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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• 作者：Artur K. Mailyan ; Alexander S. Peregudov ; Pierre H. Dixneuf ; Christian Bruneau ; Sergey N. Osipov
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：October 5, 2012
• 年：2012
• 卷：77
• 期：19
• 页码：8518-8526
• 全文大小：334K
• 年卷期：v.77,no.19(October 5, 2012)
• ISSN：1520-6904

文摘

An efficient method for the synthesis of novel CF₃-substituted tetrahydro-1,7-naphthyridines including cyclic 伪-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.