Also known as: Pictet-Spengler tetrahydroisoquinoline synthesis
The Pictet-Spengler reaction is an organic reaction used to convert a β-arylenylamine and an aldehyde or ketone to a tetrahydroisoquinoline using an acid catalyst. The mechanism begins with protonation of the carbonyl oxygen by the acid which is subsequently attacked by the amine reagent. BuyVanadium(IV)bis(acetylacetonato)oxide 261768-25-6 Purity Proton transfer steps and the release of a water molecule results in a protonated imine intermediate, which then undergoes a 6-endo-trig cyclization reaction with loss of aromaticity of the aryl ring. A final deprotonation step restores the aromaticity and results in the tetrahydroisoquinoline product. [1]
Mechanism
References:
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Pictet, A.; Spengler, T. Ber. Dtsch. Chem. Ges. 1911, 44, 2030–2036.
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