Alkene carboamination/oxidative denitrogenation of 3-allyl-3-hydrazinylindolin-2-ones: one-pot entry to spirocyclopropyloxindoles
Articolo
Data di Pubblicazione:
2024
Citazione:
Alkene carboamination/oxidative denitrogenation of 3-allyl-3-hydrazinylindolin-2-ones: one-pot entry to spirocyclopropyloxindoles / M. Manenti, T. Villa, G. Macetti, A. Silvani. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - (2024), pp. 1-13. [Epub ahead of print] [10.1039/D3OB02115G]
Abstract:
A one-pot protocol, consisting of a Pd-catalysed carboamination reaction, followed by N-deprotection and oxidative denitrogenation, has been developed for the synthesis of diversely substituted spirocyclopropyloxindoles, in yields up to 73% and with diastereoselectivity close to 1 : 1. Readily accessible starting materials, mild reaction conditions, an easy to operate one-pot procedure and good functional group tolerance make this transformation a versatile tool for the synthesis of substituted spirocyclopropyloxindoles. This protocol successfully works on the gram-scale and allows access to both diastereoisomers separately. A plausible mechanism was proposed, and a series of post-transformations were performed on the obtained products, showing their remarkable synthetic versatility.
Tipologia IRIS:
01 - Articolo su periodico
Elenco autori:
M. Manenti, T. Villa, G. Macetti, A. Silvani
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