4.7 Article

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

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 18, Pages 9923-9929

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b01863

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Funding

  1. Center of Excellence for Innovation in Chemistry (PERCH-CIC), Office of the Higher Education Commission, Ministry of Education, Thailand
  2. Center of Excellence in Materials Science and Technology under the administration of Materials Science Research Center, Faculty of Science, Chiang Mai University

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5-Substituted-2-ethox-y-1,3,4-oxadiazoks were conveniently prepared through a one-pot sequential N-acylation/dehydrative cyclization between ethyl carbazate and N-acylbenzotriazoles in the presence of Ph3P-I-2 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.

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