tert-Butyl Nitrite Mediated Synthesis of 1,2,4-Oxadiazol-5(4H)-ones from Terminal Aryl Alkenes,Organic Letters

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tert-Butyl Nitrite Mediated Synthesis of 1,2,4-Oxadiazol-5(4H)-ones from Terminal Aryl Alkenes
Organic Letters ( IF 4.9 ) Pub Date : 2019-06-17 00:00:00 , DOI: 10.1021/acs.orglett.9b01430
Prasenjit Sau ₁ , Amitava Rakshit ₁ , Tipu Alam ₁ , Hemant Kumar Srivastava ₁ , Bhisma K. Patel ₁

Affiliation

tert-Butyl nitrite (TBN) mediated synthesis of 3-aryl-1,2,4-oxadiazol-5(4H)-ones has been accomplished using terminal aryl alkenes via a biradical reaction intermediate. Three consecutive sp² C–H bond functionalizations of styrenes afforded 3-phenyl-1,2,4-oxadiazol-5(4H)-ones via the formation of new C═N, C═O, C–O, and two C–N bonds. Both of the N atoms originate from TBN, while the carbonyl oxygen is from the water (moisture) the other oxygen from the N═O part of the TBN.

中文翻译：

亚硝酸叔丁酯介导的由末端芳基烯烃合成1,2,4-恶二唑-5（4 H）-的合成

已使用末端芳基烯烃通过双自由基反应中间体完成了亚硝酸叔丁酯（TBN）介导的3-芳基-1,2,4-恶二唑-5（4 H）-的合成。苯乙烯的三个连续的sp ² C–H键官能化通过形成新的C═N，C═O，C–O和两个生成3-苯基-1,2,4-恶二唑-5（4 H）-一。 C–N键。N个原子都来自TBN，而羰基氧则来自水（水分），其他氧则来自TBN的N = O部分。

更新日期：2019-06-17

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