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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...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2023
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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. |
format | Online Article Text |
id | pubmed-10140734 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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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