Adamantylation of 3-Nitro- and 3-Ethoxycarbonyl-1,2,4-triazolo[5,1-c]-1,2,4-triazin-4-ones |
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| Authors: | Ulomskii E N Deev S L Tkachev A V Moiseev I K Rusinov V L |
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| Institution: | (1) Ural State Technical University, Yekaterinburg, 620002, Russia;(2) Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, Novosibirsk, Russia;(3) Samara State Technical University, Samara, Russia |
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| Abstract: | Reaction of 3-nitro- and 3-ethoxycarbonyl-1,2,4-triazolo5,1-c]-1,2,4-triazin-4-ones with 1-adamantanol (or 1-adamantyl nitrate) in concentrated sulfuric acid or with 1-bromoadamantane in sulfolane affords N-adamantyl derivatives. The adamantylation of 3-nitro-1,4-dihydro-7H-1,2,4-triazolo5,1-c]-1,2,4-triazin-4-one yields a mixture of N8- and N1-isomers that undergo interconversion in concentrated sulfuric acid along intermolecular mechanism. |
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