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通过铑(III)催化未保护的芳基酰胺与3-重氮喹啉二酮的环化反应一锅法构建多样且功能化的异色满并喹啉二酮及其在荧光传感器中的应用

One-pot construction of diverse and functionalized isochromenoquinolinediones by Rh(iii)-catalyzed annulation of unprotected arylamides with 3-diazoquinolinediones and their application for fluorescence sensor.

作者信息

Shrestha Rajeev, Khanal Hari Datta, Lee Yong Rok

机构信息

School of Chemical Engineering, Yeungnam University Gyeongsan 38541 Republic of Korea

出版信息

RSC Adv. 2019 Jun 3;9(30):17347-17357. doi: 10.1039/c9ra03146d. eCollection 2019 May 29.

Abstract

A facile and efficient Rh(iii)-catalyzed annulation of arylamides with 3-diazoquinolinediones for the construction of diverse and highly functionalized isochromenoquinolinediones is described. Furthermore, the methodology is applicable for delivering various relevant molecules such as pyridopyranoquinolindiones, thienopyranoquinolinones, and indolopyranoquinolinone. The reaction proceeds cascade C-H activation, carbene insertion, and intramolecular lactonization. The reaction exhibits high atom economy, good functional group tolerance, and high regioselectivity. The synthesized compound can also behave as a potent fluorescence sensor for Fe ion.

摘要

描述了一种简便高效的铑(iii)催化芳基酰胺与3-重氮喹啉二酮的环化反应,用于构建多样且高度官能化的异色满并喹啉二酮。此外,该方法适用于合成各种相关分子,如吡啶并吡喃并喹啉二酮、噻吩并吡喃并喹啉酮和吲哚并吡喃并喹啉酮。该反应通过串联的C-H活化、卡宾插入和分子内内酯化进行。该反应具有高原子经济性、良好的官能团耐受性和高区域选择性。合成的化合物还可作为一种有效的铁离子荧光传感器。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/47d0/9064558/e81b186c9dc4/c9ra03146d-f1.jpg

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