A novel one-pot green synthesis of dispirooxindolo-pyrrolidines via 1,3-dipolar cycloaddition reactions of azomethine ylides

Abdulrahman I Almansour; Natarajan Arumugam; Raju Suresh Kumar; Govindasami Periyasami; Hazem A Ghabbour; Hoong-Kun Fun

doi:10.3390/molecules20010780

A novel one-pot green synthesis of dispirooxindolo-pyrrolidines via 1,3-dipolar cycloaddition reactions of azomethine ylides

Molecules. 2015 Jan 7;20(1):780-91. doi: 10.3390/molecules20010780.

Authors

Abdulrahman I Almansour¹, Natarajan Arumugam², Raju Suresh Kumar¹, Govindasami Periyasami³, Hazem A Ghabbour⁴, Hoong-Kun Fun⁴

Affiliations

¹ Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
² Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia. anatarajan@ksu.edu.sa.
³ Centro de Química-Física Molecular and Institute of Nanoscience and Nanotechnology, Instituto Superior Técnico, Universidade de Lisboa, Lisboa 1049-001, Portugal.
⁴ Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia.

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Azo Compounds / chemistry*
Crystallography, X-Ray
Cycloaddition Reaction*
Magnetic Resonance Spectroscopy
Models, Molecular
Pyrrolidines / chemical synthesis*
Spectrometry, Mass, Electrospray Ionization
Spectrophotometry, Infrared
Thiosemicarbazones / chemistry*

Substances

Azo Compounds
Pyrrolidines
Thiosemicarbazones
azomethine