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Application of N‑Acylbenzotriazoles in the Synthesis of 5‑Substituted 2‑Ethoxy-1,3,4-oxadiazoles as Building Blocks toward 3,5-Disubstituted 1,3,4-Oxadiazol-2(3H)‑ones

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journal contribution
posted on 01.09.2017, 18:08 by Sirawit Wet-osot, Wong Phakhodee, Mookda Pattarawarapan
5-Substituted-2-ethoxy-1,3,4-oxadiazoles were conveniently prepared through a one-pot sequential N-acylation/dehydrative cyclization between ethyl carbazate and N-acylbenzotriazoles in the presence of Ph3P–I2 as a dehydrating agent. Subsequent treatment with a stoichiometric amount of alkyl halides (X = Cl, Br, I) enables a rapid access to a variety of 3,5-disubstituted 1,3,4-oxadiazol-2­(3H)-ones in good to excellent yields.