Synthesis of extended oxazoles II: reaction manifold of 2-(halomethyl)-4,5-diaryloxazoles

[Display omitted] 2-(Halomethyl)-4,5-diphenyloxazoles are effective, reactive scaffolds which can be utilized for synthetic elaboration at the 2-position. Through substitution reactions, the chloromethyl analogue is used to prepare a number of 2-alkylamino-, 2-alkylthio-, and 2-alkoxy-(methyl) oxazo...

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Bibliographic Details
Published in:Tetrahedron letters 2016-02, Vol.57 (7), p.757-759
Main Authors: Patil, Pravin C., Luzzio, Frederick A.
Format: Article
Language:English
Subjects:
Click chemistry
Heterocycles
Ligands
Oxaprozin
Oxazoles
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Summary:[Display omitted] 2-(Halomethyl)-4,5-diphenyloxazoles are effective, reactive scaffolds which can be utilized for synthetic elaboration at the 2-position. Through substitution reactions, the chloromethyl analogue is used to prepare a number of 2-alkylamino-, 2-alkylthio-, and 2-alkoxy-(methyl) oxazoles. The 2-bromomethyl analogue offers a more reactive alternative to the chloromethyl compounds and is useful in the C-alkylation of a stabilized (malonate) carbanion as exemplified by a concise synthesis of Oxaprozin.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2016.01.016