A novel tandem cyclization of condensed 2,3-dialkynylpyrazines into [1,2,3]triazolo[1′,5′;1,2]pyrido[3,4-b]pyrazines promoted by sodium azide |
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Authors: | AV Gulevskaya Shee Van Dang AF Pozharskii AN Chekhlov |
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Institution: | a Department of Chemistry, Southern Federal University, Zorge 7, Rostov-on-Don 344090, Russian Federation b Institute of Problems of Chemical Physics, Russian Academy of Sciences, Semenov av. 1, 142432 Chernogolovka, Moscow Region, Russian Federation |
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Abstract: | 6,7-Dialkynyl-1,3-dimethylpteridine-2,4(1H,3H)-diones and 2,3-dialkynylquinoxalines have been shown to react with sodium azide in DMF at room temperature giving rise 9,11-dimethyl-1,2,3]triazolo1′,5′;1,2]pyrido4,3-g]pteridine-8,10(9H,11H)-diones and 1,2,3]triazolo1′,5′;1,2]pyrido3,4-b]quinoxalines. A novel tandem cyclization involves 1,3-dipolar cycloaddition of an azide ion to the carbon-carbon triple bond followed by intramolecular nucleophilic addition of the intermediate 1,2,3-triazole N-anion to another C C bond. |
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