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Organocatalysed one-pot three component synthesis of 3,3′-disubstituted oxindoles featuring an all-carbon quaternary center and spiro[2H-pyran-3,4′-indoline]

A simple and efficient methodology for the one-pot synthesis of 3,3′-disubstituted oxindoles featuring an all-carbon quaternary center has been demonstrated through l-proline catalysed three-component reaction based on sequential Knoevenagel condensation/Michael addition and also one-pot synthesis o...

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Detalles Bibliográficos
Autores principales: Nichinde, Chandrakant B., Patil, Baliram R., Chaudhari, Suryakant S., Mali, Bhupendra P., Gonnade, Rajesh G., Kinage, Anil K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10140734/
https://www.ncbi.nlm.nih.gov/pubmed/37123998
http://dx.doi.org/10.1039/d3ra00510k
Descripción
Sumario:A simple and efficient methodology for the one-pot synthesis of 3,3′-disubstituted oxindoles featuring an all-carbon quaternary center has been demonstrated through l-proline catalysed three-component reaction based on sequential Knoevenagel condensation/Michael addition and also one-pot synthesis of spiro[2H-pyran-3,4′-indoline] through consecutive Knoevenagel condensation/Michael addition/reduction/cyclization reactions from readily available isatin derivatives, malononitrile, and ketones. The present methodology presents several advantages, including simple reaction set-up, short reaction times, and easy to work-up. Also, this strategy offers broad substrate scope with excellent yields and high atom economy, under mild reaction conditions.