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Updated: Oct 25, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Ambient Synthesis of Tricyclic Naphthalenes via Stepwise Styryl-yne Dearomative Diels-Alder Cyclization
Nicola Camedda1, Matteo Lanzi1, Franca Bigi1,2
1Università di Parma, Department of Chemistry, Life Sciences and Environmental Sustainability, Parco Area delle Scienze 17/A, 43124 Parma, Italy.
Abstract:
A cascade of styrylynols promoted by MnO2 allows the synthesis of fused tricycles with a naphthalene core. The reaction occurs under ambient conditions, offering a practical synthetic tool because of the inexpensive and abundant manganese species. The method affords products through the sequential oxidation of a propargyl alcohol, stepwise Diels-Alder cyclization, and finally rearomatization. According to density functional theory, the usually unfavorable stepwise Diels-Alder mechanism is instead a general tool for eliciting otherwise challenging dearomative annulation.
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