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

Research output: Contribution to journalArticle

30 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 languageEnglish
Pages (from-to)5898-5907
Number of pages10
JournalTetrahedron
Volume68
Issue number29
DOIs
Publication statusPublished - 2012 Jul 22

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Chromophores
Cyclization
Amines
Proteins
Derivatives
trifluoromethyloxazolinone
pyridine

Keywords

  • Acrylamide
  • Fluorescent protein chromophore
  • GFP
  • Imidazolinone
  • Oxazolinone

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Facile synthesis of 4-arylidene-5-imidazolinones as synthetic analogs of fluorescent protein chromophore. / Lee, Cheng Yu; Chen, Yun Chung; Lin, Hao Chun; Jhong, Yuandong; Chang, Chih Wei; Tsai, Ching Hua; Kao, Chai Lin; Chien, Tun-Cheng.

In: Tetrahedron, Vol. 68, No. 29, 22.07.2012, p. 5898-5907.

Research output: Contribution to journalArticle

Lee, Cheng Yu ; Chen, Yun Chung ; Lin, Hao Chun ; Jhong, Yuandong ; Chang, Chih Wei ; Tsai, Ching Hua ; Kao, Chai Lin ; Chien, Tun-Cheng. / Facile synthesis of 4-arylidene-5-imidazolinones as synthetic analogs of fluorescent protein chromophore. In: Tetrahedron. 2012 ; Vol. 68, No. 29. pp. 5898-5907.
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AU - Chang, Chih Wei

AU - Tsai, Ching Hua

AU - Kao, Chai Lin

AU - Chien, Tun-Cheng

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