Remodeling of the Indole Ring with Redistribution of the C2 Atom: Switchable Access to Phenanthridines and Phenanthridine N-Oxides
Li Yang , Cheng Xu , Zheng Liu , Lijing Zhong , Qing Wang , Qian Shu , Shui Qian , Rongchuan Su , Guodong Yin , Ge Gao
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (21) : 2729 -2734.
Remodeling of the Indole Ring with Redistribution of the C2 Atom: Switchable Access to Phenanthridines and Phenanthridine N-Oxides
The skeletal remodeling of nitro-biphenyl indoles has been achieved via the cleavage of C2–N1 bond of and redistribution of the C2 atom. A diverse range of phenanthridines and phenanthridine N-oxides were switchably synthesized through fine-tuning the amount of HCl and reaction atmosphere. The scale-up synthesis and late-stage modification of the resulting products expand the application potential of this methodology. Furthermore, DFT calculations indicate that the ring-opening of indole necessitates the assistance of EtOH. This work establishes an attractive platform for the remodeling and conversion of N-heterocyclic frameworks.
Skeletal remodeling / Indoles / Phenanthridines / Switchable synthesis / Cyclization / Reduction / Nitrogen heterocycles / Cleavage reactions
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
/
| 〈 |
|
〉 |
PDF
