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

Abstract

Various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylisoxazoles 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. Similarly, various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylpyrazoles in good yields in one pot by successive treatment with PhI(OAc)₂ in the presence of TEMPO, PhNHNH₂, and then NCS and decyl methyl sulfide, followed by reaction with alkynes in the presence of Et₃N. Thus, both 3-aryl- and 3-alkylisoxazoles, and 3-aryl- and 3-alkylpyrazoles could be prepared from readily available primary alcohols in one pot under transition-metal-free conditions.

Key words

isoxazole - pyrazole - alcohol - oxime - hydrazone - cycloaddition

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