Sintesis sebatian isoxazolidina melalui tindakbalas 1,3-dwikutub pensiklotambahan N-4-tetra-benzilidina nitron dan maleimida dalam cecair ionik berasaskan imidazolium

Translated title of the contribution: Synthesis of isoxazolidine via 1,3-dipolar cycloaddition of N-4-tert-benzylidene nitrone and maleimide in imidazolium-based ionic liquids

Nur Liyana Sakinah Johari, Siti Nashwa Mohd Poad, Nur Hasyareeda Hassan, Nurul Izzaty Hassan

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The development of environmentally friendly methodologies for pericyclic reactions such as Diels Alder reaction is astonishing. Nevertheless, this is still scarce for the rest of pericyclic reactions. In this work, diastereosiomeric cycloadducts were formed via 1,3-dipolar cycloaddition between N-4-Tert-Benzylidene nitrone and maleimide in imidazolium-based ionic liquids (ILs) at 25 °C. Cycloaddition between nitrone 1 and maleimide 2 give diastereoisomeric adducts with 1:1 and 1:2 trans/cis ratio in two ionic liquids, [Bmim][PF6] and [Bmim][BF4], respectively. [Bmim][PF6] give the desired cycloadducts in 43% yield compared to only 18% yield in [Bmim][BF4]. In comparison, when the similar reaction was conducted in chloroform, the diasteroeisomeric mixture favoured trans isomer in 6:0.2 ratio. We reasoned that the repulsive van der Waals interactions favouring exo transition state was assisted by imidazolium ionic liquids. Thus, ILs have shown great potential as second reaction media in dipolar cycloaddition reactions.

Original languageMalay
Pages (from-to)1241-1246
Number of pages6
JournalMalaysian Journal of Analytical Sciences
Volume20
Issue number6
DOIs
Publication statusPublished - 2016

Fingerprint

Ionic Liquids
Cycloaddition
Chloroform
Isomers
maleimide
nitrones
1-butyl-3-methylimidazolium hexafluorophosphate

ASJC Scopus subject areas

  • Analytical Chemistry

Cite this

@article{f9ac3e8f90fe4ef2a2ba4bc2006b4617,
title = "Sintesis sebatian isoxazolidina melalui tindakbalas 1,3-dwikutub pensiklotambahan N-4-tetra-benzilidina nitron dan maleimida dalam cecair ionik berasaskan imidazolium",
abstract = "The development of environmentally friendly methodologies for pericyclic reactions such as Diels Alder reaction is astonishing. Nevertheless, this is still scarce for the rest of pericyclic reactions. In this work, diastereosiomeric cycloadducts were formed via 1,3-dipolar cycloaddition between N-4-Tert-Benzylidene nitrone and maleimide in imidazolium-based ionic liquids (ILs) at 25 °C. Cycloaddition between nitrone 1 and maleimide 2 give diastereoisomeric adducts with 1:1 and 1:2 trans/cis ratio in two ionic liquids, [Bmim][PF6] and [Bmim][BF4], respectively. [Bmim][PF6] give the desired cycloadducts in 43{\%} yield compared to only 18{\%} yield in [Bmim][BF4]. In comparison, when the similar reaction was conducted in chloroform, the diasteroeisomeric mixture favoured trans isomer in 6:0.2 ratio. We reasoned that the repulsive van der Waals interactions favouring exo transition state was assisted by imidazolium ionic liquids. Thus, ILs have shown great potential as second reaction media in dipolar cycloaddition reactions.",
keywords = "1,3-dipolar cycloaddition, Imidazolium ionic liquids, Pericyclic reactions",
author = "Johari, {Nur Liyana Sakinah} and Poad, {Siti Nashwa Mohd} and Hassan, {Nur Hasyareeda} and Hassan, {Nurul Izzaty}",
year = "2016",
doi = "10.17576/mjas-2016-2006-02",
language = "Malay",
volume = "20",
pages = "1241--1246",
journal = "Malaysian Journal of Analytical Sciences",
issn = "1394-2506",
publisher = "Faculty of Science and Technology, Universiti Kebangsaan Malaysia",
number = "6",

}

TY - JOUR

T1 - Sintesis sebatian isoxazolidina melalui tindakbalas 1,3-dwikutub pensiklotambahan N-4-tetra-benzilidina nitron dan maleimida dalam cecair ionik berasaskan imidazolium

AU - Johari, Nur Liyana Sakinah

AU - Poad, Siti Nashwa Mohd

AU - Hassan, Nur Hasyareeda

AU - Hassan, Nurul Izzaty

PY - 2016

Y1 - 2016

N2 - The development of environmentally friendly methodologies for pericyclic reactions such as Diels Alder reaction is astonishing. Nevertheless, this is still scarce for the rest of pericyclic reactions. In this work, diastereosiomeric cycloadducts were formed via 1,3-dipolar cycloaddition between N-4-Tert-Benzylidene nitrone and maleimide in imidazolium-based ionic liquids (ILs) at 25 °C. Cycloaddition between nitrone 1 and maleimide 2 give diastereoisomeric adducts with 1:1 and 1:2 trans/cis ratio in two ionic liquids, [Bmim][PF6] and [Bmim][BF4], respectively. [Bmim][PF6] give the desired cycloadducts in 43% yield compared to only 18% yield in [Bmim][BF4]. In comparison, when the similar reaction was conducted in chloroform, the diasteroeisomeric mixture favoured trans isomer in 6:0.2 ratio. We reasoned that the repulsive van der Waals interactions favouring exo transition state was assisted by imidazolium ionic liquids. Thus, ILs have shown great potential as second reaction media in dipolar cycloaddition reactions.

AB - The development of environmentally friendly methodologies for pericyclic reactions such as Diels Alder reaction is astonishing. Nevertheless, this is still scarce for the rest of pericyclic reactions. In this work, diastereosiomeric cycloadducts were formed via 1,3-dipolar cycloaddition between N-4-Tert-Benzylidene nitrone and maleimide in imidazolium-based ionic liquids (ILs) at 25 °C. Cycloaddition between nitrone 1 and maleimide 2 give diastereoisomeric adducts with 1:1 and 1:2 trans/cis ratio in two ionic liquids, [Bmim][PF6] and [Bmim][BF4], respectively. [Bmim][PF6] give the desired cycloadducts in 43% yield compared to only 18% yield in [Bmim][BF4]. In comparison, when the similar reaction was conducted in chloroform, the diasteroeisomeric mixture favoured trans isomer in 6:0.2 ratio. We reasoned that the repulsive van der Waals interactions favouring exo transition state was assisted by imidazolium ionic liquids. Thus, ILs have shown great potential as second reaction media in dipolar cycloaddition reactions.

KW - 1,3-dipolar cycloaddition

KW - Imidazolium ionic liquids

KW - Pericyclic reactions

UR - http://www.scopus.com/inward/record.url?scp=85003467486&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85003467486&partnerID=8YFLogxK

U2 - 10.17576/mjas-2016-2006-02

DO - 10.17576/mjas-2016-2006-02

M3 - Article

VL - 20

SP - 1241

EP - 1246

JO - Malaysian Journal of Analytical Sciences

JF - Malaysian Journal of Analytical Sciences

SN - 1394-2506

IS - 6

ER -