通过甲亚胺叶立德的1,3-偶极环加成反应一锅法绿色合成双螺氧化吲哚-吡咯烷类化合物。

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

作者信息

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

机构信息

Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, 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.

出版信息

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

DOI:10.3390/molecules20010780

PMID:25574820

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6272743/

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.

摘要

通过一锅三组分1,3 - 偶极环加成反应实现了双螺氧化吲哚吡咯烷的简便合成。由L - 苯丙氨酸和取代靛红原位生成的甲亚胺叶立德与一系列不同寻常的（E）-2 - 氧代吲哚啉 - 3 - 亚基苯乙酮亲偶极体在离子液体1 - 丁基 - 3 - 甲基咪唑溴盐[bmim]BF4中反应，以良好的产率得到环加成产物，区域异构体5a - f具有高选择性。此外，还研究了[bmim]BF4高达五次的可循环性。