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A Study of the Reactions of 3-Bromopropenals with Anilines for the Synthesis of α-Bromo Enaminones
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2021-08-27 , DOI: 10.1002/adsc.202100779
Sundaram Suresh, Prakash Bhimrao Patil, Pao-Hsing Yu, Chia-Chi Fang, Yin-Zhi Weng, Veerababurao Kavala, Ching-Fa Yao

A one-pot strategy for the synthesis of α-bromo enaminones is reported. The reactions proceed via the p-toluenesulfonic acid monohydrate (TsOH ⋅ H2O) catalyzed reactions of 3-bromopropenals with anilines in dimethyl sulfoxide (DMSO) and does not require an external brominating agent. The chemoselective 1,2-addition was accomplished by employing aniline with a sterically hindered electron-withdrawing group attached at the ortho-position. In addition, the reactions involving other aniline derivatives as nucleophiles have resulted in minor yields of 1,4-addition product. The 3-bromopropenals showed a diverse range of reactivities with aniline derivatives.

中文翻译:

3-溴丙烯醛与苯胺反应合成α-溴烯胺酮的研究

报道了一种用于合成α-溴烯胺酮的一锅法。反应进行经由所述p -甲苯磺酸一水合物(加入TsOH⋅ħ 2 O)与在二甲亚砜(DMSO),并且不需要外部溴化剂苯胺3- bromopropenals催化的反应。化学选择性 1,2-加成是通过使用在位连接有位阻吸电子基团的苯胺来完成的。此外,涉及其他苯胺衍生物作为亲核试剂的反应导致 1,4-加成产物的产量很小。3-溴丙烯醛与苯胺衍生物表现出不同范围的反应性。
更新日期:2021-08-27
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