Traceless Redox-Annulations of Alicyclic Amines

Dillon R. L. Rickertsen; Longle Ma; Anirudra Paul; Khalil A. Abboud; Daniel Seidel

doi:10.1055/s-0040-1706004

SynOpen, Table of Contents

CC BY-NC-ND 4.0 · SynOpen 2020; 04(04): 123-131
DOI: 10.1055/s-0040-1706004

paper

Traceless Redox-Annulations of Alicyclic Amines

Dillon R. L. Rickertsen‡

^aCenter for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, USA

,

Longle Ma ‡

^bDepartment of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, USA

,

Anirudra Paul

^aCenter for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, USA

,

Khalil A. Abboud

^cCenter for X-ray Crystallography, Department of Chemistry, University of Florida, Gainesville, Florida 32611, USA

,

Daniel Seidel ∗

^aCenter for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, USA

› Author Affiliations

Abstract

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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.

Key words

C–H bond functionalization - redox-neutral - redox-annulation - denitration - decarboxylative annulation

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References

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