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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
a   Department of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand
,
Subin Jaita
b   Faculty of Science and Agricultural Technology, Rajamangala University of Technology Lanna Chiang Rai, Chiang Rai 57120, Thailand
c   Center of Excellence in Materials Science and Technology, Chiang Mai University, Chiang Mai 50200, Thailand
,
Surat Hongsibsong
d   School of Health Science Research, Research Institute for Health Science, Chiang Mai University, Chiang Mai 50200, Thailand
,
Saranphong Yimklan 
a   Department of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand
e   Research Center on Chemistry for Development of Health Promoting Products from Northern Resources, Faculty of Science, Chiang Mai University, Chiang Mai, 50200, Thailand
,
Wong Phakhodee 
a   Department of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand
e   Research Center on Chemistry for Development of Health Promoting Products from Northern Resources, Faculty of Science, Chiang Mai University, Chiang Mai, 50200, Thailand
,
Mookda Pattarawarapan∗
a   Department of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand
c   Center of Excellence in Materials Science and Technology, Chiang Mai University, Chiang Mai 50200, Thailand
e   Research Center on Chemistry for Development of Health Promoting Products from Northern Resources, Faculty of Science, Chiang Mai University, Chiang Mai, 50200, Thailand
› Author AffiliationsFinancial support for this study was provided by The Thailand Research Fund through the Royal Golden Jubilee (RGJ) Ph.D. Programme (Grant No. PHD/0023/2559 to D.Y.). This research work was partially supported by Chiang Mai University, Thailand.
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1874-6399.
  • Supporting Information


Publication History

Received: 19 May 2022

Accepted after revision: 13 June 2022

Accepted Manuscript online:
13 June 2022

Article published online:
20 July 2022

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