Skip to main content
SpringerLink
Log in

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

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

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 

Download references

Author information

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
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. M. Ivanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. D. Daeva
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to L. M. Mironovich.

Additional information

Conflict of Interests

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.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

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

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428019070066

Keywords

Search

Navigation