Diastereoselective synthesis of 3-tert-butyl-3,4-dihydropyrazolo[5,1-c][1,2,4]triazine-3,4-diyl dicarboxylates |
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| Authors: | Sergey M Ivanov Andrey S Dmitrenok Konstantin A Lyssenko |
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| Institution: | 1. N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospekt, 47, Moscow 119991, Russia;2. D.I. Mendeleev University of Chemical Technology of Russia, Miusskaya Ploshchad'', 9, Moscow 125047, Russia;3. A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova St. 28, Moscow 119334, Russia;4. M.V. Lomonosov Moscow State University, Leninskiye Gory, 1, Moscow 119991, Russia |
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| Abstract: | The reactions of 3-tert-butyl-7-R1-8-R2-pyrazolo5,1-c]1,2,4]triazines (R1 = H, Br; R2 = Me, n-Bu) with N-bromosuccinimide in the presence of R3CO2H (R3 = Me, t-Bu, Ph) afforded novel diastereomerically pure 3-tert-butyl-7-R1-8-R2-3,4-dihydropyrazolo5,1-c]1,2,4]triazine-3,4-diyl dicarboxylates. The structures of the isolated products were established on the basis of IR, 1H, 13C, 2D NOESY NMR, high resolution mass spectrometry and X-ray single-crystal analysis. The steric and mechanistic origins of the observed regio- and stereoselectivity were also discussed. |
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| Keywords: | Corresponding author 1 2 4-Triazine Solvolytic bromination X-ray diffraction |
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