5-Amino-Substituted 2-Methoxy-1,3,4-oxadiazoles as Common Precursors Toward 1,3,4-Oxadiazol-2(3H)-ones and 1,2,4-Triazolidine-3,5-diones

Dolnapa Yamano; Subin Jaita; Surat Hongsibsong; Saranphong Yimklan; Wong Phakhodee; Mookda Pattarawarapan

doi:10.1055/a-1874-6399

Synthesis, Table of Contents

Synthesis 2022; 54(20): 4539-4550
DOI: 10.1055/a-1874-6399

paper

5-Amino-Substituted 2-Methoxy-1,3,4-oxadiazoles as Common Precursors Toward 1,3,4-Oxadiazol-2(3H)-ones and 1,2,4-Triazolidine-3,5-diones

Dolnapa Yamano

^aDepartment of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand

,

Subin Jaita

^bFaculty of Science and Agricultural Technology, Rajamangala University of Technology Lanna Chiang Rai, Chiang Rai 57120, Thailand

^cCenter of Excellence in Materials Science and Technology, Chiang Mai University, Chiang Mai 50200, Thailand

,

Surat Hongsibsong

^dSchool of Health Science Research, Research Institute for Health Science, Chiang Mai University, Chiang Mai 50200, Thailand

,

Saranphong Yimklan

^aDepartment of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand

^eResearch Center on Chemistry for Development of Health Promoting Products from Northern Resources, Faculty of Science, Chiang Mai University, Chiang Mai, 50200, Thailand

,

Wong Phakhodee

^aDepartment of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand

^eResearch Center on Chemistry for Development of Health Promoting Products from Northern Resources, Faculty of Science, Chiang Mai University, Chiang Mai, 50200, Thailand

,

Mookda Pattarawarapan∗

^aDepartment of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand

^cCenter of Excellence in Materials Science and Technology, Chiang Mai University, Chiang Mai 50200, Thailand

^eResearch Center on Chemistry for Development of Health Promoting Products from Northern Resources, Faculty of Science, Chiang Mai University, Chiang Mai, 50200, Thailand

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Abstract

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Abstract

The divergent synthesis of two different classes of azole derivatives using 5-amino-substituted 2-methoxy-1,3,4-oxadiazoles as common substrates is reported. Depending on the reaction time and temperature, alkylation of oxadiazoles with excess alkyl halides proceeds with high regioselectivity toward 1,3,4-oxadiazolones and 1,2,4-triazolidine-3,5-diones. This operationally simple protocol enables rapid access to a diverse set of isomeric azoles using minimum synthetic steps and easily accessible oxadiazole key precursors.

Key words

1,3,4-oxadiazoles - 1,3,4-oxadiazolones - 1,2,4-triazolidine-3,5-diones - triphenylphosphine - trichloroisocyanuric acid

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References

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Supporting Information