Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2007(4): 0364-0364
DOI: 10.1055/s-2007-968380
DOI: 10.1055/s-2007-968380
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Radical Cyclization of N-Acylcyanamides to Pyrroloquinazolines
A. Servais, M. Azzouz, D. Lopes, C. Courillon*, M. Malacria*
UniversitÉ Pierre et Marie Curie, Paris, France
Further Information
Publication History
Publication Date:
23 March 2007 (online)
![](https://www.thieme-connect.de/media/synfacts/200704/lookinside/thumbnails/10.1055-s-2007-968380-1.jpg)
Significance
N-Acyl-N-cyanamides, readily prepared by two convenient methods, undergo radical-induced cyclization to afford polycyclic pyrroloquinazolines in good to excellent yields. The proposed mechanism is a radical cascade reaction in which a 5-exo-dig cyclization process of the initial aryl radical leads to the cyanamide. The resulting radical is captured by an enone or an aromatic double bond to give the product. In the absence of unsaturated bonds, for example R1, R2 = Me, fragmentation occurs forming an ortho-cyano benzylamide.