Chinese Journal of Organic Chemistry >
Synthesis of 4-Amino-5-biphenyloxy-3-halo-2(5H)-furanones
Received date: 2015-05-18
Revised date: 2015-06-27
Online published: 2015-07-08
Supported by
Project supported by the Natural Science Foundation of Guangdong Province (Nos. 2014A030313429, S2011010001556), the 3rd Talents Special Funds of Guangdong Higher Education (No. Guangdong-Finance-Education [2011]431), the National Natural Science Foundation of China (No. 31200439) and the Natural Science Project of Guangdong Food and Drug Vocational College (No. 2014YZ007).
Two novel 5-biphenyloxy-3,4-dihalo-2(5H)-furanones are synthesized via the direct dehydrative etherification reactions of biphenyl-4-ol with mucochloric acid and mucobromic acid, respectively, using sulfuric acid as a catalyst in toluene at reflux temperature. Taking them as intermediates, the tandem Michael addition-elimination reaction with different representative aliphatic amines is carried out in the presence of KF as a base and catalyst at room temperature. Sixteen 4-amino-5-biphenyloxy-3-halo-2(5H)-furanones are obtained, and the isolated yields are 43%～79% (mostly over 55%). The structures of all newly synthesized compounds were systematically characterized by FTIR, UV, 1H NMR, 13C NMR, MS and elemental analysis. This investigation affords an important novel strategy for the synthesis of different 2(5H)-furanone derivatives having potential bioactivity, especially for the synthesis of 2(5H)-furanones simultaneously with biphenyl and amino structure.
Ye Bin , Mo Guangzhen , Guan Litao , Wu Yancheng , Chen Renhong , Wang Zhaoyang . Synthesis of 4-Amino-5-biphenyloxy-3-halo-2(5H)-furanones[J]. Chinese Journal of Organic Chemistry, 2015 , 35(11) : 2420 -2428 . DOI: 10.6023/cjoc201505030
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