We gratefully acknowledge financial support from MIUR (2006–2007 Funds for “Extending the Application of Organic Free Radicals to New Synthetic Methods”).
Approach to Spirocyclohexadienimines and Corresponding Dienones through Radical ipso Cyclization onto Aromatic Azides†
Article first published online: 29 OCT 2008
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 47, Issue 49, pages 9439–9442, November 24, 2008
How to Cite
Lanza, T., Leardini, R., Minozzi, M., Nanni, D., Spagnolo, P. and Zanardi, G. (2008), Approach to Spirocyclohexadienimines and Corresponding Dienones through Radical ipso Cyclization onto Aromatic Azides. Angew. Chem. Int. Ed., 47: 9439–9442. doi: 10.1002/anie.200804333
- Issue published online: 20 NOV 2008
- Article first published online: 29 OCT 2008
- Manuscript Received: 2 SEP 2008
- radical reactions;
- reactive intermediates;
- spiro compounds
Ipsoeasy: Cyclization of aryl radicals at the ipso-position of p-azido-substituted benzamides or 2-phenylacetamides results in effective production of spirocyclohexadieniminyl radicals through prompt elimination of molecular nitrogen by transient azidocyclohexadienyl radicals. The resultant iminyl radicals can be exploited for the synthesis of oxindoles or quinolones bearing spiro-cyclohexadienimine/cyclohexadienone rings (see picture, TTMSS=tris(trimethylsilyl)silane).