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Updated: Jul 30, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Photoinduced Minisci Reaction with Diazines: An Approach Toward Original Fused Heterocycles
Marie Auvray1, Matthieu Jeanty2, Philippe Jubault1
1NSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), Normandie Univ., 76000, Rouen, France.
Abstract:
Herein, we developed a photoinduced Minisci reaction on a large panel of diazines with good to excellent yields (28 examples, 44 % to 89 %). The reaction using 4CzIPN (1 mol %) as photoinitiator was carried out under white LED irradiation and required a slight excess of the acid reagent (1.2 equiv.). Cyclization reactions were then developed to access original N-heterocycles building blocks for drug discovery programs. An extension of the reaction to continuous flow was also reported. Finally, the mechanism of the transformation was studied suggesting a plausible radical chain mechanism.
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