Abstract
A facile arylation, alkenylation, and alkylation of functionalized 2-halopyridine N-oxides with various Grignard reagents was developed. It represented a highly efficient and selective C-H bond functionalization of pyridine derivatives in the presence of reactive C-Cl or C-Br bonds. Using Cl or Br as a blocking group, C2/C6 site-controllable functionalization of pyridine derivatives has been achieved. Various pyridine compounds can be prepared as illustrated in the total syntheses of Onychine, dielsine, and PARP-1 inhibitor GPI 16539.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkenes / chemistry*
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Alkylation
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Catalysis
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Cyclic N-Oxides / chemistry*
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Flavanones / chemical synthesis*
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Flavanones / chemistry
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Indicators and Reagents / chemistry*
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Molecular Structure
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Naphthyridines / chemical synthesis*
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Naphthyridines / chemistry
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Piperazines
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Piperidines / chemical synthesis*
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Piperidines / chemistry
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Pyridines / chemistry
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Pyridones / chemical synthesis*
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Pyridones / chemistry
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Stereoisomerism
Substances
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2-(4-methylpiperazin-1-yl)-5H-benzo(c)(1,5)naphthyridin-6-one
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Alkenes
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Cyclic N-Oxides
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Flavanones
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Indicators and Reagents
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Naphthyridines
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Piperazines
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Piperidines
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Pyridines
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Pyridones
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onychine