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DOI: 10.1055/sos-SD-013-00175

Hemming, K.Science of Synthesis, (200413167.

Addition reactions to the 1,2,4-oxadiazole nucleus are rare and usually involve the complexation of a ring nitrogen by a metal. The successful isolation of the parent unsubstituted 1,2,4-oxadiazole involves the formation of a complex with cadmium chloride, from which the parent 1,2,4-oxadiazole is distilled at room temperature and reduced pressure.[‌13‌,‌169‌] Complexes with mercury[‌21‌,‌161‌] and with several transition metals are also known.[‌22‌,‌23‌] In a synthetically useful reaction, the N3 atom of several 1,2,4-oxadiazoles[‌1‌‌6‌] will quaternize, for example the amiloride prodrug 91 forms the oxadiazolium compound 92 (Scheme 42).[‌170‌]

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