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Metal-free oxidative functionalization of a C(sp(3))-H bond adjacent to nitrogen and intramolecular aromatic cyclization for the preparation of 6-amidophenanthridines.

Authors
  • Fang, Hong
  • Zhao, Jincan
  • Ni, Shengyang
  • Mei, Haibo
  • Han, Jianlin
  • Pan, Yi
Type
Published Article
Journal
The Journal of Organic Chemistry
Publisher
American Chemical Society
Publication Date
Mar 20, 2015
Volume
80
Issue
6
Pages
3151–3158
Identifiers
DOI: 10.1021/acs.joc.5b00058
PMID: 25742029
Source
Medline
License
Unknown

Abstract

A metal-free cyclization reaction of 2-isocyanobiphenyls with amide derivatives by using tert-butyl peroxybenzoate (TBPB) as oxidant was developed, which provided an access to pharmacologically interesting 6-amidophenanthridine compounds. The reactions proceeded through a sequence of functionalization of the C(sp(3))-H bond adjacent to the nitrogen atom and intramolecular radical aromatic cyclization with good chemistry yields.

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