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

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31 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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Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Lee, C. Y., Chen, Y. C., Lin, H. C., Jhong, Y., Chang, C. W., Tsai, C. H., Kao, C. L., & Chien, T. C. (2012). Facile synthesis of 4-arylidene-5-imidazolinones as synthetic analogs of fluorescent protein chromophore. Tetrahedron, 68(29), 5898-5907. https://doi.org/10.1016/j.tet.2012.04.102