Tuned methods for conjugate addition to a vinyl oxadiazole; synthesis of pharmaceutically important motifs

The addition of various nucleophiles to a vinyl 1,2,4-oxadiazole is described. Following optimisation, individual protocols tuned for the use of each specific class of reagent have been developed to allow the installation of nitrogen, sulfur, oxygen, and carbon nucleophiles, and leading to the prepa...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2010-06, Vol.8 (12), p.2777-2783
Main Authors: Burns, Alan R, Kerr, Jennifer H, Kerr, William J, Passmore, Joanna, Paterson, Laura C, Watson, Allan J B
Format: Article
Language:English
Subjects:
Carbon - chemistry
Nitrogen - chemistry
Oxadiazoles - chemical synthesis
Oxadiazoles - chemistry
Oxygen - chemistry
Sulfur - chemistry
Vinyl Compounds - chemical synthesis
Vinyl Compounds - chemistry
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Summary:The addition of various nucleophiles to a vinyl 1,2,4-oxadiazole is described. Following optimisation, individual protocols tuned for the use of each specific class of reagent have been developed to allow the installation of nitrogen, sulfur, oxygen, and carbon nucleophiles, and leading to the preparation of a series of compounds containing the pharmaceutically important oxadiazole motif.
ISSN:1477-0520
1477-0539
DOI:10.1039/c001772h