Synthesis of new 5-aza-isosteres of guanine—5-aminosubstituted 1,2,4-triazolo[1,5-a]-1,3,5-triazin-7-ones |
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| Authors: | Vladimir V Bakharev Victor E Parfenov Irina V Ul'yankina Anna V Zavodskaya Evgeniya V Selezneva Alexander A Gidaspov Oleg S Eltsov Pavel A Slepukhin |
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| Institution: | 1. Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia;2. Ural Federal University, 19 Mira St., Ekaterinburg 620002, Russia;3. I.Ya. Postovsky Institute of Organic Synthesis (Ural Branch of RAS), 22 S. Kovalevskaya St., Ekaterinburg 620219, Russia |
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| Abstract: | The reaction of 4-amino-substituted 6-hydrazinyl-1,3,5-triazin-2(1H)-ones with orthoformate proceeds via the Dimroth-type rearrangement to give 5-amino-substituted 1,2,4-triazolo1,5-a]-1,3,5-triazine-7-ones. IR, NMR and X-ray studies have shown that the only product of the reaction was the 1,5-a]-isomer as prototropic 3H- and 6H-tautomers. |
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| Keywords: | Nitrogen heterocycles Cyclization Fused-ring systems Tautomerism Rearrangement |
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