Facile synthesis of 4-arylidene-5-imidazolinones as synthetic analogs of fluorescent protein chromophore

Cheng Yu Lee; Yun Chung Chen; Hao Chun Lin; Yuandong Jhong; Chih Wei Chang; Ching Hua Tsai; Chai Lin Kao; Tun Cheng Chien

doi:10.1016/j.tet.2012.04.102

Facile synthesis of 4-arylidene-5-imidazolinones as synthetic analogs of fluorescent protein chromophore

Cheng Yu Lee, Yun Chung Chen, Hao Chun Lin, Yuandong Jhong, Chih Wei Chang, Ching Hua Tsai, Chai Lin Kao, Tun Cheng Chien^*

^*Corresponding author for this work

Department of Chemistry

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

40 Citations (Scopus)

Abstract

A facile and effective synthesis for a wide variety of 4-arylidene-5- imidazolinone derivatives was developed. 4-Arylidene-5-oxazolinones were prepared by Erlenmeyer azlactone synthesis from N-acylglycines and arylaldehydes. The ring-opening reactions of the 4-arylidene-5-oxazolinones with primary amines afforded 2-acylamino-3-arylacrylamides in excellent yields. A new dehydrative cyclization of the 2-acylamino-3-arylacrylamides in pyridine under reflux furnished the corresponding 4-arylidene-5-imidazolinones in good yields.

Original language	English
Pages (from-to)	5898-5907
Number of pages	10
Journal	Tetrahedron
Volume	68
Issue number	29
DOIs	https://doi.org/10.1016/j.tet.2012.04.102
Publication status	Published - 2012 Jul 22

Keywords

Acrylamide
Fluorescent protein chromophore
GFP
Imidazolinone
Oxazolinone

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2012.04.102

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@article{bb4eaccecfa945aab4ce113ac050ea1d,

title = "Facile synthesis of 4-arylidene-5-imidazolinones as synthetic analogs of fluorescent protein chromophore",

abstract = "A facile and effective synthesis for a wide variety of 4-arylidene-5- imidazolinone derivatives was developed. 4-Arylidene-5-oxazolinones were prepared by Erlenmeyer azlactone synthesis from N-acylglycines and arylaldehydes. The ring-opening reactions of the 4-arylidene-5-oxazolinones with primary amines afforded 2-acylamino-3-arylacrylamides in excellent yields. A new dehydrative cyclization of the 2-acylamino-3-arylacrylamides in pyridine under reflux furnished the corresponding 4-arylidene-5-imidazolinones in good yields.",

keywords = "Acrylamide, Fluorescent protein chromophore, GFP, Imidazolinone, Oxazolinone",

author = "Lee, {Cheng Yu} and Chen, {Yun Chung} and Lin, {Hao Chun} and Yuandong Jhong and Chang, {Chih Wei} and Tsai, {Ching Hua} and Kao, {Chai Lin} and Chien, {Tun Cheng}",

note = "Funding Information: This work was supported by Research Grants 99-2113-M-003-003 - and 99-2320-B-037-012-MY3 from the National Science Council, Taiwan , NTNU100-D-06 from National Taiwan Normal University and from Kaohsiung Medical University Research Foundation . We are grateful to the National Center for High-performance Computing of Taiwan for the electronic resources and facilities. ",

year = "2012",

month = jul,

day = "22",

doi = "10.1016/j.tet.2012.04.102",

language = "English",

volume = "68",

pages = "5898--5907",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "29",

}

TY - JOUR

T1 - Facile synthesis of 4-arylidene-5-imidazolinones as synthetic analogs of fluorescent protein chromophore

AU - Lee, Cheng Yu

AU - Chen, Yun Chung

AU - Lin, Hao Chun

AU - Jhong, Yuandong

AU - Chang, Chih Wei

AU - Tsai, Ching Hua

AU - Kao, Chai Lin

AU - Chien, Tun Cheng

N1 - Funding Information: This work was supported by Research Grants 99-2113-M-003-003 - and 99-2320-B-037-012-MY3 from the National Science Council, Taiwan , NTNU100-D-06 from National Taiwan Normal University and from Kaohsiung Medical University Research Foundation . We are grateful to the National Center for High-performance Computing of Taiwan for the electronic resources and facilities.

PY - 2012/7/22

Y1 - 2012/7/22

N2 - A facile and effective synthesis for a wide variety of 4-arylidene-5- imidazolinone derivatives was developed. 4-Arylidene-5-oxazolinones were prepared by Erlenmeyer azlactone synthesis from N-acylglycines and arylaldehydes. The ring-opening reactions of the 4-arylidene-5-oxazolinones with primary amines afforded 2-acylamino-3-arylacrylamides in excellent yields. A new dehydrative cyclization of the 2-acylamino-3-arylacrylamides in pyridine under reflux furnished the corresponding 4-arylidene-5-imidazolinones in good yields.

AB - A facile and effective synthesis for a wide variety of 4-arylidene-5- imidazolinone derivatives was developed. 4-Arylidene-5-oxazolinones were prepared by Erlenmeyer azlactone synthesis from N-acylglycines and arylaldehydes. The ring-opening reactions of the 4-arylidene-5-oxazolinones with primary amines afforded 2-acylamino-3-arylacrylamides in excellent yields. A new dehydrative cyclization of the 2-acylamino-3-arylacrylamides in pyridine under reflux furnished the corresponding 4-arylidene-5-imidazolinones in good yields.

KW - Acrylamide

KW - Fluorescent protein chromophore

KW - GFP

KW - Imidazolinone

KW - Oxazolinone

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U2 - 10.1016/j.tet.2012.04.102

DO - 10.1016/j.tet.2012.04.102

M3 - Article

AN - SCOPUS:84862010356

SN - 0040-4020

VL - 68

SP - 5898

EP - 5907

JO - Tetrahedron

JF - Tetrahedron

IS - 29

ER -

Facile synthesis of 4-arylidene-5-imidazolinones as synthetic analogs of fluorescent protein chromophore

Abstract

Keywords

ASJC Scopus subject areas

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