Traceless Redox-Annulations of Alicyclic Amines

SynOpen

Dillon R. L. Rickertsen¹  Daniel Seidel¹  Anirudra Paul¹  Khalil A. Abboud²  Longle Ma³ 

[1] Center for Heterocyclic Compounds, Department of Chemistry, University of Florida;Center for X-ray Crystallography, Department of Chemistry, University of Florida;Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey;

关键词: c–h bond functionalization;    redox-neutral;    redox-annulation;    denitration;    decarboxylative annulation;   

DOI  :  10.1055/s-0040-1706004

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown