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通过连续光点击反应构建结构多样的富氮骨架

Structurally Diverse Nitrogen-Rich Scaffolds via Continuous Photo-Click Reactions.

作者信息

Cronly Davin, Smyth Megan, Moody Thomas S, Wharry Scott, Bruno-Colmenarez Julia, Twamley Brendan, Baumann Marcus

机构信息

School of Chemistry, University College Dublin, O'Brien Centre for Science, Belfield, Dublin 4, Ireland.

Technology Department, Almac Sciences, Craigavon, BT63 5QD, U.K.

出版信息

Org Lett. 2024 Dec 13;26(49):10559-10563. doi: 10.1021/acs.orglett.4c03953. Epub 2024 Nov 26.

Abstract

Continuous flow technology was exploited for the effective generation of nitrile imines via photolysis of substituted aryl tetrazoles. The resulting photo-click process rapidly affords advanced nitrogen-rich scaffolds upon the subsequent trapping of the reactive dipole with alkenes, alkynes, and benzylic amines. Crucially, this approach uncovers the differential reactivity for ether vs amine tethers, thus providing facile and scalable access to underexplored medicinally relevant heterocyclic entities.

摘要

连续流动技术被用于通过取代芳基四唑的光解有效地生成腈亚胺。随后,通过将反应性偶极与烯烃、炔烃和苄胺捕获,由此产生的光点击过程迅速提供了先进的富氮支架。至关重要的是,这种方法揭示了醚键和胺键的不同反应性,从而为探索不足的与医学相关的杂环实体提供了简便且可扩展的途径。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/730f/11650770/7ef9ca6d0532/ol4c03953_0003.jpg

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