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. 2016 Mar 4;18(5):1024-7.
doi: 10.1021/acs.orglett.6b00151. Epub 2016 Feb 19.

Redox-Annulation of Cyclic Amines and β-Ketoaldehydes

Weijie Chen  1 , Daniel Seidel  1
Affiliations

Redox-Annulation of Cyclic Amines and β-Ketoaldehydes

Weijie Chen et al. Org Lett. .

Abstract

Benzo[a]quinolizine-2-one derivatives are readily assembled from 1,2,3,4-tetrahydroisoquinoline and β-ketoaldehydes by means of a new intramolecular redox-Mannich process. These reactions are promoted by simple acetic acid and are thought to involve azomethine ylides as reactive intermediates.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Selected bioactive compounds containing the benzo[a]quinolizine and related structural motifs.
Scheme 1
Scheme 1. Scope of the Intramolecular Redox-Mannich Reaction with Non-enolizable β-Ketoaldehydes
Reactions were performed on a 0.5 mmol scale. All yields correspond to isolated yields of purified products.
Scheme 2
Scheme 2. Scope of the Intramolecular Redox-Mannich Reaction with Enolizable β-Ketoaldehydes
Reactions were performed on a 0.5 mmol scale. A solution of the aldehyde in 0.75 mL of toluene was added slowly over 15 h to a mixture of the amine, acetic acid, and 4 Å MS in 2 mL of toluene. All yields correspond to isolated yields of purified products. All reagents were mixed directly and heated under reflux in toluene (0.25 M) for 20 h.
See this image and copyright information in PMC

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