Bobbitt reaction

[1] The reaction allows the synthesis of 1-, 4-, and N-substituted 1,2,3,4-tetrahydroisoquinolines and also 1-, and 4-substituted isoquinolines.

The reaction scheme below shows the synthesis of 1,2,3,4-tetrahydroisoquinoline from benzaldehyde and 2,2-diethylethylamine.

[1] A possible mechanism is depicted below:[1] First the benzaliminoacetal 3 is built by the condensation of benzaldehyde 1 and 2,2-diethylethylamine 2.

Next, the compound 5 is built including the cyclization step.

The Bobbitt reaction has found application in the preparation of some alkaloids[1] such as carnegine,[2] lophocerine, salsolidine,[2] and salsoline.