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Issue 4, 2016
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Continuous flow photochemistry as an enabling synthetic technology: synthesis of substituted-6(5H)-phenanthridinones for use as poly(ADP-ribose) polymerase inhibitors

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Abstract

Methods utilizing continuous flow photochemistry, an enabling synthetic technology, have been developed for the generation of phenanthridinones via an intramolecular photochemical cyclization of 2-chlorobenzamides for the purposes of generating poly(ADP-ribose) polymerase inhibitors. Herein we report 16 examples of a single-step flow photocyclization which produces substituted phenanthridinones in yields up to 99%, while a two-step method leads directly to phenanthridinones from 2-chlorobenzoyl chlorides and anilines via a novel continuous flow amidation/photocyclization protocol. Overall, the flow photocyclization reactions typically progress in good to excellent yields, and in a superior fashion to analogous batch methods, greatly enabling the drug discovery process.

Graphical abstract: Continuous flow photochemistry as an enabling synthetic technology: synthesis of substituted-6(5H)-phenanthridinones for use as poly(ADP-ribose) polymerase inhibitors

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Publication details

The article was received on 01 Dec 2015, accepted on 31 Jan 2016 and first published on 01 Feb 2016


Article type: Research Article
DOI: 10.1039/C5MD00552C
Author version available: Download Author version (PDF)
Citation: Med. Chem. Commun., 2016,7, 720-724
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    Continuous flow photochemistry as an enabling synthetic technology: synthesis of substituted-6(5H)-phenanthridinones for use as poly(ADP-ribose) polymerase inhibitors

    Y. Fang and G. K. Tranmer, Med. Chem. Commun., 2016, 7, 720
    DOI: 10.1039/C5MD00552C

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