A Novel One-Pot Green Synthesis of Dispirooxindolo-pyrrolidines via1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides

A facile synthesis of dispirooxindolopyrrolidines has been accomplished via a one-pot three component 1,3-dipolar cycloaddition reaction. The reaction of azomethine ylides generated in situ from L-phenylalanine and substituted isatins with a series of unusual (E)-2-oxoindolino-3-ylidene acetophenone...

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Autores principales: Almansour, Abdulrahman I., Arumugam, Natarajan, Kumar, Raju Suresh, Periyasami, Govindasami, Ghabbour, Hazem A., Fun, Hoong-Kun
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2015
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Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272743/
https://www.ncbi.nlm.nih.gov/pubmed/25574820
http://dx.doi.org/10.3390/molecules20010780
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author Almansour, Abdulrahman I.
Arumugam, Natarajan
Kumar, Raju Suresh
Periyasami, Govindasami
Ghabbour, Hazem A.
Fun, Hoong-Kun
author_facet Almansour, Abdulrahman I.
Arumugam, Natarajan
Kumar, Raju Suresh
Periyasami, Govindasami
Ghabbour, Hazem A.
Fun, Hoong-Kun
author_sort Almansour, Abdulrahman I.
collection PubMed
description A facile synthesis of dispirooxindolopyrrolidines has been accomplished via a one-pot three component 1,3-dipolar cycloaddition reaction. The reaction of azomethine ylides generated in situ from L-phenylalanine and substituted isatins with a series of unusual (E)-2-oxoindolino-3-ylidene acetophenone dipolarophiles in the ionic liquid 1-butyl-3-methylimidazolium bromide [bmim]BF(4), furnished the cycloadducts in good yields, with the regioisomers 5a–f being obtained with high selectivity. Furthermore, the recyclability of [bmim]BF(4), up to five times, was also investigated.
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spelling pubmed-62727432018-12-28 A Novel One-Pot Green Synthesis of Dispirooxindolo-pyrrolidines via1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides Almansour, Abdulrahman I. Arumugam, Natarajan Kumar, Raju Suresh Periyasami, Govindasami Ghabbour, Hazem A. Fun, Hoong-Kun Molecules Article A facile synthesis of dispirooxindolopyrrolidines has been accomplished via a one-pot three component 1,3-dipolar cycloaddition reaction. The reaction of azomethine ylides generated in situ from L-phenylalanine and substituted isatins with a series of unusual (E)-2-oxoindolino-3-ylidene acetophenone dipolarophiles in the ionic liquid 1-butyl-3-methylimidazolium bromide [bmim]BF(4), furnished the cycloadducts in good yields, with the regioisomers 5a–f being obtained with high selectivity. Furthermore, the recyclability of [bmim]BF(4), up to five times, was also investigated. MDPI 2015-01-07 /pmc/articles/PMC6272743/ /pubmed/25574820 http://dx.doi.org/10.3390/molecules20010780 Text en © 2015 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Almansour, Abdulrahman I.
Arumugam, Natarajan
Kumar, Raju Suresh
Periyasami, Govindasami
Ghabbour, Hazem A.
Fun, Hoong-Kun
A Novel One-Pot Green Synthesis of Dispirooxindolo-pyrrolidines via1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides
title A Novel One-Pot Green Synthesis of Dispirooxindolo-pyrrolidines via1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides
title_full A Novel One-Pot Green Synthesis of Dispirooxindolo-pyrrolidines via1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides
title_fullStr A Novel One-Pot Green Synthesis of Dispirooxindolo-pyrrolidines via1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides
title_full_unstemmed A Novel One-Pot Green Synthesis of Dispirooxindolo-pyrrolidines via1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides
title_short A Novel One-Pot Green Synthesis of Dispirooxindolo-pyrrolidines via1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides
title_sort novel one-pot green synthesis of dispirooxindolo-pyrrolidines via1,3-dipolar cycloaddition reactions of azomethine ylides
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272743/
https://www.ncbi.nlm.nih.gov/pubmed/25574820
http://dx.doi.org/10.3390/molecules20010780
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