic compounds.

Key words

MCR - fluorinated heterocycle - ethyl trifluoroacetoacetate - dehydration

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
  • Supporting Information
 

  • References

  • 1 Filler R, Banks RE. Organofluorine Chemicals and Their Industrial Applications. Ellis Horwood; Chichester: 1979
    Google Scholar
    • 2a Welch JT. Tetrahedron 1987; 43: 3123
      Crossref
    • 2b Frezza M, Balestrino D, Soulère L, Reverchon S, Queneau Y, Forestier C, Doutheau A. Eur. J. Org. Chem. 2006; 4731
    • 2c Leroux F, Lefebvre O, Schlosser M. Eur. J. Org. Chem. 2006; 3147
    • 2d Buscemi S, Pace A, Piccionello A, Macaluso G, Vivona N. J. Org. Chem. 2005; 70: 3288
      Crossref
    • 4a Welch JT. Fluorine in Bioorganic Chemistry. Eswarakrishnan S. Wiley; New York: 1991
      CrossrefGoogle Scholar
    • 4b Prabhakaran J, Underwood MD, Parsey RV, Arango V, Majo VJ, Simpson NR, Heertum RV, Mann JJ, Kumar JS. D. Bioorg. Med. Chem. 2007; 15: 1802
      Crossref
    • 5a Filler R, Kobayashi Y. Biomedicinal Aspects of Fluorine Chemistry. Kodansha & Elsevier Biomedical; Tokyo: 1982
      Google Scholar
    • 5b Filler R, Kobayashi Y, Yagupolskii LM. Organofluorine Compounds in Medical Chemistry and Biomedical Application. Elsevier; Amsterdam: 1993
      Google Scholar
    • 6a Domling A, Ugi I. Angew. Chem. Int. Ed. 2000; 39: 3168
      CrossrefPubMed
    • 6b Suresh Babu AR, Raghunathan R. Tetrahedron Lett. 2006; 47: 9221
      Crossref
    • 7a Yi H, Song LP, Wang W, Liu JN, Zhu SZ, Deng HM, Shao M. Chem. Commun. 2010; 46: 6941
      Crossref
    • 7b Wang PY, Song LP, Yi H, Zhang M, Deng HM, Shao M. Tetrahedron Lett. 2010; 51: 3975
      Crossref
    • 7c Song LP, Li XF, Xing CH, Li DM, Zhu SZ, Deng HM, Shao M. Synlett 2010; 830
      Article in Thieme Connect
    • 7d Dai BF, Song LP, Wang PY, Yi H, Jin GF, Zhu SZ, Shao M. Synlett 2009; 1842
      Article in Thieme Connect
    • 7e Song SD, Song LP, Dai BF, Yi H, Jin GF, Zhu SZ, Shao M. Tetrahedron 2008; 64: 5728
      Crossref
    • 7f Li DM, Song LP, Li XF, Xing CH, Peng WM, Zhu SZ. Eur. J. Org. Chem. 2007; 3520
    • 7g Li DM, Song LP, Song SD, Zhu SZ. J. Fluorine Chem. 2007; 128: 952
      Crossref
    • 7h Li XF, Song LP, Xing CH, Zhao JW, Zhu SZ. Tetrahedron 2006; 62: 2255
      Crossref
  • 8 Atkinson RS, Barker E, Edwards PJ, Thomson GA. J. Chem. Soc., Perkin Trans. 1 1995; 1533
    • 9a Katsuyama I, Ogawa S, Yamaguchi Y, Funabiki K, Matsui M, Muramatsu H, Shibata K. Synthesis 1997; 1321
      Article in Thieme Connect
    • 9b Amii H, Obayashi KT, Terasawa H, Uneyama K. Org. Lett. 2001; 3: 3103
      Crossref
    • 9c Xing CH, Zhu SZ. J. Org. Chem. 2004; 69: 6486
      Crossref
  • 10 Rahul RN, Vijay VK, Sachin SB, Devanand BS. Eur. J. Med. Chem. 2005; 40: 1325
    Crossref
  • 11 Hansen AL, Skrydstrup T. Org. Lett. 2005; 7: 5585
    Crossref
  • 12 Gao Y, Tu SJ, Shi F, Wang Q, Zhu XT, Shi DQ. Synth. Commun. 2007; 37: 1603
    Crossref
    • 13a de March P, Moreno-Mañas M, Casado J, Pleixats R, Roca JL, Trius A. J. Heterocycl. Chem. 1984; 21: 85
      Crossref
    • 13b de March P, Moreno-Mañas M, Casado J, Pleixats R, Roca JL, Trius A. J. Heterocycl. Chem. 1984; 21: 1369
      Crossref
  • 14 Sagar R, Park JM, Koh M, Park SB. J. Org. Chem. 2009; 74: 2171
    Crossref
  • 15 CCDC-860235 (4c) and CCDC-860236 (6a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif
  • 16 Zhu SZ, Song LP, Jin GF, Dai BF, Hao J. Curr. Org. Chem. 2009; 13: 1015
    Crossref
    • 17a Cadierno V, Díez J, Gimeno J, Nebra N. J. Org. Chem. 2008; 73: 5852
      Crossref
    • 17b Conreaux D, Belot S, Desbordes P, Monteiro N, Balme G. J. Org. Chem. 2008; 73: 8619 ; and references cited therein
      Crossref