Traceless Redox-Annulations of Alicyclic Amines.

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.

SUBMITTER: Rickertsen DRL 

PROVIDER: S-EPMC8318209 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature