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Updated: Jul 22, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Selective C-7 Functionalization of Phenanthridines by Microwave-Assisted Claisen Rearrangements of
Mathias Ryslett Lepsøe1, Aleksander Granum Dalevold1, Lise-Lotte Gundersen1
1Department of Chemistry, University of Oslo, P.O.Box 1033, Blindern, 0315, Oslo, Norway.
Abstract:
Carbon-carbon bond formation in the phenanthridine 7-position was achieved by microwave-assisted Claisen rearrangement of 8-allyloxyphenanthridines. The reactions took place with excellent regioselectivity and high chemical yields. If the 7-position was substituted, rearrangement to C-9 took place, but the reaction occurred less readily. Rearrangements of 8-allyloxy-5,6-dihydrophenanthridines (phenanthridines with a saturated B-ring) gave a mixture of 7- and 9-substituted products. The experimental results were supported by DFT (density functional theory) calculations.
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