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1-Oxa-3-azapentalen-2-ones as Precursors of cis-2-Amino Alcohols: Synthesis from Propargyl Alcohols, CO2, and Amines Using an Intramolecular Amidoalkylation Reaction of Oxazolidin-2-ones

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Abstract

The reaction of 5-methyl-5-(4-methyl-3-pentenyl)-4-methylene-1,3-dioxolan-2-one with primary amines gives the corresponding 4-hydroxy-4-methyloxazolidin-2-ones. These undergo an intramolecular amidoalkylation reaction to form 1-oxa-3-azapentalen-2-ones which are potential precursors of cyclopentanyl cis-2-amino alcohols.

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Authors and Affiliations

  1. Russian Academy of Sciences, N. D. Zelinsky Institute of Organic Chemistry, Moscow, 117913

    N. B. Chernysheva, A. A. Bogolyubov & V. V. Semenov

  2. Russian Academy of Sciences, A. N. Nesmeyanov Institute of Organoelemental Compounds, Moscow, 117813

    V. V. Nesterov & M. Yu. Antipin

Authors
  1. N. B. Chernysheva
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  2. A. A. Bogolyubov
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  3. V. V. Nesterov
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  4. M. Yu. Antipin
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  5. V. V. Semenov
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Chernysheva, N.B., Bogolyubov, A.A., Nesterov, V.V. et al. 1-Oxa-3-azapentalen-2-ones as Precursors of cis-2-Amino Alcohols: Synthesis from Propargyl Alcohols, CO2, and Amines Using an Intramolecular Amidoalkylation Reaction of Oxazolidin-2-ones. Chemistry of Heterocyclic Compounds 39, 925–936 (2003). https://doi.org/10.1023/A:1026154623110

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  • DOI: https://doi.org/10.1023/A:1026154623110

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