Synthesis of Tryptamines through a Novel Bronsted Acid Mediated Tandem Reaction Initiated by α-Iminol Rearrangement of Transient 2-Substituted 2-Hydroxycyclobutylimines

Serusi L.;Cuccu F.;Secci F.;Aitken D. J.;Frongia A.

2021-01-01

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Abstract

A novel Bronsted acid promoted condensation reaction between a primary aniline and 2-hydroxycyclobutanone provides access to diverse tryptamine derivatives in moderate to good yields. The proposed mechanism involves an α-iminol rearrangement, ring expansion, ring closure, and a depart-And-return rearrangement process.