4-Quinolones are the structural elements of many pharmaceutically active compounds. Although several approaches are known for their synthesis, the introduction of an aryl ring in position 2 is problematic with most of them. The reductive cyclization of o-nitrochalcones by pressurized CO, catalyzed by ruthenium or palladium complexes, has been previously reported to be a viable synthetic strategy for this aim, but the need for pressurized CO lines and autoclaves has prevented its widespread use. In this paper, we describe the use of the formic acid/acetic anhydride mixture as a CO surrogate, which allows us to perform the reaction in a cheap and commercially available thick-walled glass tube without adding any gaseous reagent. The obtained yields are often high and compare favorably with those previously reported by the use of pressurized CO. The procedure was applied to a three-step synthesis from commercially available and cheap reagents of the alkaloid Graveoline.

Effective Synthesis of 4-Quinolones by Reductive Cyclization of 2′-Nitrochalcones Using Formic Acid as a CO Surrogate / F.M. Ferretti, M.A.F. Abdellatif, C. Abbo, F. Ragaini. - In: MOLECULES. - ISSN 1420-3049. - 28:14(2023), pp. 5424.1-5424.14. [10.3390/molecules28145424]

Effective Synthesis of 4-Quinolones by Reductive Cyclization of 2′-Nitrochalcones Using Formic Acid as a CO Surrogate

F.M. Ferretti
Primo
;
M.A.F. Abdellatif
Secondo
;
F. Ragaini
Ultimo
2023

Abstract

4-Quinolones are the structural elements of many pharmaceutically active compounds. Although several approaches are known for their synthesis, the introduction of an aryl ring in position 2 is problematic with most of them. The reductive cyclization of o-nitrochalcones by pressurized CO, catalyzed by ruthenium or palladium complexes, has been previously reported to be a viable synthetic strategy for this aim, but the need for pressurized CO lines and autoclaves has prevented its widespread use. In this paper, we describe the use of the formic acid/acetic anhydride mixture as a CO surrogate, which allows us to perform the reaction in a cheap and commercially available thick-walled glass tube without adding any gaseous reagent. The obtained yields are often high and compare favorably with those previously reported by the use of pressurized CO. The procedure was applied to a three-step synthesis from commercially available and cheap reagents of the alkaloid Graveoline.
carbonylation; chalcones; CO surrogate; homogeneos catalysis; N-heterocycles; nitroarenes; palladium; quinolones
Settore CHIM/03 - Chimica Generale e Inorganica
Settore CHIM/06 - Chimica Organica
2023
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/993592
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