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

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 alpha-iminol rearrangement, ring expansion, ring closure, and a depart-and-return...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 53; no. 4; pp. 673 - 681
Main Authors Serusi, Lorenzo, Cuccu, Federico, Secci, Francesco, Aitken, David J., Frongia, Angelo
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 16.02.2021
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
tandem reaction
carbocycles
CYCLOBUTANE DERIVATIVES
alpha-iminol rearrangement
ALDOL REACTION
nitrogen heterocycles
HEYNS REARRANGEMENT
AMADORI
AMINO KETONE REARRANGEMENTS
synthetic methods
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Summary: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 alpha-iminol rearrangement, ring expansion, ring closure, and a depart-and-return rearrangement process.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0040-1706587