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Updated: Jun 23, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Intramolecular Dehydrogenative Photocyclization of N-Phenyl-1-naphthamides
Hao-Yuan Li1, Xiaoying Niu1, Shan-Shan Zhang1
1Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, State Key Laboratory of New Pharmaceutical Preparations and Excipients, Hebei Research Center of the Basic Discipline of Synthetic Chemistry, Key Laboratory of Chemical Biology of Hebei Province (22567635H), College of Chemistry and Materials Science, Hebei University, Baoding 071002, P. R. China.
Abstract:
Here, we explore a dehydrogenative 6π photocyclization method for N-substituted naphthalene carboxamides, which can be conducted in air. This method employs DMSO as both the reaction solvent and oxidant while also stabilizing the excited state of the substrate. Furthermore, the addition of photosensitizer enables the reaction to proceed under a 440-445 nm LED source via energy transfer. The proposed mechanism is initially validated through DFT calculations.
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