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Updated: Sep 13, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Mild synthesis of fused polycyclic 1,6-naphthyridin-4-amines and their optical properties
Ze Li1,2, Dongfeng Zhang2, Hanxun Wang1
1Key Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, School of Pharmaceutical Engineering, Shenyang Pharmaceutical University Shenyang 110016 Liaoning P. R. China mscheng@syphu.edu.cn.
Abstract:
A mild and straightforward synthetic route to tri-, tetra-, and pentacyclic 1,6-naphthyridin-4-amines is presented. The protocol involves CF3SO3H- or H2SO4-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.
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