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Alkylation of 3-tert-Butylpyrimido[4′,5′:3,4]pyrazolo[5,1-c]-[1,2,4]triazine-4,10(1H,9H)-diones and -dithiones

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Abstract

The condensation of 7-amino-1-benzyl-3-tert-butyl-4-oxo-1,4-dihydropyrazolo[5,1-c][1,2,4]triazine-8-carbonitrile with formic acid afforded 1-benzyl-3-tert-butylpyrimido[4′,5′:3,4]pyrazolo[5,1-c][1,2,4]-triazine-4,10(1H,9H)-dione which was also synthesized by alkylation of 3-tert-butylpyrimido[4′,5′: 3,4]pyrazolo[5,1-c][1,2,4]triazine-4,10(1H,9H)-dione with benzyl chloride. The reactions of 1-benzyl- and 1-butyl-3-tert-butylpyrimido[4′,5′: 3,4]pyrazolo[5,1-c][1,2,4]triazine-4,10(1H,9H)-diones with butyl bromide and benzyl chloride, respectively, under harsh conditions gave substitution products at the N9 atom, the corresponding 1-benzyl-9-butyl and 9-benzyl-1-butyl derivatives. The alkylation of 3-tert-butyl pyrimido[4′,5′: 3,4]-pyrazolo[5,1-c][1,2,4]triazine-4,10(1H,9H)-dithione and its 8-methyl derivative in alkaline medium led to the formation of alkyl derivatives at the sulfur atom in the 10-position.

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References

  1. Mironovich, L.M. and Ivanov, S.M., Aktual’nye voprosy tekhnicheskikh nauk: teoreticheskii i prakticheskii aspekty. Kollektivnaya monografiya (Current Problems of Technical Sciences: Theoretical and Practical Aspects. A Collection of Papers), Grigor’ev, I.A., Ed., Ufa: Aeterna, 2017, p. 51.

  2. Konovalov, A.I., Antipin, I.S., Burilov, V.A., Madzhidov, T.I., Kurbangalieva, A.R., Nemtarev, A.V., Solovieva, S.E., Stoikov, I.I. Mamedov, V.A., Zakharova, L.Ya., Gavrilova, E.L., Sinyashin, O.G., Balova, I.A., Vasilyev, A.V., Zenkevich, I.G., Krasavin, M.Yu., Kuznetsov, M.A., Molchanov, A.P., Novikov, M.S., Nikolaev, V.A., Rodina, L.L., Khlebnikov, A.F., Beletskaya, I.P., Vatsadze, S.Z., Gromov, S.P., Zyk, N.V., Lebedev, A.T., Lemenovskii, D.A., Petrosyan, V.S., Nenaidenko, V.G., Negrebetskii, V.V., Baukov, Yu.I., Shmigol’, T.A., Korlyukov, A.A., Tikhomirov, A.S., Shchekotikhin, A.E., Traven’, V.F., Voskresenskii, L.G., Zubkov, F.I., Golubchikov, O.A., Semeikin, A.S., Berezin, D.B., Stuzhin, P.A., Filimonov, V.D., Krasnokutskaya, E.A., Fedorov, A.Yu., Nyuchev, A.V., Orlov, V.Yu., Begunov, R.S., Rusakov, A.I., Kolobov, A.V., Kofanov, E.R., Fedotova, O.V., Egorova, A.Yu., Charushin, V.N., Chupakhin, O.N., Klimochkin, Yu.N., Osyanin, V.A., Reznikov, A.N., Fisyuk, A.S., Sagitullina, G.P., Aksenov, A.V., Aksenov, N.A., Grachev, M.K., Maslennikova, V.I., Koroteev, M.P., Brel’, A.K., Lisina, S.V., Medvedeva, S.M., Shikhaliev, Kh.S., Suboch, G.A., Tovbis, M.S., Mironovich, L.M., Ivanov, S.M., Kurbatov, S.V., Kletskii, M.E., Burov, O.N., Kobrakov, K.I., and Kuznetsov, D.N., Russ. J. Org. Chem., 2018, vol. 54, p. 157. doi: https://doi.org/10.1134/S107042801802001X

    Article  CAS  Google Scholar 

  3. Mironovich, L.M., Ivanov, S.M., Chizhov, A.O., and Daeva, E.D., Russ. J. Org. Chem., 2017, vol. 53, p. 577. doi https://doi.org/10.1134/S10704280170401334

    Article  CAS  Google Scholar 

  4. Ivanov, S.M., Mironovich, L.M., Solyev, P.N., Rodinovskaya, L.A., and Shestopalov, A.M., J. Heterocycl. Chem., 2018, vol. 55, p. 545. doi https://doi.org/10.1002/jhet.3064

    Article  CAS  Google Scholar 

  5. Ivanov, S.M., Mironovich, L.M., Rodinovskaya, L.A., and Shestopalov, A.M., Tetrahedron Lett., 2017, vol. 58, p. 1851. doi https://doi.org/10.1016/j.tetlet.2017.03.083

    Article  CAS  Google Scholar 

  6. Ivanov, S.M., Mironovich, L.M., Rodinovskaya, L.A., and Shestopalov, A.M., Russ. Chem. Bull., Int. Ed., 2018, vol. 67, p. 1482. doi https://doi.org/10.1007/s11172-018-2243-z

    Article  CAS  Google Scholar 

  7. Ivanov, S.M., Mironovich, L.M., Rodinovskaya, L.A., and Shestopalov, A.M., Russ. Chem. Bull., Int. Ed., 2018, vol. 67, p. 1487. doi https://doi.org/10.1007/s11172-018-2244-y

    Article  CAS  Google Scholar 

  8. Charushin, V., Rusinov, V., and Chupakhin, O., Comprehensive Heterocyclic Chemistry III, Katritzky, A.R., Ramsden, C.A., Scriven, E.F.V., and Taylor, R.J.K., Eds., Amsterdam: Elsevier, 2008, vol. 9, p. 95. doi https://doi.org/10.1016/B978-008044992-0.00802-6.9

  9. Ivanov, S.M., Mironovich, L.M., Rodinovskaya, L.A., and Shestopalov, A.M., Russ. Chem. Bull., Int. Ed., 2017, vol. 66, p. 1126. doi https://doi.org/10.1007/s11172-017-1865-x

    Article  CAS  Google Scholar 

  10. Mironovich, L.M., Kostina, M.V., and Podol’nikova, A.Yu., Russ. J. Org. Chem., 2013, vol. 49, p. 758. doi https://doi.org/10.1134/S1070428013050230

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Southwest State University, Kursk, Russia

    L. M. Mironovich

  2. Zelinskii Institute of Organic Chemistry, Moscow, Russia

    S. M. Ivanov & E. D. Daeva

Authors
  1. L. M. Mironovich
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  2. S. M. Ivanov
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  3. E. D. Daeva
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Correspondence to L. M. Mironovich.

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The authors declare the absence of conflict of interests.

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 7, pp. 1055–1062.

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Mironovich, L.M., Ivanov, S.M. & Daeva, E.D. Alkylation of 3-tert-Butylpyrimido[4′,5′:3,4]pyrazolo[5,1-c]-[1,2,4]triazine-4,10(1H,9H)-diones and -dithiones. Russ J Org Chem 55, 958–963 (2019). https://doi.org/10.1134/S1070428019070066

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