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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 YorkRadical Cyclization of N-Acylcyanamides to Pyrroloquinazolines
A. Servais, M. Azzouz, D. Lopes, C. Courillon*, M. Malacria*
UniversitÉ Pierre et Marie Curie, Paris, France
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
23. März 2007 (online)

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.