4.5 Review

Pyridones - Powerful Precursors for the Synthesis of Alkaloids, Their Derivatives, and Alkaloid-Inspired Compounds

Journal

SYNTHESIS-STUTTGART
Volume 51, Issue 18, Pages 3369-3396

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1611844

Keywords

2-pyridone; piperidines; pyridines; alkaloids; ring closure; natural products; fused-ring systems; bridged-ring systems

Funding

  1. Narodowe Centrum Nauki (NCN, National Science Center, Poland) [2016/23/N/ST5/00101]

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2-Pyridone is characterized by a very wide range of reactivity of a different nature, ranging from electrophilic aromatic substitution, CH-metal-mediated reactions, and NH/OH functionalization of both possible lactam/lactim tautomers, through cycloaddition, to nucleophilic addition and transformation of the tautomeric C=O/C-OH moiety. The high availability of 2-pyridones and the possibility of their far-reaching functionalization additionally increased their values. Therefore, they are very useful building blocks for the synthesis of structurally diverse piperidine and pyridine compounds, including naturally occurring 2-pyridones. This review reports on the use of simple 2-pyridones in the synthesis of alkaloids and alkaloids-inspired compounds based on the piperidine or pyridine framework.

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