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

45 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

UR - https://www.scopus.com/pages/publications/84862010356

UR - https://www.scopus.com/pages/publications/84862010356#tab=citedBy

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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