Simple and efficient access to pyrazine-2,5- and -2,6-dicarbaldehydes |
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Authors: | Radek Coufal Markéta Prusková Ivana Císařová Dušan Drahoňovský |
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Institution: | 1. Charles University in Prague, Faculty of Science, Department of Physical and Macromolecular Chemistry, Prague, Czech Republic;2. Charles University in Prague, Faculty of Science, Department of Organic Chemistry, Prague, Czech Republiccoufalr@natur.cuni.cz;4. Charles University in Prague, Faculty of Science, Department of Organic Chemistry, Prague, Czech Republic;5. Charles University in Prague, Faculty of Science, Department of Inorganic Chemistry, Prague, Czech Republic;6. Charles University in Prague, Faculty of Science, Department of Organic Chemistry, Prague, Czech Republic |
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Abstract: | Efficient two-step synthesis of pyrazine-2,5- and -2,6-dicarbaldehydes is presented that consists of transformation of easily available corresponding dimethylpyrazines to distyryl derivatives and oxidation of the latter with the tandem system of osmium tetroxide/periodate ions. The proper choice of dehydration agent in the first reaction step and the good efficiency of the subsequent low-temperature oxidation are the key points of the developed protocol. Other examined synthesis routes were much less successful, but one of them leads to new powerful routes to methyl (5-hydroxymethyl)pyrazine-2-carboxylate and dimethyl 3,4-dihydropyrazine-2,6-dicarboxylate. Previously unknown characteristics of the title compounds are reported. |
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Keywords: | Dimethyl 3 4-dihydropyrazine-2 6-dicarboxylate distyrylpyrazine methyl (5-hydroxymethyl)pyrazine-2-carboxylate pyrazinedicarbaldehydes tandem oxidation system |
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