Cyclobutene ring-opening of bicyclo[4.2.0]octa-1,6-dienes: access to CF3-substituted 5,6,7,8-tetrahydro-1,7-naphthyridines.

Artur K Mailyan (1) , Alexander S Peregudov (1) , Pierre H. Dixneuf (2) , Christian Bruneau (2) , Sergey N Osipov (1)

1 INEOS - A. N. Nesmeyanov Institute of Organoelement Compounds
2 ISCR - Institut des Sciences Chimiques de Rennes

An efficient method for the synthesis of novel CF(3)-substituted tetrahydro-1,7-naphthyridines including cyclic α-amino acid derivatives has been developed. The method is based on unusual cyclobutene ring-opening of bicyclo[4.2.0]octa-1,6-dienes with pyrrolidine to afford the corresponding 1,5-diketones followed by their heterocyclization. A convenient one-pot procedure has been also elaborated starting from readily available trifluoromethylated 1,6-allenynes.

Domaines: Catalyse

Artur K Mailyan, Alexander S Peregudov, Pierre H. Dixneuf, Christian Bruneau, Sergey N Osipov. Cyclobutene ring-opening of bicyclo[4.2.0]octa-1,6-dienes: access to CF3-substituted 5,6,7,8-tetrahydro-1,7-naphthyridines.. Journal of Organic Chemistry, 2012, 77 (19), pp.8518-26. ⟨10.1021/jo301501r⟩. ⟨hal-00805226⟩