稠合多环1,6-萘啶-4-胺的温和合成及其光学性质。

Mild synthesis of fused polycyclic 1,6-naphthyridin-4-amines and their optical properties.

作者信息

Li Ze, Zhang Dongfeng, Wang Hanxun, Huang Haihong, Cheng Maosheng, Zhao Hongyi

机构信息

Key Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, School of Pharmaceutical Engineering, Shenyang Pharmaceutical University Shenyang 110016 Liaoning P. R. China

Beijing Key Laboratory of Active Substance Discovery and Druggability Evaluation, Chinese Academy of Medical Sciences Key Laboratory of Anti-DR TB Innovative Drug Research, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences 1 Xian Nong Tan Street Beijing 100050 P. R. China

出版信息

RSC Adv. 2025 Aug 1;15(34):27551-27557. doi: 10.1039/d5ra03301b.

DOI:10.1039/d5ra03301b

PMID:40756659

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12315796/

Abstract

A mild and straightforward synthetic route to tri-, tetra-, and pentacyclic 1,6-naphthyridin-4-amines is presented. The protocol involves CFSOH- or HSO-mediated Friedel-Crafts-type intramolecular cycloaromatisation of 4-(arylamino)nicotinonitriles in which the cyano group acts as a one-carbon synthon. The transformation achieves good to excellent yields and can be performed on a gram scale. Additionally, the exploration of fluorescence properties of these compounds demonstrates their potential application as fluorophores.

摘要

本文介绍了一种温和且直接的合成三、四和五环1,6-萘啶-4-胺的路线。该方法涉及CFSOH或HSO介导的4-(芳基氨基)烟腈的傅克型分子内环芳构化反应，其中氰基作为一碳合成子。该转化反应产率良好至优异，且可进行克级规模的反应。此外，对这些化合物荧光性质的研究表明它们作为荧光团具有潜在应用价值。