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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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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
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author Nichinde, Chandrakant B.
Patil, Baliram R.
Chaudhari, Suryakant S.
Mali, Bhupendra P.
Gonnade, Rajesh G.
Kinage, Anil K.
author_facet Nichinde, Chandrakant B.
Patil, Baliram R.
Chaudhari, Suryakant S.
Mali, Bhupendra P.
Gonnade, Rajesh G.
Kinage, Anil K.
author_sort Nichinde, Chandrakant B.
collection PubMed
description 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.
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spelling pubmed-101407342023-04-29 Organocatalysed one-pot three component synthesis of 3,3′-disubstituted oxindoles featuring an all-carbon quaternary center and spiro[2H-pyran-3,4′-indoline] Nichinde, Chandrakant B. Patil, Baliram R. Chaudhari, Suryakant S. Mali, Bhupendra P. Gonnade, Rajesh G. Kinage, Anil K. RSC Adv Chemistry 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. The Royal Society of Chemistry 2023-04-28 /pmc/articles/PMC10140734/ /pubmed/37123998 http://dx.doi.org/10.1039/d3ra00510k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Nichinde, Chandrakant B.
Patil, Baliram R.
Chaudhari, Suryakant S.
Mali, Bhupendra P.
Gonnade, Rajesh G.
Kinage, Anil K.
Organocatalysed one-pot three component synthesis of 3,3′-disubstituted oxindoles featuring an all-carbon quaternary center and spiro[2H-pyran-3,4′-indoline]
title Organocatalysed one-pot three component synthesis of 3,3′-disubstituted oxindoles featuring an all-carbon quaternary center and spiro[2H-pyran-3,4′-indoline]
title_full Organocatalysed one-pot three component synthesis of 3,3′-disubstituted oxindoles featuring an all-carbon quaternary center and spiro[2H-pyran-3,4′-indoline]
title_fullStr Organocatalysed one-pot three component synthesis of 3,3′-disubstituted oxindoles featuring an all-carbon quaternary center and spiro[2H-pyran-3,4′-indoline]
title_full_unstemmed Organocatalysed one-pot three component synthesis of 3,3′-disubstituted oxindoles featuring an all-carbon quaternary center and spiro[2H-pyran-3,4′-indoline]
title_short Organocatalysed one-pot three component synthesis of 3,3′-disubstituted oxindoles featuring an all-carbon quaternary center and spiro[2H-pyran-3,4′-indoline]
title_sort organocatalysed one-pot three component synthesis of 3,3′-disubstituted oxindoles featuring an all-carbon quaternary center and spiro[2h-pyran-3,4′-indoline]
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10140734/
https://www.ncbi.nlm.nih.gov/pubmed/37123998
http://dx.doi.org/10.1039/d3ra00510k
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