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Facile One-Pot Transformation of Primary Alcohols into 3-Aryl- and 3-Alkyl-isoxazoles and -pyrazoles

Eiji Kobayashi, Hideo Togo*

*Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan, Email:

E. Kobayashi, H. Togo, Synthesis, 2019, 51, 3723-3735.

DOI: 10.1055/s-0039-1690102

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Various primary alcohols were smoothly transformed into 3-substitued isoxazoles in good yields in one pot by successive treatment with PhI(OAc)2 in the presence of TEMPO, NH2OH, and then NCS, followed by reaction with alkynes in the presence of Et3N. The use of PhNHNH2 instead of NH2OH and decyl methyl sulfide as additive in later step enabled the synthesis of pyrazoles.

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Key Words

isoxazoles, pyrazoles, alcohols, oximes, hydrazones, cycloaddition, PhI(OAc)2, NCS

ID: J66-Y2019