Dehydrative Cyclization of Hydrazones: Synthesis of Pyrazolo and Pyrazolyl Quinoxalines |
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| Authors: | Ahmed Mousaad Laila Awad Nivine El Shimy El Sayed H El Ashry |
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| Institution: | Chemistry Department Faculty of Science , Alexandria University , Alexandria, Egypt |
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| Abstract: | Abstract A number of 3-(l-arylhydrazono-D-erythro-2,3,4-trihydroxybutyl)-6,7-dimethyl-lH-quinoxalin-2-ones (6–8) as well as the semi-and thiosemicarbazones have been prepared. Their periodate oxidation afforded the corresponding 3-(1-arylhydrazono-glyoxal-l-ýl)-6,7-dimethyl-lH-quinoxalin-2-ones (11–13), and their methylation gave 3-(l-arylhydrazono-D-erythro-2,3,4-trihydroxybutyl)-1,6,7-trimethyl-quinoxalin-2-ones (15–17). The action of alkali on the starting hydrazones (6–8) caused a loss of one mole of water to give 1-aryl-6,7-dimethyl-3-(D-erythro-glycerol-l-yl)-flavazoles (18–20) while the action of acetic anhydride afforded 3-(5-acetoxymethyl-l-arylpyrazol-3-yl)-6,7-dimethyl-lH-quinoxalin-2-ones (21–23). |
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