Photochemical aryl radical cyclizations to give (E)-3-ylideneoxindoles

Michael Gurry; Ingrid Allart-Simon; Patrick McArdle; Stéphane Gérard; Janos Sapi; Fawaz Aldabbagh

doi:10.3390/molecules191015891

Photochemical aryl radical cyclizations to give (E)-3-ylideneoxindoles

Molecules. 2014 Sep 30;19(10):15891-9. doi: 10.3390/molecules191015891.

Authors

Michael Gurry¹, Ingrid Allart-Simon², Patrick McArdle¹, Stéphane Gérard², Janos Sapi², Fawaz Aldabbagh³

Affiliations

¹ School of Chemistry, National University of Ireland Galway, University Road, Galway, Ireland.
² Institut de Chimie Moléculaire de Reims, UMR CNRS 7312, Université de Reims-Champagne-Ardenne, Faculté de Pharmacie, 51 rue Cognacq-Jay, F-51096 Reims Cedex, France.
³ School of Chemistry, National University of Ireland Galway, University Road, Galway, Ireland. [email protected].

Abstract

(E)-3-Ylideneoxindoles are prepared in methanol in reasonable to good yields, as adducts of photochemical 5-exo-trig of aryl radicals, in contrast to previously reported analogous radical cyclizations initiated by tris(trimethylsilyl)silane and azo-initiators that gave reduced oxindole adducts.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cyclization
Free Radicals / chemical synthesis
Free Radicals / chemistry*
Models, Molecular
Molecular Structure
Oxidants, Photochemical / chemical synthesis
Oxidants, Photochemical / chemistry*

Substances

Free Radicals
Oxidants, Photochemical