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Updated: Jun 14, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Construction of 2,3-Naphthalimides through Cu-Catalyzed Decarboxylative Coupling between Arylpropiolic Acids and
Monty Kumar1,2, Prashant Kumar1,2, Ruchir Kant3
1Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031, India.
Abstract:
Herein, we report a one-pot strategy to synthesize functionalized 2,3-naphthalimides by a copper-catalyzed coupling between arylpropiolic acids and isocyanides followed by a dehydro-Diels-Alder (DDA) reaction. The reaction proceeds through the formation of an iminopropynyl-copper complex that accepts the second mole of acid, facilitating Mumm-type rearrangement to generate propioloyl-propiolamides that undergo DDA reaction. The method enables the synthesis of a wide range of 2,3-naphthalimides in a single step.
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