Synthesis and reactions of 2,3-dimethylfuro[3,2-c]pyridines |
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Authors: | V Bobo?ík A Kruto?íková U Jordis |
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Institution: | (1) Department of Organic Chemistry, Faculty of Chemical Technology, Slovak Technical University, SK-81237 Bratislava, Slovakia;(2) Institute of Organic Chemistry, Technical University Vienna, A-1060 Wien, Austria |
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Abstract: | Summary A number of substituted 2,3-dimethylfuro3,2-c]pyridines was synthesized. 3-(4,5-Dimethyl-2-furyl)propenoic acid (1) was converted to the acid azide2, which in turn was cyclized to give 2,3-dimethyl-5H-furo3,2-c]pyridine-4-one (3) by heating at 240°C in Dowtherm. The pyridone3 was chlorinated with phosphorus oxychloride to give4, which was reduced with zinc and acetic acid to 2,3-dimethylfuro3,2-c]pyridine (5). Treatment of4 with several secondary heterocyclic amines led to compounds6a–6c. Reaction of pyridone3 with phosphorus pentasulfide rendered the thione7, which was methylated to8a. The 4-methoxy derivative8b was obtained from4 with sodium methoxide. 2,3,5-Trimethylfuro3,2-c]pyridine-4-one (9) was obtained by reaction of3 with methyl iodide.Dedicated to Professor Dr.Fritz Sauter on the occasion of his 65th birthday |
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Keywords: | 5H-Furo[3 2-c]pyridine-4-ones 5H-Furo[3 2-c]pyridine-4-thiones Furo[3 2-c]pyridine |
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