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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

Authors

  • 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
Further Information

Publication History

Received: 20 March 2012

Accepted after revision: 11 April 2012

Publication Date:
08 May 2012 (online)

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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

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