title: Palladium-Catalyzed Oxidative O-H/N-H Carbonylation of Hydrazides: Access to Substituted 1,3,4-Oxadiazole-2(3H)-ones.
abstract: A novel palladium-catalyzed oxidative annulation reaction for the C-O, C-N bond formations is developed. The intramolecular cyclocarbonylation provides an efficient and direct approach for the construction of valuable 1,3,4-oxadiazole-2(3H)-ones and their derivatives. The reaction also facilitated the convenient synthesis of BMS-191011, an opener of the cloned large-conductance Ca(2+)-activated potassium channel, providing an attractive method for medicinal chemistry.
authors.affiliation: School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China.
authors.forename: Fanghua
authors.initials: F
authors.lastname: Ji
authors.affiliation: School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China.
authors.forename: Xianwei
authors.initials: X
authors.lastname: Li
authors.affiliation: School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China.
authors.forename: Wei
authors.initials: W
authors.lastname: Guo
authors.affiliation: School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China.
authors.forename: Wanqing
authors.initials: W
authors.lastname: Wu
authors.affiliation: School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China.
authors.forename: Huanfeng
authors.initials: H
authors.lastname: Jiang
mesh_terms: D002384:Catalysis; D002626:Chemistry, Pharmaceutical; D003500:Cyclization; D006834:Hydrazines / Q000737:chemistry*; D015394:Molecular Structure; D010069:Oxadiazoles / Q000138:chemical synthesis / Q000737:chemistry*; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry; D015221:Potassium Channels / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C480883:3-((5-chloro-2-hydroxyphenyl)methyl)-5-(4-(trifluoromethyl)phenyl)-1,3,4-oxadiazol-2(3H)-one; D006834:Hydrazines; D010069:Oxadiazoles; D015221:Potassium Channels; D010165:Palladium