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

Takashi Okitsu; Kana Sato; Taterao M. Potewar; Akimori Wada

doi:10.1021/jo200407b

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

Takashi Okitsu, Kana Sato, Taterao M. Potewar, Akimori Wada^*

^*この論文の責任著者

分子合成化学研究室

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

51 被引用数 (Scopus)

抄録

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.

本文言語	英語
ページ（範囲）	3438-3449
ページ数	12
ジャーナル	Journal of Organic Chemistry
巻	76
号	9
DOI	https://doi.org/10.1021/jo200407b
出版ステータス	出版済み - 2011/05/06

ASJC Scopus 主題領域

有機化学

文献へのアクセス

10.1021/jo200407b

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引用スタイル

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abstract = "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.",

author = "Takashi Okitsu and Kana Sato and Potewar, {Taterao M.} and Akimori Wada",

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AU - Wada, Akimori

PY - 2011/5/6

Y1 - 2011/5/6

N2 - 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.

AB - 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.

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