Divergent Sequential Reactions of β‐(2‐Aminophenyl)‐α, β‐ynones with Malonyl Chloride. Issue 45 (1st December 2022)

• Record Type: Journal Article
• Authors: Marsicano, Vincenzo; Marraffa, Gianpaolo; Chiarini, Marco; Palombi, Laura; Arcadi, Antonio
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 45(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-12-01
• Subjects: Annulation reactions -- Product selectivity -- Sequential reactions -- Synthetic methods -- Polycyclic derivatives; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202201187
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A viable one‐pot synthesis of challenging 4H ‐[3, 4‐ c ]quinolone‐4, 5( 6H )‐diones by the reaction of β‐(2‐aminophenyl)‐α, β‐ynones with ethyl malonyl chloride is described. Their further elaboration in the presence of an excess of 40 % methyl amine aqueous solution in EtOH gives the benzo[ c ][2, 7]naphthyridine‐4, 5( 3H, 6H )‐diones of pharmacological interest in high yields. The product selectivity control of the divergent sequential condensation/ C‐annulation/ intramolecular transesterification vs condensation/ O‐annulation/ ring opening reactions of β‐(2‐aminophenyl)‐α, β‐ynones with malonyl chloride under metal free conditions has been addressed. Abstract : The investigation on the product selectivity control of divergent domino reactions of β‐(2‐aminophenyl)‐α, β‐ynones with acyl chlorides is reported. A viable approach to the synthesis of challenging 4H ‐[3, 4‐ c ]quinolone‐4, 5( 6H )‐diones and benzo[ c ][2, 7]naphthyridine‐4, 5( 3H, 6H )‐diones is described.