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

Lorenzo Serusi; Federico Cuccu; Francesco Secci; David J. Aitken; Angelo Frongia

doi:10.1055/s-0040-1706587

Synthesis, Table of Contents

Synthesis 2021; 53(04): 673-681
DOI: 10.1055/s-0040-1706587

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

Authors

Lorenzo Serusi

^aDipartimento di Scienze Chimiche e Geologiche, Università degli Studi di Cagliari, Complesso Universitario di Monserrato, S.S. 554, Bivio per Sestu, 09042, Monserrato, Cagliari, Italy Email: afrongia@unica.it
Federico Cuccu

^aDipartimento di Scienze Chimiche e Geologiche, Università degli Studi di Cagliari, Complesso Universitario di Monserrato, S.S. 554, Bivio per Sestu, 09042, Monserrato, Cagliari, Italy Email: afrongia@unica.it
Francesco Secci

^aDipartimento di Scienze Chimiche e Geologiche, Università degli Studi di Cagliari, Complesso Universitario di Monserrato, S.S. 554, Bivio per Sestu, 09042, Monserrato, Cagliari, Italy Email: afrongia@unica.it
David J. Aitken

^bICMMO, CP3A Organic Synthesis Group, Université Paris Saclay, CNRS, Bât 420, rue du Doyen Georges Poitou, 91405 Orsay cedex, France
Angelo Frongia ∗

^aDipartimento di Scienze Chimiche e Geologiche, Università degli Studi di Cagliari, Complesso Universitario di Monserrato, S.S. 554, Bivio per Sestu, 09042, Monserrato, Cagliari, Italy Email: afrongia@unica.it

Abstract

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Abstract

A novel Brønsted 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.

Key words

tandem reaction - carbocycles - nitrogen heterocycles - synthetic methods - α-iminol rearrangement

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References

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Supplementary Material

Supporting Information (PDF)