An Investigation into Domino‐Heck Reactions of N‐Acylamino‐Substituted Tricyclic Imides: Synthesis of New Prospective Pharmaceuticals |
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| Authors: | Emine Bagdatli Nüket Öcal Dieter E. Kaufmann |
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| Affiliation: | 1. Yildiz Technical University, Faculty of Art and Sciences, Department of Chemistry, Davutpasa Campus, TR‐34210 Istanbul (phone: +90(212)4491750);2. Clausthal University of Technology, Institute of Organic Chemistry, Leibnizstr. 6, D‐38678 Clausthal‐Zellerfeld |
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| Abstract: | Heck and domino‐Heck reactions of unsaturated N‐acylamino‐substituted tricyclic imides with aryl(heteroaryl) iodides and phenyl‐ or (trimethylsilyl)acetylene were either carried out in the presence of formate or phenyl‐ and (trimethylsilyl)acetylene, respectively. The C? C coupling reactions appeared to be completely diastereoselective, giving the corresponding N‐acylamino‐5‐exo‐aryl (heteroaryl)‐ ( 5a – c, 6a , b ), N‐(benzoylamino)‐5‐exo‐phenyl‐6‐exo‐[(trimethylsilyl)ethynyl]‐ ( 5d ), or 5‐exo‐(4‐chlorophenyl)‐N‐(2,2‐dimethylpropanoylamino)‐6‐exo‐(phenylethynyl)bicyclo[2.2.1]heptane‐2‐endo,3‐endo‐dicarboximide ( 6c ) (Schemes 3 and 4). |
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| Keywords: | Hydroarylation Imides, tricyclic Heterocycles Heck reactions Palladium catalysis Catalysis |
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