jo301501r_si_001.cif (16.2 kB)

Cyclobutene Ring-Opening of Bicyclo[4.2.0]octa-1,6-dienes: Access to CF3‑Substituted 5,6,7,8-Tetrahydro-1,7-naphthyridines

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posted on 05.10.2012, 00:00 by Artur K. Mailyan, Alexander S. Peregudov, Pierre H. Dixneuf, Christian Bruneau, Sergey N. Osipov
An efficient method for the synthesis of novel CF3-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.