Traceless Redox-Annulations of Alicyclic Amines.

Dillon R L RickertsenLongle MaAnirudra PaulKhalil A AbboudDaniel Seidel

Published in: SynOpen (2017) (2020)

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.

Keyphrases

electron transfer
dna methylation
gene expression
locally advanced
radiation therapy
transition metal
rectal cancer