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Reduction and diazotization of ethyl 7-amino-3-tert-butyl-4-oxo-4,6-dihydropyrazolo[5,1-c][1,2,4]triazine-8-carboxylate

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Abstract

The ester group in ethyl 7-amino-3-tert-butyl-4-oxo-4,6-dihydropyrazolo[5,1-c][1,2,4]triazine-8-carboxylate was converted for the first time to methyl by the action of lithium tetrahydridoborate in the presence of boron trifluoride–diethyl ether complex. This reaction has almost no analogies among other classes of organic compounds. New difficultly accessible 7-chloro and 7-azido derivatives were synthesized via diazotization of the reduction product, and treatment of the latter with acetic anhydride afforded the exhaustively acetylated derivative. Diazotization of ethyl 7-amino-3-tert-butyl-4-oxo-4,6-dihydropyrazolo-[5,1-c][1,2,4]triazine-8-carboxylate, followed by reaction with sodium azide, gave the corresponding azide, and the product of azo coupling with ethyl acetoacetate failed to undergo intramolecular cyclization to tricyclic pyrazolo[3,2-c: 5,1-c′]bis[1,2,4]triazine system.

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References

  1. Hamama, W.S., El-Bana, G.G., Shaaban, S., Habib, O.M.O., and Zoorob, H.H., RSC Adv., 2016, vol. 6, p. 24010. doi 10.1039/c5ra26433b

    Article  CAS  Google Scholar 

  2. Mironovich, L.M. and Podol’nikova, A.Yu., Russ. J. Org. Chem., 2016, vol. 52, p. 453. doi 10.1134/S1070428016030283

    Article  CAS  Google Scholar 

  3. Mironovich, L.M. and Shcherbinin, D.V., Russ. J. Org. Chem., 2015, vol. 51, p. 292. doi 10.1134/S107042801502030X

    Article  CAS  Google Scholar 

  4. Mironovich, L.M. and Podol’nikova, A.Yu., Russ. J. Org. Chem., 2015, vol. 51, p. 397. doi: 10.1134/S1070428015030197

    Article  CAS  Google Scholar 

  5. Lane, C.F., Chem. Rev., 1976, vol. 76, p. 773. doi 10.1021/cr60304a005

    Article  CAS  Google Scholar 

  6. Zhu, H.-J. and Pittman, Ch.U., Synth. Commun., 2003, vol. 33, p. 1733. doi 10.1081/SCC-120018935

    Article  CAS  Google Scholar 

  7. Soai, K. and Ookawa, A., J. Org. Chem., 1986, vol. 51, p. 4000. doi 10.1021/jo00371a017

    Article  CAS  Google Scholar 

  8. Patra, P.K., Nishide, K., Fuji, K., and Node, M., Synthesis, 2004, p. 1003. doi 10.1055/s-2004-822338

    Google Scholar 

  9. Sonnet, Ph.E., J. Heterocycl. Chem., 1972, vol. 9, p. 1395. doi 10.1002/jhet.5570090636

    Article  CAS  Google Scholar 

  10. Mironovich, L.M. and Kostina, M.V., Chem. Heterocycl. Compd., 2012, vol. 47, no. 10, p. 1286. doi 10.1007/s10593-012-0904-7

    Article  CAS  Google Scholar 

  11. Tsedilin, A.M., Fakhrutdinov, A.N., Eremin, D.B., Zalesskiy, S.S., Chizhov, A.O., Kolotyrkina, N.G., and Ananikov, V.P., Mendeleev Commun., 2015, vol. 25, p. 454. doi 10.1016/j.mencom.2015.11.019

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Southwest State University, ul. 50 let Oktyabrya 94, Kursk, 305040, Russia

    L. M. Mironovich

  2. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Leninskii pr. 47, Moscow, 119991, Russia

    S. M. Ivanov, A. O. Chizhov & E. D. Daeva

Authors
  1. L. M. Mironovich
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  2. S. M. Ivanov
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  3. A. O. Chizhov
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  4. E. D. Daeva
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Correspondence to L. M. Mironovich.

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Original Russian Text © L.M. Mironovich, S.M. Ivanov, A.O. Chizhov, E.D. Daeva, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 4, pp. 571–575.

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Mironovich, L.M., Ivanov, S.M., Chizhov, A.O. et al. Reduction and diazotization of ethyl 7-amino-3-tert-butyl-4-oxo-4,6-dihydropyrazolo[5,1-c][1,2,4]triazine-8-carboxylate. Russ J Org Chem 53, 577–581 (2017). https://doi.org/10.1134/S1070428017040133

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  • DOI: https://doi.org/10.1134/S1070428017040133

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