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Visible-light-induced [1,3]-brook rearrangements of α-ketoacylsilanes and their subsequent trapping in a tandem annulation with 1,3,5-triazinanes and azomethine imines
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2024-04-16 , DOI: 10.1039/d4qo00463a
Zhong Zhang 1 , Sirui Wu 1 , Yuqiao Zhou 1 , Bao-Lin Li 1 , Siyue Xiao 1 , Xiaohu Zhao 1 , Zhipeng Yu 1
Affiliation  

An unusual visible-light-induced [1,3]-Brook rearrangement of α-ketoacylsilanes for cascade cyclization with 1,3,5-triazinanes and C,N-cyclic azomethine imines has been developed under catalyst-free and mild reaction conditions. The strategy offers an efficient and convenient approach for the rapid assembly of various β-lactams and pyrazolidinone scaffolds with structural and functional importance. Moreover, continuous-flow chemistry has been employed for two photochemical processes and gram-scale syntheses (up to 100 times) with comparable efficiency to batch conditions in a relatively short time, which allowed high-throughout synthesis and exhibited an increase in productivity.

中文翻译:

可见光诱导的 α-酮酰基硅烷的 [1,3]-布鲁克重排及其随后与 1,3,5-三嗪和甲亚胺亚胺的串联环化捕获

在无催化剂和温和的反应条件下,开发了一种不寻常的可见光诱导的 α-酮酰基硅烷的 [1,3]-布鲁克重排,用于与 1,3,5-三嗪和C , N-环状偶氮甲碱亚胺的级联环化。该策略为快速组装具有结构和功能重要性的各种β-内酰胺和吡唑烷酮支架提供了一种有效且方便的方法。此外,连续流化学已用于两种光化学过程和克级合成(高达100次),在相对较短的时间内具有与间歇条件相当的效率,这允许高通量合成并表现出生产率的提高。
更新日期:2024-04-16
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