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 (Oct 2020)

Traceless Redox-Annulations of Alicyclic Amines

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

Affiliations

Dillon R. L. Rickertsen: Center for Heterocyclic Compounds, Department of Chemistry, University of Florida
Longle Ma: Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey
Anirudra Paul: Center for Heterocyclic Compounds, Department of Chemistry, University of Florida
Khalil A. Abboud: Center for X-ray Crystallography, Department of Chemistry, University of Florida
Daniel Seidel: Center for Heterocyclic Compounds, Department of Chemistry, University of Florida

DOI: https://doi.org/10.1055/s-0040-1706004
Journal volume & issue: Vol. 04, no. 04
pp. 123 – 131

Abstract

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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.

Published in SynOpen

ISSN: 2509-9396 (Online)
Publisher: Georg Thieme Verlag KG
Country of publisher: Germany
LCC subjects: Science: Chemistry
Website: https://doi.org/10.1055/s-00032269

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Abstract

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