Late Stage CH Activation of a Privileged Scaffold; Synthesis of a Library of Benzodiazepines

A library of over twenty 5‐(2‐arylphenyl)‐1,3‐dihydro‐2H‐1,4‐benzodiazepin‐2‐ones has been formed by a microwave‐mediated late‐stage palladium‐catalysed arylation of 1,4‐benzodiazepines using diaryliodonium salts. This can also be applied to nordazepam (7‐chloro‐5‐phenyl‐1,3‐dihydro‐2H‐1,4‐benzodiaz...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2016-01, Vol.358 (1), p.98-109
Main Authors: Khan, Raysa, Felix, Robert, Kemmitt, Paul D., Coles, Simon J., Day, Iain J., Tizzard, Graham J., Spencer, John
Format: Article
Language:English
Subjects:
Activation
Benzodiazepines
Catalysis
CH activation
deuteration
Exchange
heterocycles
Libraries
Metabolites
microwaves
palladium
Scaffolds
Synthesis
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Summary:A library of over twenty 5‐(2‐arylphenyl)‐1,3‐dihydro‐2H‐1,4‐benzodiazepin‐2‐ones has been formed by a microwave‐mediated late‐stage palladium‐catalysed arylation of 1,4‐benzodiazepines using diaryliodonium salts. This can also be applied to nordazepam (7‐chloro‐5‐phenyl‐1,3‐dihydro‐2H‐1,4‐benzodiazepin‐2‐one), the active metabolite of diazepam, and subsequent N‐alkylation and/or H/D exchange allows further diversification towards elaborated pharmaceuticals and their 3,3′‐deuterated analogues.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201501009