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: togo
faculty.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
ID: J66-Y2019
