BmimOAc ionic liquid: A highly efficient catalyst for synthesis of 3-aryl-2-oxazolidinones by direct condensation of 2-(arylamino) alcohols with diethyl carbonate

Elnazeer H.M. Elageed; Binshen Wang; Yongya Zhang; Shi Wu; Guohua Gao

doi:10.1016/j.molcata.2015.07.034

BmimOAc ionic liquid: A highly efficient catalyst for synthesis of 3-aryl-2-oxazolidinones by direct condensation of 2-(arylamino) alcohols with diethyl carbonate

Elnazeer H.M. Elageed, Binshen Wang, Yongya Zhang, Shi Wu, Guohua Gao

School of Chemistry and Molecular Engineering

East China Normal University

Research output: Contribution to journal › Article › peer-review

24 Scopus citations

Abstract

An efficient convenient procedure for the synthesis of 3-aryl-2-oxazolidinones from 2-(arylamino) alcohols and diethyl carbonate (DEC) catalyzed by ionic liquids is described. The effects of reaction time, amount of catalyst and temperature were investigated. Excellent yields of products were obtained under the optimized reaction conditions, when using BmimOAc as a catalyst. An intermediate ethyl 2-(phenyl amino) ethyl carbonate was isolated and characterized. ¹H NMR spectroscopy and DFT calculations indicated that BmimOAc cooperatively activate the substrates through hydrogen bonding with its anion and cation sites. According to these results, a possible reaction mechanism was discussed.

Original language	English
Article number	9585
Pages (from-to)	271-277
Number of pages	7
Journal	Journal of Molecular Catalysis A: Chemical
Volume	408
DOIs	https://doi.org/10.1016/j.molcata.2015.07.034
State	Published - 1 Nov 2015

Keywords

Catalysis
Cooperative
Ionic liquids
Mechanism
Oxazolidinones

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10.1016/j.molcata.2015.07.034

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@article{5e87082f5d7445ef9208d2795674d133,

title = "BmimOAc ionic liquid: A highly efficient catalyst for synthesis of 3-aryl-2-oxazolidinones by direct condensation of 2-(arylamino) alcohols with diethyl carbonate",

abstract = "An efficient convenient procedure for the synthesis of 3-aryl-2-oxazolidinones from 2-(arylamino) alcohols and diethyl carbonate (DEC) catalyzed by ionic liquids is described. The effects of reaction time, amount of catalyst and temperature were investigated. Excellent yields of products were obtained under the optimized reaction conditions, when using BmimOAc as a catalyst. An intermediate ethyl 2-(phenyl amino) ethyl carbonate was isolated and characterized. 1H NMR spectroscopy and DFT calculations indicated that BmimOAc cooperatively activate the substrates through hydrogen bonding with its anion and cation sites. According to these results, a possible reaction mechanism was discussed.",

keywords = "Catalysis, Cooperative, Ionic liquids, Mechanism, Oxazolidinones",

author = "Elageed, \{Elnazeer H.M.\} and Binshen Wang and Yongya Zhang and Shi Wu and Guohua Gao",

note = "Publisher Copyright: {\textcopyright} 2015 Elsevier B.V.",

year = "2015",

month = nov,

day = "1",

doi = "10.1016/j.molcata.2015.07.034",

language = "英语",

volume = "408",

pages = "271--277",

journal = "Journal of Molecular Catalysis A: Chemical",

issn = "1381-1169",

publisher = "Elsevier B.V.",

}

BmimOAc ionic liquid: A highly efficient catalyst for synthesis of 3-aryl-2-oxazolidinones by direct condensation of 2-(arylamino) alcohols with diethyl carbonate. / Elageed, Elnazeer H.M.; Wang, Binshen; Zhang, Yongya et al.
In: Journal of Molecular Catalysis A: Chemical, Vol. 408, 9585, 01.11.2015, p. 271-277.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - BmimOAc ionic liquid

T2 - A highly efficient catalyst for synthesis of 3-aryl-2-oxazolidinones by direct condensation of 2-(arylamino) alcohols with diethyl carbonate

AU - Elageed, Elnazeer H.M.

AU - Wang, Binshen

AU - Zhang, Yongya

AU - Wu, Shi

AU - Gao, Guohua

PY - 2015/11/1

Y1 - 2015/11/1

N2 - An efficient convenient procedure for the synthesis of 3-aryl-2-oxazolidinones from 2-(arylamino) alcohols and diethyl carbonate (DEC) catalyzed by ionic liquids is described. The effects of reaction time, amount of catalyst and temperature were investigated. Excellent yields of products were obtained under the optimized reaction conditions, when using BmimOAc as a catalyst. An intermediate ethyl 2-(phenyl amino) ethyl carbonate was isolated and characterized. 1H NMR spectroscopy and DFT calculations indicated that BmimOAc cooperatively activate the substrates through hydrogen bonding with its anion and cation sites. According to these results, a possible reaction mechanism was discussed.

AB - An efficient convenient procedure for the synthesis of 3-aryl-2-oxazolidinones from 2-(arylamino) alcohols and diethyl carbonate (DEC) catalyzed by ionic liquids is described. The effects of reaction time, amount of catalyst and temperature were investigated. Excellent yields of products were obtained under the optimized reaction conditions, when using BmimOAc as a catalyst. An intermediate ethyl 2-(phenyl amino) ethyl carbonate was isolated and characterized. 1H NMR spectroscopy and DFT calculations indicated that BmimOAc cooperatively activate the substrates through hydrogen bonding with its anion and cation sites. According to these results, a possible reaction mechanism was discussed.

KW - Catalysis

KW - Cooperative

KW - Ionic liquids

KW - Mechanism

KW - Oxazolidinones

UR - https://www.scopus.com/pages/publications/84939529877

U2 - 10.1016/j.molcata.2015.07.034

DO - 10.1016/j.molcata.2015.07.034

M3 - 文章

AN - SCOPUS:84939529877

SN - 1381-1169

VL - 408

SP - 271

EP - 277

JO - Journal of Molecular Catalysis A: Chemical

JF - Journal of Molecular Catalysis A: Chemical

M1 - 9585

ER -

BmimOAc ionic liquid: A highly efficient catalyst for synthesis of 3-aryl-2-oxazolidinones by direct condensation of 2-(arylamino) alcohols with diethyl carbonate

Abstract

Keywords

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