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Organic Chemistry Frontiers

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†

Zhong Zhang,a   Sirui Wu,a   Yuqiao Zhou, ORCID logo a   Bao-Lin Li,a   Siyue Xiao,a   Xiaohu Zhao*a  and  Zhipeng Yu ORCID logo *a  

* Corresponding authors

a Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China
E-mail: xhzhao@scu.edu.cn, zhipengy@scu.edu.cn

Abstract

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.

Graphical abstract: 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

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Article information

DOI
https://doi.org/10.1039/D4QO00463A
Article type
Research Article
Submitted
12 Mar 2024
Accepted
15 Apr 2024
First published
16 Apr 2024

Org. Chem. Front., 2024, Advance Article

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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

Z. Zhang, S. Wu, Y. Zhou, B. Li, S. Xiao, X. Zhao and Z. Yu, Org. Chem. Front., 2024, Advance Article , DOI: 10.1039/D4QO00463A

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