Solid-Phase N-Electrophilic Amination of 2-Aminopyridines: Preparation of 2-Substituted-[1,2,4]triazolo[1,5-a]pyridine Derivatives

Solid‐phase N‐amination of 2‐aminopyridin‐3/5‐yl derivatives supported via an acid labile linker by hydroxylamine‐based electrophilic NH2+ equivalents is described. A comparison of aminating efficiency and stability between O‐Mesitylenesulfonyl Hydroxylamine (MSH) (5) and O‐(2,4‐Dinitrophenyl)hydrox...

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Bibliographic Details
Published in:QSAR & combinatorial science 2006-10, Vol.25 (10), p.961-965
Main Authors: Fernàndez, Joan-Carles, Solé-Feu, Laia, Fernández-Forner, Dolors, de la Figuera, Natalia, Forns, Pilar, Albericio, Fernando
Format: Article
Language:English
Subjects:
4-dinitrophenyl)hydroxylamine
N-amination
O-mesitylenesulfonyl hydroxylamine
O‐(2,4‐dinitrophenyl)hydroxylamine
Solid-phase organic synthesis
Triazolopyridines
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Summary:Solid‐phase N‐amination of 2‐aminopyridin‐3/5‐yl derivatives supported via an acid labile linker by hydroxylamine‐based electrophilic NH2+ equivalents is described. A comparison of aminating efficiency and stability between O‐Mesitylenesulfonyl Hydroxylamine (MSH) (5) and O‐(2,4‐Dinitrophenyl)hydroxylamine (Dnp‐ONH2) (8) on solid‐phase is also reported. A practical two‐step preparation of 2‐substituted‐[1,2,4]triazolo[1,5‐a]pyridin‐6/8‐yl derivatives (4) on solid‐phase using this methodology gave compounds in good purity and yields.
ISSN:1611-020X
1611-0218
DOI:10.1002/qsar.200520170