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2H-Azirines as C–C Annulation Reagents in Cu-Catalyzed Synthesis of Furo[3,2-c]quinolone Derivatives
- Sakharov, Pavel A., Rostovskii, Nikolai V., Khlebnikov, Alexander F., Panikorovskii, Taras L., Novikov, Mikhail S.
- Organic letters 2019 v.21 no.10 pp. 3615-3619
- azirines, carbamates, carbon, catalytic activity, chemical reactions, chemical structure, copper, nitrogen, quinolones
- A method of furo-annulation of 4-hydroxy-2-oxoquinoline-3-carboxylates with 3-arylazirines under Cu(II) catalysis was developed to synthesize a variety of 2,3-dihydrofuro[3,2-c]quinolones bearing a carbamate group at the C2 position. The reaction involves an azirine ring opening across the N–C2 bond and formation of a dihydrofuran ring with the inclusion of two azirine carbon atoms, accompanied by a shift of the ester group to the nitrogen. The discovered reaction is the first example of the use of 2H-azirines for furo-annulation.