New approach for the synthesis of 1-aryl- and 1-heteroaryl-5-nitrouracil derivatives |
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Authors: | Andrzej Gondela |
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Institution: | Department of Organic Chemistry, Biochemistry and Biotechnology, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, Poland |
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Abstract: | 1-(2,4-Dinitrophenyl)-5-nitrouracil and its 3-methyl derivatives were synthesized and used as substrates in reaction with aromatic amines and amino pyridines. In the reaction of aniline with 1-(2,4-dinitrophenyl)-5-nitrouracil, only the acyclic adduct was isolated. When 1-(2,4-dinitrophenyl)-3-methyl-5-nitrouracil was treated with aniline and other aromatic amines or amino pyridines, the desired 1-aryl-5-nitrouracil derivatives were obtained in satisfactory yield. The influence of the free H-3 proton present in the uracil ring on the course of the reaction is discussed. |
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Keywords: | 1-(2 4-Dinitrophenyl)-5-nitrouracil 1-Aryl-5-nitrouracil 3-Methyl-1-(pyridyl)-5-nitrouracil ANRORC type reaction Nucleophilic aromatic substitution |
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