Intramolecular carbolithiation of N-allyl-ynamides: an efficient entry to 1,4-dihydropyridines and pyridines - application to a formal synthesis of sarizotan.
We have developed a general synthesis of polysubstituted 1,4-dihydropyridines and pyridines based on a highly regioselective lithiation/6-endo-dig intramolecular carbolithiation from readily available N-allyl-ynamides. This reaction, which has been successfully applied to the formal synthesis of the anti-dyskinesia agent sarizotan, further extends the use of ynamides in organic synthesis and further demonstrates the synthetic efficiency of carbometallation reactions.
Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles Saint-Quentin-en-Yvelines, 45, avenue des Etats-Unis, 78035 Versailles Cedex, France ; Laboratoire de Chimie Organique Hétérocyclique LCOH/LCOHSNR-LR11ES39, Département de Chimie, Faculté des Sciences de Monastir, Université de Monastir, avenue de l'environnement, 5019 Monastir, Tunisia.
Wafa
W
Gati
Mohamed M
MM
Rammah
Mohamed B
MB
Rammah
Gwilherm
G
Evano
carbolithiation; carbometallation; dihydropyridines; organolithium reagents; pyridines; sarizotan; ynamides