Boger pyridine synthesis: Difference between revisions
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Revision as of 16:08, 30 October 2015
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The Boger pyridine synthesis is a cycloaddition approach to the formation of pyridines in which an enamine reacts in an inverse-electron demand Diels-Alder reaction with a 1,2,4-triazine to form the pyridine nucleus. The reaction is especially useful for accessing pyridines that would be difficult or impossible to access via other methods.
Mechanism
The enamine is generally generated in situ from catalytic amine (such as pyrrolidine) and a ketone. The enamine then reacts as the dienophile with a 1,2,4-triazine. The initial adduct then expels nitrogen, and the pyridine is rearomatized with loss of the amine.
References
- Boger, D.; Panek, J.; Meier, M. (1982). "Diels-Alder reaction of heterocyclic azadienes". J. Org. Chem. 47: 895.
- Li, Jie Jack (2002). Name Reactions A Collection of Detailed Reaction Mechanisms. Berlin: Springer-Verlag. p. 40. ISBN 3-540-43024-5.