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Synthesis and chemical properties of 8-lithio-4-oxopyrazolo[5,1-c][1,2,4]triazines

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Abstract

Unstable under normal conditions sodium and lithium 3-tert-butyl-8-lithio-7-R-4-oxopyrazolo[5,1-c][1,2,4]triazin-1-ides were generated for the first time by the reaction of 8-bromo-7-R-3-tert-butyl-4-oxopyrazolo[5,1-c][1,2,4]triazines (R = H, NHCOCF3) with BunLi in THF in the −97H÷−84 °C temperature range. The triazinides were trapped in the reactions with various electrophiles (H2O, CH3I, ArCHO, DMF, R1COCl) to selectively synthesize new C(8)-functionalized 4-oxopyrazolo[5,1-c][1,2,4]triazines.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    S. M. Ivanov, N. G. Kolotyrkina & A. M. Shestopalov

  2. Southwestern State University, 94 ul. 50 let Oktyabrya, 305040, Kursk, Russian Federation

    L. M. Mironovich

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  1. S. M. Ivanov
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  2. L. M. Mironovich
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  3. N. G. Kolotyrkina
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  4. A. M. Shestopalov
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Correspondence to S. M. Ivanov.

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Ivanov, S.M., Mironovich, L.M., Kolotyrkina, N.G. et al. Synthesis and chemical properties of 8-lithio-4-oxopyrazolo[5,1-c][1,2,4]triazines. Russ Chem Bull 68, 614–622 (2019). https://doi.org/10.1007/s11172-019-2464-9

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  • DOI: https://doi.org/10.1007/s11172-019-2464-9

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