A metal-free and mild approach to 1,3,4-oxadiazol-2(3H)-ones via oxidative C-C bond cleavage using molecular oxygen

Bumhee Lim; Seunggun Park; Jae Hyun Park; Jongsik Gam; Sanghee Kim; Jung Woon Yang; Jeeyeon Lee

doi:10.1039/c7ob03188b

A metal-free and mild approach to 1,3,4-oxadiazol-2(3H)-ones via oxidative C-C bond cleavage using molecular oxygen

Org Biomol Chem. 2018 Mar 28;16(12):2105-2113. doi: 10.1039/c7ob03188b. Epub 2018 Mar 7.

Authors

Bumhee Lim¹, Seunggun Park¹, Jae Hyun Park¹, Jongsik Gam², Sanghee Kim¹, Jung Woon Yang³, Jeeyeon Lee¹

Affiliations

¹ College of Pharmacy, Research Institute of Pharmaceutical sciences, Seoul National University, 1 Gwanak-ro, Gwa-nak-gu, Seoul 08826, Korea. [email protected].
² Department of Medicinal Bioscience, College of Interdisciplinary & Creative Studies, Konyang University, 121 Daehak-ro, Nonsan, Chungnam, Korea.
³ Department of Energy Science, Sungkyunkwan University, Suwon 16419, South Korea.

PMID: 29511752
DOI: 10.1039/c7ob03188b

Abstract

A mild metal-free approach to 1,3,4-oxadiazol-2(3H)-ones via 1,3,4-oxadiazin-5(6H)-ones is described. This novel transformation, promoted by the electron-withdrawing p-substituents on the phenyl group at the α-carbonyl position, features a tandem reaction consisting of oxidative hydroxylation and C-C bond cleavage using molecular oxygen. The method utilizes K₂CO₃ in CH₃CN without any oxidants, transition metals, or additives, enabling the tunable synthesis of 1,3,4-oxadiazin-5(6H)-ones, 1,3,4-oxadiazol-2(3H)-ones, and α-ketoamides under mild aerobic conditions.