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

Molecules

Abdulrahman I. Almansour¹  Natarajan Arumugam¹  Raju Suresh Kumar¹  Govindasami Periyasami³  Hazem A. Ghabbour²  Hoong-Kun Fun² 

[1] Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia;Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia;Centro de Química-Física Molecular and Institute of Nanoscience and Nanotechnology, Instituto Superior Técnico, Universidade de Lisboa, Lisboa 1049-001, Portugal

关键词: 1;    3-dipolar cycloaddition;    azomethine ylide;    dispiropyrrolidines;    ionic liquids;   

DOI  :  10.3390/molecules20010780

来源: mdpi

【 摘 要 】

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]BF₄, furnished the cycloadducts in good yields, with the regioisomers 5a–f being obtained with high selectivity. Furthermore, the recyclability of [bmim]BF₄, up to five times, was also investigated.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.