Easily accessible isoxazol-5(4H)-ones are useful precursors of heterocycles. In this context, we report the ruthenium-catalyzed transformation of 4-alkenyl-substituted isoxazol-5-ones to afford 1H-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.
Ruthenium-Catalyzed Decarboxylative Rearrangement of 4-Alkenyl-isoxazol-5-ones to Pyrrole Derivatives / L. Molteni, C. Loro, M. Christodoulou, M. Papis, F. Foschi, E. Beccalli, G. Broggini. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2022:25(2022 Jul 07), pp. e202200496.1-e202200496.5. [10.1002/ejoc.202200496]
Ruthenium-Catalyzed Decarboxylative Rearrangement of 4-Alkenyl-isoxazol-5-ones to Pyrrole Derivatives
L. Molteni;M. Christodoulou;E. Beccalli
Penultimo
;
2022
Abstract
Easily accessible isoxazol-5(4H)-ones are useful precursors of heterocycles. In this context, we report the ruthenium-catalyzed transformation of 4-alkenyl-substituted isoxazol-5-ones to afford 1H-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.File | Dimensione | Formato | |
---|---|---|---|
Eur J Org Chem - 2022 - Molteni - Ruthenium‐Catalyzed Decarboxylative Rearrangement of 4‐Alkenyl‐isoxazol‐5‐ones to Pyrrole.pdf
accesso aperto
Tipologia:
Publisher's version/PDF
Dimensione
4.36 MB
Formato
Adobe PDF
|
4.36 MB | Adobe PDF | Visualizza/Apri |
Pubblicazioni consigliate
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.