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Published on: January 3, 2018
Three-component synthesis of highly functionalized 5-acetyloxazoles
Tilman Lechel1, Dieter Lentz, Hans-Ulrich Reissig
1Institut für Chemie und Biochemie, Freie Universität Berlin, Takustrasse 3, 14195 Berlin, Germany.
A flexible three-component synthesis enables easy access to alkoxy-substituted enamides. These intermediates can be converted into 5-acetyloxazoles, useful for further synthetic modifications.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Alkoxy-substituted enamides are valuable synthetic intermediates.
- Efficient methods for their preparation are crucial in organic synthesis.
Purpose of the Study:
- To develop a flexible three-component synthesis for alkoxy-substituted enamides.
- To explore the transformation of these enamides into 5-acetyloxazoles.
Main Methods:
- A three-component reaction involving lithiated alkoxyallenes, nitriles, and carboxylic acids.
- Treatment of the resulting enamides with trifluoroacetic acid.
Main Results:
- Alkoxy-substituted enamides were synthesized efficiently.
- The enamide intermediates were converted to 5-acetyloxazoles in moderate to good yields.
- The 5-acetyl group provides a handle for further synthetic transformations.
Conclusions:
- A versatile and flexible synthetic route to 5-acetyloxazoles has been established.
- The method allows for diverse substituents at the C-2 and C-5 positions.
- This approach offers a valuable tool for constructing complex organic molecules.
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