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Updated: Sep 12, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
NaOH-Mediated Intermolecular Cascade Cyclization Reaction of Conjugated Dieneimines with α-Halomalonates to Access
Kai-Kai Wang1, Qing Xu1, Liang-Man Wu1
1School of Pharmacy, Xinxiang University, 453000 Xinxiang, P. R. China.
Abstract:
An efficient intermolecular cascade cyclization of conjugated dieneimines with α-halomalonates in the presence of a NaOH base was developed. This method facilitates the synthesis of a diverse range of functionalized cyclopentenes featuring two adjacent stereocenters, including a quaternary carbon center, in high yields with excellent diastereoselectivities and perfect regioselectivities. The reaction proceeds through a sequence of Michael addition, cyclopropanation, isomerization, ring opening of the cyclopropane intermediate, isomerization, and intramolecular cyclization. Furthermore, the practical utility of this methodology is demonstrated through its application in subsequent synthetic transformations and late-stage functionalization of drug molecules. Additionally, a molecular docking study was conducted to investigate the potential biological activity of the products.
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