Rapid, microwave accelerated synthesis of [1,2,4]triazolo[3,4-b][1,3,4]oxadiazoles from 4-acylamino-1,2,4-triazoles

Stephanie L. Breunig, Margaret E. Olson, Daniel A. Harki

Research output: Contribution to journalArticlepeer-review

5 Scopus citations


1,2,4-Triazoles and 1,3,4-oxadiazoles are prevalent moieties in pharmaceutical agents, yet fused [1,2,4]triazolo[3,4-b][1,3,4]oxadiazoles are surprisingly under-represented for both synthesis and biological application. We report a rapid, two-step synthesis of [1,2,4]triazolo[3,4-b][1,3,4]oxadiazoles from commercial 4-amino-1,2,4-triazoles that is highlighted by a microwave accelerated intramolecular cyclization to generate the fused ring system. Our efforts to optimize reaction conditions and elucidate reaction mechanism are also described.

Original languageEnglish (US)
Pages (from-to)4056-4060
Number of pages5
JournalTetrahedron Letters
Issue number36
StatePublished - 2016

Bibliographical note

Funding Information:
We gratefully acknowledge funding by the National Institutes of Health ( R01-GM110129 ) and the University of Minnesota , Office of the Vice President for Research (Equipment Grant-in-Aid to purchase the CEM Discover SP Microwave Synthesizer). S.L.B. thanks the University of Minnesota, Undergraduate Research Opportunities Program (UROP) and the Department of Chemistry Heisig/Gleysteen Summer Undergraduate Research Fellowship Program for financial support. M.E.O. acknowledges the National Institutes of Health for a Ruth L. Kirschstein NRSA Predoctoral Fellowship (F31-CA183246). Mass spectrometry was performed at the Analytical Biochemistry Core Facility of the Masonic Cancer Center (University of Minnesota), which is supported in part by the National Institutes of Health (P30-CA77598).

Publisher Copyright:
© 2016 Elsevier Ltd


  • 1,2,4-Triazole
  • 1,3,4-Oxadiazole
  • Intramolecular cyclization
  • Microwave chemistry
  • [1,2,4]Triazolo[3,4-b][1,3,4]oxadiazole


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