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Updated: Dec 25, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Spontaneous oxidative cyclisations of 1,3-dihydroxy-4-dimethylallylnaphthalene to tricyclic derivatives
Jinglin Wang1, Huomiao Ran2, Xiulan Xie3
1Institut für Pharmazeutische Biologie und Biotechnologie, Philipps-Universität Marburg, Robert-Koch-Straße 4, 35037 Marburg, Germany. shuming.li@staff.uni-marburg.de and Union Hospital of Huazhong University of Science and Technology, Department of Pharmacy, No. 1227, Jiefang Road, 430030 Wuhan, China.
Abstract:
The attachment of a dimethylallyl moiety to C4 of 1,3-dihydroxynaphthalene led to spontaneous oxidative cyclisations, resulting in the formation of two tetrahydrobenzofuran and one bicyclo[3.3.1]nonane derivatives. Incubation under an 18O-rich atmosphere proved that both the incorporated oxygen atoms originated from O2. A radical-involved mechanism is proposed for these cyclisations.
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