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Synthesis 2024; 56(09): 1465-1475
DOI: 10.1055/s-0042-1751555
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
Financial support for this work was partially provided by Chiang Mai University (Grant No. MRCMU2566R_016 to W.P.).
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 aminesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751555.
- Supporting Information
Publication History
Received: 06 December 2023
Accepted after revision: 17 January 2024
Article published online:
12 February 2024
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