Unexpected Reaction of Ethyl 4-(Chloromethyl)pyrazolo- [5,1-<Emphasis Type="Italic">c</Emphasis>][1,2,4]triazine-3-carboxylates with Thiourea and Its Mechanism |
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| Authors: | I V Ledenyova A V Falaleev Kh S Shikhaliev E A Ryzhkova F I Zubkov |
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| Institution: | 1.Voronezh State University,Voronezh,Russia;2.Peoples’ Friendship University of Russia,Moscow,Russia |
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| Abstract: | The reaction of ethyl 4-(chloromethyl)pyrazolo5,1-c]1,2,4]triazine-3-carboxylates with thiourea in dimethylformamide involves ANRORC rearrangement (Addition of the Nucleophile, Ring Opening, and Ring Closure) followed by N-formylation to give N-{5-(4-oxo-8-phenyl-1,4-dihydropyrazolo5,1-c]1,2,4]-triazin-3-yl)-1,3-triazol-2-yl}formamides whose structure was confirmed by X-ray analysis. The reaction mechanism has been studied by HPLC/MS. |
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