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. 2020;4(4):123-131.
doi: 10.1055/s-0040-1706004. Epub 2020 Dec 16.

Traceless Redox-Annulations of Alicyclic Amines

Dillon R L Rickertsen  1 , Longle Ma  2 , Anirudra Paul  1 , Khalil A Abboud  3 , Daniel Seidel  1
Affiliations

Traceless Redox-Annulations of Alicyclic Amines

Dillon R L Rickertsen et al. SynOpen. 2020.

Abstract

Amines such as 1,2,3,4-tetrahydroisoquinoline undergo redox-neutral annulations with ortho-(nitromethyl)benzaldehyde. Benzoic acid acts as a promoter in these reactions, which involve concurrent amine α-C-H bond and N-H bond functionalization. Subsequent removal of the nitro group provides access to tetrahydroprotoberberines not accessible via typical redox-annulations. Also reported are decarboxylative annulations of ortho-(nitromethyl)benzaldehyde with proline and pipecolic acid.

Keywords: C–H bond functionalization; decarboxylative annulation; denitration; redox-annulation; redox-neutral.

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Figures

Scheme 1
Scheme 1
Examples of amine redox-annulations and present work
Scheme 2
Scheme 2
Equilibration experiment
Scheme 3
Scheme 3
Evaluation of substituted tetrahydroisoquinolines
Scheme 4
Scheme 4
Formation of sterically congested tetrahydroprotoberberine analogues
Scheme 5
Scheme 5
Denitration of a sterically congested annulation product
Scheme 6
Scheme 6
Decarboxylative annulation/denitration
See this image and copyright information in PMC

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