Ruthenium‐Catalyzed Decarboxylative Rearrangement of 4‐Alkenyl‐isoxazol‐5‐ones to Pyrrole Derivatives. Issue 25 (1st July 2022)

• Record Type: Journal Article
• Authors: Molteni, Letizia; Loro, Camilla; Christodoulou, Michael S.; Papis, Marta; Foschi, Francesca; Beccalli, Egle M.; Broggini, Gianluigi
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 25(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-07-01
• Subjects: Decarboxylation -- Nitrogen heterocycles -- Pyrroles -- Rearrangement -- Ruthenium; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202200496
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Easily accessible isoxazol‐5(4 H )‐ones are useful precursors of heterocycles. In this context, we report the ruthenium‐catalyzed transformation of 4‐alkenyl‐substituted isoxazol‐5‐ones to afford 1 H ‐pyrrole derivatives. The operative conditions were proven to be effective also on cyclohexane‐fused isoxazolones giving 4, 5, 6, 7‐tetrahydroindoles. The reactions, which allow for access to tri‐and tetra‐substituted pyrroles in moderate to high yields, occur through decarboxylative ring‐opening/ring‐closure involving C−H functionalization of the alkenyl moiety. Abstract : Easily accessible isoxazol‐5(4 H )‐ones are useful precursors of different heterocycles. In this work, the ruthenium‐catalyzed transformation of 4‐alkenyl‐substituted isoxazol‐5‐ones to 1 H ‐pyrrole derivatives is reported.