Organocatalytic Oxidative Cyclization of Amidoximes for the Synthesis of 1,2,4‐Oxadiazolines

Organocatalytic synthesis of bi‐ and tricyclic fused 1,2,4‐oxadiazolines is reported. The reaction proceeds through oxidative cyclization of the corresponding amidoxime using 2,4,6‐tris(4‐fluorophenyl)pyrylium tetrafluoroborate (T(p‐F)PPT) as the organocatalyst, and molecular oxygen as the green oxi...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2018-07, Vol.360 (14), p.2626-2631
Main Authors: Soni, Vineet Kumar, Kim, Jun, Cho, Eun Jin
Format: Article
Language:English
Subjects:
Cyclization
Molecular chains
Molecular oxygen
Nitrogen heterocycles
Organocatalysis
Oxygen
Synthesis
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Summary:Organocatalytic synthesis of bi‐ and tricyclic fused 1,2,4‐oxadiazolines is reported. The reaction proceeds through oxidative cyclization of the corresponding amidoxime using 2,4,6‐tris(4‐fluorophenyl)pyrylium tetrafluoroborate (T(p‐F)PPT) as the organocatalyst, and molecular oxygen as the green oxidant. During the transformation, T(p‐F)PPT acts as both the electrophilic catalyst and photocatalyst, and the reaction is promoted by irradiation with visible light. The method introduced herein offers a straightforward route to the preparation of 1,2,4‐oxadiazolines with different functionalities, and is highly atom economical.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201800238