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Domino Michael–O-alkylation: one-pot synthesis of dialkyl 4-oxo-2,3-dihydro-2,3-furandicarboxylates

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Abstract

The KSCN-catalyzed reaction of dialkyl acetylenedicarboxylates with pentane-2,4-dione in acetone, led to dialkyl 2-(1-acetyl-2-oxopropyl)-2-butenedioates in excellent yields. When these reactions were carried out in MEK (butane-2-one), dialkyl 4-oxo-2,3-dihydro-2,3-furandicarboxylates were obtained exclusively. This difference in reactivity is discussed in terms of the possibility of cationic exchange in butane-2-one.

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Authors and Affiliations

  1. Chemistry Department, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran

    Issa Yavari, Mehdi Sirouspour & Sanaz Souri

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  1. Issa Yavari
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  2. Mehdi Sirouspour
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  3. Sanaz Souri
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Correspondence to Issa Yavari.

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Yavari, I., Sirouspour, M. & Souri, S. Domino Michael–O-alkylation: one-pot synthesis of dialkyl 4-oxo-2,3-dihydro-2,3-furandicarboxylates. Mol Divers 15, 451–456 (2011). https://doi.org/10.1007/s11030-010-9265-2

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  • DOI: https://doi.org/10.1007/s11030-010-9265-2

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