Iron-mediated deuterium addition cascade cyano insertion/cyclization of -arylacrylamides to access deuterium-labelled phenanthridines

Deuterated molecules feature important biological activities and pharmacokinetic properties for the design of pharmaceuticals. Radical cyclization cascades involving the deuteration of alkenes to form heterocyclic compounds have rarely been reported. Herein, a deuterium addition cascade cyano insert...

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Veröffentlicht in:Organic & biomolecular chemistry 2020-08, Vol.18 (31), p.6126-6133
Hauptverfasser: Ji, Lei, Gu, Weijin, Liu, Ping, Sun, Peipei
Format: Artikel
Sprache:eng
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Zusammenfassung:Deuterated molecules feature important biological activities and pharmacokinetic properties for the design of pharmaceuticals. Radical cyclization cascades involving the deuteration of alkenes to form heterocyclic compounds have rarely been reported. Herein, a deuterium addition cascade cyano insertion/cyclization of N -arylacrylamides to synthesize deuterated phenanthridines is described. Cheap Fe(NO 3 ) 3 ·9H 2 O enables the generation of a deuterium radical from NaBD 4 in situ . These reactions proceed under mild conditions in a short time and a variety of functional groups are well tolerated. Deuterated molecules feature important biological activities and pharmacokinetic properties for the design of pharmaceuticals.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob01178a