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

doi:10.1016/j.tetlet.2016.07.082

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

Medicinal Chemistry

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

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 language	English (US)
Pages (from-to)	4056-4060
Number of pages	5
Journal	Tetrahedron Letters
Volume	57
Issue number	36
DOIs	https://doi.org/10.1016/j.tetlet.2016.07.082
State	Published - 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

Keywords

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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10.1016/j.tetlet.2016.07.082

http://europepmc.org/articles/pmc5271595

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

abstract = "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.",

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

author = "Breunig, {Stephanie L.} and Olson, {Margaret E.} and Harki, {Daniel A.}",

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: {\textcopyright} 2016 Elsevier Ltd",

year = "2016",

doi = "10.1016/j.tetlet.2016.07.082",

language = "English (US)",

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AU - Olson, Margaret E.

AU - Harki, Daniel A.

N1 - 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

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AB - 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.

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

Abstract

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