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.

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.;Frongia A.
2021-01-01

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.
2021
Carbocycles; Nitrogen heterocycles; Synthetic methods; Tandem reaction; α-iminol rearrangement
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11584/307100
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