Dimethoxyethane as an Alternative Solvent for Schimdt Reactions. Preparation of Homoquiral N-(5-Oxazolyl) oxazolidinones from N-Acetoacetyl Derivatives of Oxazolidinones

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

doi:10.1016/0040-4020(95)00989-2

Dimethoxyethane as an Alternative Solvent for Schimdt Reactions. Preparation of Homoquiral N-(5-Oxazolyl) oxazolidinones from N-Acetoacetyl Derivatives of Oxazolidinones

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

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

35 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 language	English
Pages (from-to)	1609-1616
Journal	Tetrahedron
Volume	52
Issue number	5
DOIs	https://doi.org/10.1016/0040-4020(95)00989-2
Publication status	Published - 29 Jan 1996

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title = "Dimethoxyethane as an Alternative Solvent for Schimdt Reactions. Preparation of Homoquiral N-(5-Oxazolyl) oxazolidinones from N-Acetoacetyl Derivatives of Oxazolidinones",

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.",

author = "Nicanor G{\'a}lvez and Marcial Moreno-Ma{\~n}as and Sebasti{\'a}n, {Rosa M.} and Adelina Vallribera",

year = "1996",

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doi = "10.1016/0040-4020(95)00989-2",

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Dimethoxyethane as an Alternative Solvent for Schimdt Reactions. Preparation of Homoquiral N-(5-Oxazolyl) oxazolidinones from N-Acetoacetyl Derivatives of Oxazolidinones. / Gálvez, Nicanor; Moreno-Mañas, Marcial; Sebastián, Rosa M. et al.
In: Tetrahedron, Vol. 52, No. 5, 29.01.1996, p. 1609-1616.

Research output: Contribution to journal › Article › Research › peer-review

TY - JOUR

T1 - Dimethoxyethane as an Alternative Solvent for Schimdt Reactions. Preparation of Homoquiral N-(5-Oxazolyl) oxazolidinones from N-Acetoacetyl Derivatives of Oxazolidinones

AU - Gálvez, Nicanor

AU - Moreno-Mañas, Marcial

AU - Sebastián, Rosa M.

AU - Vallribera, Adelina

PY - 1996/1/29

Y1 - 1996/1/29

N2 - 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.

AB - 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.

U2 - 10.1016/0040-4020(95)00989-2

DO - 10.1016/0040-4020(95)00989-2

M3 - Article

SN - 0040-4020

VL - 52

SP - 1609

EP - 1616

JO - Tetrahedron

JF - Tetrahedron

IS - 5

ER -

Dimethoxyethane as an Alternative Solvent for Schimdt Reactions. Preparation of Homoquiral N-(5-Oxazolyl) oxazolidinones from N-Acetoacetyl Derivatives of Oxazolidinones

Abstract

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