Dimethoxyethane as an alternative solvent for Schmidt reactions. Preparation of homochiral N-(5-oxazolyl)oxazolidinones from N-acetoacetyl derivatives of oxazolidinones

Nicanor Gálvez, Marcial Moreno-Mañas, Rosa M. Sebastián, Adelina Vallribera

Research output: Contribution to journalArticleResearchpeer-review

31 Citations (Scopus)

Abstract

Dimethoxyethane is an useful solvent for the Schmidt reaction of ketones and β-ketoesters with sodium azide and methanesulfonic acid to afford amides and amidoesters. This solvent is an alternative to the unsafe chlorinated solvents normally used. A β-diketone and several (4S)-N-(2-alkylacetoacetyl)-4-benzyloxazolidin-2-ones afford oxazoles under those conditions.
Original languageEnglish
Pages (from-to)1609-1616
JournalTetrahedron
Volume52
Issue number5
DOIs
Publication statusPublished - 29 Jan 1996

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