Smiles Rearrangement as a Tool for the Preparation of Dihydrodipyridopyrazines

A novel methodology for the synthesis of isomer A of dihydrodipyridopyrazines was developed. The key transformation features a Smiles rearrangement of nitro substituted N,N′-dipyridinylamines, potential precursors of isomer B obtained by the alkylation of compounds prepared by a Pd-catalyzed reactio...

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Bibliographic Details
Published in:Organic letters 2009-12, Vol.11 (23), p.5502-5505
Main Authors: Patriciu, Oana-Irina, Fînaru, Adriana-Luminita, Massip, Stéphane, Leger, Jean-Michel, Jarry, Christian, Guillaumet, Gérald
Format: Article
Language:English
Subjects:
Alkylation
Catalysis
Cyclization
Heterocyclic Compounds, 3-Ring - chemical synthesis
Heterocyclic Compounds, 3-Ring - chemistry
Molecular Structure
Pyrazines - chemical synthesis
Pyrazines - chemistry
Pyridines - chemical synthesis
Pyridines - chemistry
Stereoisomerism
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Summary:A novel methodology for the synthesis of isomer A of dihydrodipyridopyrazines was developed. The key transformation features a Smiles rearrangement of nitro substituted N,N′-dipyridinylamines, potential precursors of isomer B obtained by the alkylation of compounds prepared by a Pd-catalyzed reaction and subsequent cyclization.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol902369v