Iodocyclization of hydroxylamine derivatives based on the control of oxidative aromatization leading to 2, 5-dihydroisoxazoles and isoxazoles

T Okitsu, K Sato, TM Potewar…

文献索引：Okitsu, Takashi; Sato, Kana; Potewar, Taterao M.; Wada, Akimori Journal of Organic Chemistry, 2011 , vol. 76, # 9 p. 3438 - 3449

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被引用次数: 29

摘要

An efficient method for the synthesis of 2, 5-dihydroisoxazoles and isoxazoles using iodocyclization of N-alkoxycarbonyl O-propargylic hydroxylamines has been developed. 2, 5- Dihydro-4-iodoisoxazole underwent the cross-coupling reactions without aromatization to afford polyfunctionalized 2, 5-dihydroisoxazoles. This process was applied to the preparation of valdecoxib and its 2, 5-dihydro-derivative.