TheBoger pyridine synthesis is acycloaddition approach to the formation ofpyridines named after its inventorDale L. Boger, who first reported it in 1981.[1] The reaction is a form ofinverse-electron demand Diels-Alder reaction in which anenamine reacts with a 1,2,4-triazine to form the pyridine nucleus.[2][3] The reaction is especially useful for accessing pyridines that would be difficult or impossible to access via other methods and has been used in thetotal synthesis of several complicated natural products.[4]
The enamine is generally generatedin 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.
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