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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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Article information


Submitted
01 Dec 2015
Accepted
31 Jan 2016
First published
01 Feb 2016

Med. Chem. Commun., 2016,7, 720-724
Article type
Research Article
Author version available

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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