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