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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Detalles Bibliográficos
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
Materias:
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
Descripción
Sumario: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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