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Synthesis 2024; 56(09): 1465-1475
DOI: 10.1055/s-0042-1751555
paper

Tertiary Amines as Temporary Masked Secondary Amines: A Direct Access to 5-Dialkylamino-1,2,4-oxadiazoles from 1,2,4-Oxadiazol-5(4H)-ones

Muh Alfliadhi
a   Department of Chemistry, 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
,
Surat Hongsibsong
b   Environmental, Occupational Health Sciences and Non Communicable Diseases Center of Excellence, Chiang Mai University, Chiang Mai 50200, Thailand
c   School of Health Science Research, Research Institute for Health Science, Chiang Mai University, Chiang Mai 50200, Thailand
,
Nittaya Wiriya
a   Department of Chemistry, 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
› InstitutsangabenFinancial support for this work was partially provided by Chiang Mai University (Grant No. MRCMU2566R_016 to W.P.).
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Abstract

A novel strategy utilizing tertiary amines as temporary masked secondary amines to synthesize 5-dialkylamino 1,2,4-oxadiazoles via Ph3P-I2 mediated amination of 1,2,4-oxadiazol-5(4H)-ones was developed. A one-step N-dealkylative functionalization of tertiary amines with the 1,2,4-oxadiazole ring enables a convenient access to diverse 5-amino-1,2,4-oxadiazoles. Additionally, orthogonally functionalized piperazine derivatives can be effectively constructed through site-selective reaction of 1,4-dialkylpiperazines or via a sequential N-functionalization of 1-methylpiperazine obviating laborious protection/deprotection steps.

Key words

1,2,4-oxadiazolones - 1,2,4-oxadiazoles - triphenylphosphine - iodine - amination - tertiary amines

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751555.
  • Supporting Information


Publikationsverlauf

Eingereicht: 06. Dezember 2023

Angenommen nach Revision: 17. Januar 2024

Artikel online veröffentlicht:
12. Februar 2024

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