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13.6.1.1.3.3 Method 3: From an Amidoxime and a Nitrile Derivative

DOI: 10.1055/sos-SD-013-00175

Hemming, K.Science of Synthesis, (200413143.

This is a popular and versatile method that allows the nitrile carbon to function as the single-carbon unit which undergoes reaction with the amidoxime 25. A wide variety of nitrile-containing functionalities are suitable (Scheme 17), and the reaction proceeds via the 2,3-dihydrooxadiazol-3-amine 31, so that the nitrile carbon forms the C5 position of the 1,2,4-oxadiazole.[‌6‌,‌80‌,‌109‌‌114‌] As shown in Scheme 17, a range of alkyl, aryl, and hetaryl nitriles react,[‌109‌,‌110‌] and the reaction is particularly effective in the presence of zinc chloride and hydrochloric acid.[‌110‌]

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References