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Reactions of Heterocumulenes with Organometallic Reagents: VII. Reactions of Carbanions Derived from Alkoxy- and Alkylthioethenes with Isocyanates as a Simple Route to N-Substituted 2-Alkoxy- and 2-(Alkylthio)acrylamides

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Abstract

Metalated alkoxy- and alkylthioethenes readily add to isocyanates, and subsequent hydrolysis or alkylation of the adducts gives N-mono- and N,N-disubstituted 2-alkoxy- and 2-(alkylthio)acrylamides in up to 86% yield. The reactions with propyl and phenyl isocyanates do not stop at the stage of addition of one isocyanate molecule, and further addition leads to formation of linear and cyclic polyamide structures.

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    N. A. Nedolya, N. I. Shlyakhtina, I. A. Ushakov & A. I. Albanov

  2. Utrecht University, Utrecht, The Netherlands

    L. Brandsma

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  1. N. A. Nedolya
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  2. L. Brandsma
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  3. N. I. Shlyakhtina
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  4. I. A. Ushakov
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  5. A. I. Albanov
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Nedolya, N.A., Brandsma, L., Shlyakhtina, N.I. et al. Reactions of Heterocumulenes with Organometallic Reagents: VII. Reactions of Carbanions Derived from Alkoxy- and Alkylthioethenes with Isocyanates as a Simple Route to N-Substituted 2-Alkoxy- and 2-(Alkylthio)acrylamides. Russian Journal of Organic Chemistry 39, 630–641 (2003). https://doi.org/10.1023/A:1026092725563

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