title: Cyclobutene ring-opening of bicyclo[4.2.0]octa-1,6-dienes: access to CF3-substituted 5,6,7,8-tetrahydro-1,7-naphthyridines.
abstract: 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.
authors.affiliation: A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, 119991, Moscow, Russia.
authors.forename: Artur K
authors.initials: AK
authors.lastname: Mailyan
authors.forename: Alexander S
authors.initials: AS
authors.lastname: Peregudov
authors.forename: Pierre H
authors.initials: PH
authors.lastname: Dixneuf
authors.forename: Christian
authors.initials: C
authors.lastname: Bruneau
authors.forename: Sergey N
authors.initials: SN
authors.lastname: Osipov
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003503:Cyclobutanes / Q000737:chemistry*; D003516:Cycloparaffins / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D009287:Naphthyridines / Q000138:chemical synthesis
chemical_list: D001643:Bridged Bicyclo Compounds; D003503:Cyclobutanes; D003516:Cycloparaffins; D007659:Ketones; D009287:Naphthyridines