1-OXA-3-AZAPENTALEN-2-ONES AS PRECURSORS OF <i>ci</i>s-2-AMINO ALCOHOLS: SYNTHESIS FROM PROPARGYL ALCOHOLS, CO<sub>2</sub>, AND AMINES USING AN INTRAMOLECULAR AMIDOALKYLATION REACTION OF OXAZOLIDIN-2-ONES

Authors

  • Н. Б. Чернышева N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991
  • А. А. Боголюбов N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991
  • В. В. Нестеров A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow 119991
  • М. Ю. Антипин A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow 119991
  • В. В. Семенов N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991

Keywords:

2-amino alcohols, 4-hydroxyoxazolidin-2-ones, 4-methylene-1,3-dioxolan-2-ones, 1-oxa-3-azapentalen-2-ones, intramolecular amidoalkylation, X-ray structural analysis, stereoselectivity

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.

How to Cite
N. B. Chernysheva, N. B.; Bogolyubov, A. A.; Nesterov, V. V.; Antipin, M. Yu.; Semenov, V. V. Chem. Heterocycl. Compd. 2003, 39, 925. [Khim. Geterotsikl. Soedin. 2003, 1067.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1026154623110

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Published

2003-07-25

Issue

No. 7 (2003)

Section

Original Papers