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An improved synthesis of 1,2,4-oxadiazoles on solid support

K D Rice, J M Nuss
Bioorganic & Medicinal Chemistry Letters 2001 March 26, 11 (6): 753-5
The use of tetra-N-butylammonium fluoride (TBAF) as a mild and efficient reagent for the cyclodehydration of O-acyl amidoximes has been extended to the synthesis of 1,2,4-oxadiazoles on solid support. Argopore MB-CHO resin (Argonaut Technologies) was reductively aminated and subsequently acylated with 4-cyanobenzoyl chloride. Conversion of the nitrile to the amidoxime and acylation with a range of acid chlorides in parallel followed by treatment with TBAF under ambient conditions afforded a library of 3,5-disubstituted 1,2,4-oxadiazoles.


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