Synthesis of Benzo[c][2,7]naphthyridinones and Benzo[c][2,6]naphthyridinones via Ruthenium-Catalyzed [2+2+2] Cycloaddition between 1,7-Diynes and Cyanamides

A convenient method for the ruthenium-catalyzed synthesis of benzo­[c]­naphthyridinone derivatives is reported. The [2+2+2] cycloaddition from various mono- and disubstituted 1,7-diynes and cyanamides provided benzo­[c]­[2,7]­naphthyridinones as major products and benzo­[c]­[2,6]­naphthyridinones as...

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Published in:Organic letters 2022-07, Vol.24 (28), p.5126-5131
Main Authors: Huvelle, Steve, Matton, Pascal, Tran, Christine, Rager, Marie-Noelle, Haddad, Mansour, Ratovelomanana-Vidal, Virginie
Format: Article
Language:English
Subjects:
Chemical Sciences
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Summary:A convenient method for the ruthenium-catalyzed synthesis of benzo­[c]­naphthyridinone derivatives is reported. The [2+2+2] cycloaddition from various mono- and disubstituted 1,7-diynes and cyanamides provided benzo­[c]­[2,7]­naphthyridinones as major products and benzo­[c]­[2,6]­naphthyridinones as minor ones in yields of ≤79% and regioselectivities of ≤99:1. This method is amenable to internal and terminal diynes and a number of cyanamides with diverse functional group tolerance.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01963