Facile synthesis of 4-arylidene-5-imidazolinones as synthetic analogs of fluorescent protein chromophore |
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| Authors: | 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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| Institution: | 1. Department of Chemistry, National Taiwan Normal University, Taipei 11677, Taiwan;2. Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 80708, Taiwan |
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| 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. |
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