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Efficient synthesis of functionalized 2,5-dihydrofurans and 1,5-dihydro-2H-pyrrol-2-ones by reaction of isocyanides with activated acetylenes in the presence of hexachloroacetone

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Abstract

Isocyanides react smoothly with dimethyl acetylenedicarboxylate in the presence of hexachloroacetone to produce dimethyl 5-[alkyl(aryl)imino]-2,2-bis(trichloromethyl)-2,5-dihydro-furan-3,4-dicarboxylates in high yields. When the reaction was performed with dibenzoylacetylene, 3-benzoyl-1-alkyl-4-chloro-5-hydroxy-5-phenyl-1,5-dihydro-2H-pyrrol-2-ones were obtained.

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Authors and Affiliations

  1. Chemistry Department, Tarbiat Modares University, Tehran, Iran

    Issa Yavari, Maryam Sabbaghan & Zinatossadat Hossaini

Authors
  1. Issa Yavari
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  2. Maryam Sabbaghan
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  3. Zinatossadat Hossaini
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Correspondence to Issa Yavari.

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Correspondence: Issa Yavari, Chemistry Department, Tarbiat Modares University, Tehran, Iran.

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Yavari, I., Sabbaghan, M. & Hossaini, Z. Efficient synthesis of functionalized 2,5-dihydrofurans and 1,5-dihydro-2H-pyrrol-2-ones by reaction of isocyanides with activated acetylenes in the presence of hexachloroacetone. Monatsh Chem 139, 625–628 (2008). https://doi.org/10.1007/s00706-007-0810-3

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  • DOI: https://doi.org/10.1007/s00706-007-0810-3

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