Late stage C-H activation of a privileged scaffold; synthesis of a library of benzodiazepines
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-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.
98-109
Khan, Raysa
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Felix, Robert
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Kemmitt, Paul D.
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Coles, Simon
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Day, Iain J.
63855d2b-1a0e-485e-b84f-9c1a6bca9a0e
Tizzard, Graham
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Spencer, John
a3cf55cd-a4c7-4af6-b16c-96c8fb8c4cf4
7 January 2016
Khan, Raysa
ac317732-8e4c-4571-88b3-3b3f2372cec7
Felix, Robert
acfd9272-cc4b-4838-bca1-8c31965d5a2e
Kemmitt, Paul D.
0f178e56-e8e2-4d3d-b8af-71d0f5641f19
Coles, Simon
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Day, Iain J.
63855d2b-1a0e-485e-b84f-9c1a6bca9a0e
Tizzard, Graham
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Spencer, John
a3cf55cd-a4c7-4af6-b16c-96c8fb8c4cf4
Khan, Raysa, Felix, Robert, Kemmitt, Paul D., Coles, Simon, Day, Iain J., Tizzard, Graham and Spencer, John
(2016)
Late stage C-H activation of a privileged scaffold; synthesis of a library of benzodiazepines.
Advanced Synthesis & Catalysis, 358 (1), .
(doi:10.1002/adsc.201501009).
Abstract
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.
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Late Stage CCH Activation of a Privileged Scaffold; Synthesis of a Library of Benzodiazepines.pdf
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e-pub ahead of print date: 5 January 2016
Published date: 7 January 2016
Identifiers
Local EPrints ID: 393077
URI: http://eprints.soton.ac.uk/id/eprint/393077
ISSN: 1615-4150
PURE UUID: ace705ce-883f-4c2e-95d3-6265305b787b
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Date deposited: 21 Apr 2016 09:43
Last modified: 15 Mar 2024 03:10
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Author:
Raysa Khan
Author:
Robert Felix
Author:
Paul D. Kemmitt
Author:
Iain J. Day
Author:
John Spencer
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