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酸致变色实现喹喔啉酮与吲哚的氧化交叉偶联。

Oxidative cross-coupling of quinoxalinones with indoles enabled by acidochromism.

作者信息

Huang Jie, Wang Long, Tang Xiang-Ying

机构信息

Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, Hubei Engineering Research Center for Biomaterials and Medical Protective Materials, Hubei Key Laboratory of Bioinorganic Chemistry & Materia Medica, Semiconductor Chemistry Center, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology (HUST), Wuhan 430074, People's Republic of China.

出版信息

Org Biomol Chem. 2023 Mar 29;21(13):2709-2714. doi: 10.1039/d3ob00280b.

Abstract

An oxidative cross-coupling of quinoxalinones with indole derivatives B(CF)·HO induced acidochromism of quinoxalinone derivatives was developed under mild and external photocatalyst-free conditions. The reaction shows excellent substrate scope, accommodating a wide range of functional groups. The usefulness of this strategy was demonstrated by the synthesis of the natural products Azacephalandole A and Cephalandole A in high yields. Moreover, the products are fluorophores showing prevalent fluorescence properties with a wide emission range and good relative quantum yields.

摘要

喹喔啉酮与吲哚衍生物的氧化交叉偶联反应 在温和且无外部光催化剂的条件下,开发了B(CF)·HO诱导的喹喔啉酮衍生物的酸致变色反应。该反应具有出色的底物范围,能兼容多种官能团。通过高产率合成天然产物氮杂头孢菌素A和头孢菌素A证明了该策略的实用性。此外,产物是荧光团,具有普遍的荧光性质,发射范围宽且相对量子产率良好。

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