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Reaction between alkyl isocyanides and isopropylidene Meldrum’s acid in the presence of bidentate nucleophiles

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Summary

The reaction between alkyl isocyanides and isopropylidene Meldrum’s acid in the presence of 1,2-ethanediol leads to N 1-(alkyl)-2-(5,7-dioxo-1,4-dioxepane-6-yl)-2-methylpropanamides. 1,3-Propanediol or 1,4-butanediol produce hydroxyalkyl 1-(tert-butyl)-4,4-dimethyl-2,5-dioxo-3-pyrrolidinecarboxylates. When the reaction was performed in the presence of catechol, bis(2-hydroxyphenyl) 2-[2-(tert-butylamino)-1,1-dimethyl-2-oxoethyl]malonate was obtained. 2-Aminophenols react with alkyl isocyanides in the presence of isopropylidene Meldrum’s acid to produce 1-alkyl-N 3-(2-hydroxyaryl)-4,4-dimethyl-2,5-dioxo-3-pyrrolidinecarboxamides in good yields.

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Authors and Affiliations

  1. Department of Chemistry, Tarbiat Modarres University, PO Box 14115-175, Tehran, Iran

    Issa Yavari, Maryam Sabbaghan & Zinatossadat Hossaini

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  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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Yavari, I., Sabbaghan, M. & Hossaini, Z. Reaction between alkyl isocyanides and isopropylidene Meldrum’s acid in the presence of bidentate nucleophiles. Mol Divers 11, 1–5 (2007). https://doi.org/10.1007/s11030-006-9052-2

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  • DOI: https://doi.org/10.1007/s11030-006-9052-2

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