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; Alexander S Peregudov; Pierre H Dixneuf; Christian Bruneau; Sergey N Osipov

doi:10.1021/jo301501r

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

J Org Chem. 2012 Oct 5;77(19):8518-26. doi: 10.1021/jo301501r. Epub 2012 Sep 14.

Authors

Artur K Mailyan¹, Alexander S Peregudov, Pierre H Dixneuf, Christian Bruneau, Sergey N Osipov

Affiliation

¹ A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, 119991, Moscow, Russia.

PMID: 22950872
DOI: 10.1021/jo301501r

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bridged Bicyclo Compounds / chemical synthesis*
Bridged Bicyclo Compounds / chemistry*
Catalysis
Cyclization
Cyclobutanes / chemistry*
Cycloparaffins / chemistry*
Ketones / chemistry*
Molecular Structure
Naphthyridines / chemical synthesis

Substances

Bridged Bicyclo Compounds
Cyclobutanes
Cycloparaffins
Ketones
Naphthyridines