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利用重氮丙二烯通过直接催化光脱羧胺化反应将羧酸转化为多种含氮化合物。

Direct catalytic photodecarboxylative amination of carboxylic acids with diazirines for divergent access to nitrogen-containing compounds.

作者信息

Maharaj Vishala, Athawale Paresh R, Chandrachud Preeti P, Lopchuk Justin M

机构信息

Department of Chemistry, University of South Florida, Tampa, FL 33620, USA.

Drug Discovery Department, H. Lee Moffitt Cancer Center and Research Institute, 12902 Magnolia Drive, Tampa, FL 33612, USA.

出版信息

Cell Rep Phys Sci. 2024 Aug 21;5(8). doi: 10.1016/j.xcrp.2024.102103. Epub 2024 Jul 12.

Abstract

Amines, hydrazines, and nitrogen-containing heterocycles are pivotal species in medicine, agriculture, fine chemicals, and materials. Diazirines have been recently reported to serve as versatile electrophilic amination reagents for the synthesis of building blocks or late-stage C-N bond formation. Here, we report the catalytic photodecarboxylative amination of carboxylic acids with diazirines under mild conditions. The substrate scope includes broad functional group tolerance, such as ketones, esters, olefins, and alcohols, along with the late-stage amination of naproxen, ibuprofen, gemfibrozil, and gibberellic acid. Synthetic applications leverage the versatility of the intermediate diaziridines and include the regioselective preparation of a suite of 1-indazoles, 2-indazoles, and fluoroquinolones.

摘要

胺类、肼类和含氮杂环化合物是医药、农业、精细化学品和材料领域的关键物质。最近有报道称,重氮丙环可用作多功能亲电胺化试剂,用于合成结构单元或进行后期C-N键的形成。在此,我们报道了在温和条件下,羧酸与重氮丙环的催化光脱羧胺化反应。底物范围包括对多种官能团具有广泛耐受性,如酮、酯、烯烃和醇,以及萘普生、布洛芬、吉非贝齐和赤霉酸的后期胺化反应。合成应用利用了中间体二氮杂环丙烷的多功能性,包括一系列1-吲唑、2-吲唑和氟喹诺酮的区域选择性制备。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bd62/11500797/0655ed7192c4/nihms-2018501-f0002.jpg

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