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: togofaculty.chiba-u.jp

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

DOI: 10.1055/s-0039-1690102

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Abstract

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

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ID: J66-Y2019