Issue 16, 2018

Oxidation of active sp3 C–H bonds initiated consecutive intermolecular/intramolecular cyclization between glycine derivatives and o-vinylphenols: construction of a polycyclic benzofuroquinoline skeleton

Abstract

Consecutive intermolecular/intramolecular cyclization between N-arylglycine derivatives and 2-hydroxylstyrenes was realized through radical cation salt-initiated sp3 C–H bond oxidation. This reaction provided a new route to forge this biologically important polycyclic benzofuroquinoline skeleton in a single synthetic step with good functional group tolerance. The mechanistic study revealed that the oxidation of the active sp3 C–H bond initiated further functionalization of the inert C–H bond and tandem cyclization.

Graphical abstract: Oxidation of active sp3 C–H bonds initiated consecutive intermolecular/intramolecular cyclization between glycine derivatives and o-vinylphenols: construction of a polycyclic benzofuroquinoline skeleton

Supplementary files

Article information

Article type
Research Article
Submitted
02 May 2018
Accepted
28 Jun 2018
First published
05 Jul 2018

Org. Chem. Front., 2018,5, 2479-2483

Oxidation of active sp3 C–H bonds initiated consecutive intermolecular/intramolecular cyclization between glycine derivatives and o-vinylphenols: construction of a polycyclic benzofuroquinoline skeleton

X. Jia, W. Hou, Q. Chen, Y. Yuan, J. Sun and K. He, Org. Chem. Front., 2018, 5, 2479 DOI: 10.1039/C8QO00444G

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