Abstract
A procedure has been developed for the synthesis of 6,7-dihydroindazoles and 7,8-dihydroquinazolines by reaction of 3,4-dihydroxanthone derivatives with 1,2- and 1,3-binucleophiles (hydrazine, guanidine). The reaction occurred under mild conditions (methanol, 20-65°C) with high yields.
Similar content being viewed by others
REFERENCES
Kubas, H., Meyer, U., Krueger, B., Hechenberger, M., Vanejevs, M., Zemribo, R., Kauss, V., Ambartsumova, R., Pyatkin, I., Polosukhin, A.I., and Abel, U., Bioorg. Med. Chem. Lett., 2013, vol. 23, no. 16, p. 4493. https://doi.org/10.1016/j.bmcl.2013.06.049
Beria, I., Ballinari, D., Bertrand, J.A., Borghi, D., Bossi, R.T., Brasca, M.G., Cappella, P., Caruso, M., Ceccarelli, W., Ciavolella, A., Cristiani, C., Croci, V., De Ponti, A., Fachin, G., Ferguson, R.D., Lansen, J., Moll, J.K., Pesenti, E., Posteri, H., Perego, R., Rocchetti, M., Storici, P., Volpi, D., and Valsasina, B., J. Med. Chem., 2010, vol. 53, p. 3532. https://doi.org/10.1021/jm901713n
Brasca, M.G., Amboldi, N., Ballinari, D., Cameron, A., Casale, E., Cervi, G., Colombo, M., Colotta, F., Croci, V., D’Alessio, R., Fiorentini, F., Isacchi, A., Mercurio, C., Moretti, W., Panzeri, A., Pastori, W., Pevarello, P., Quartieri, F., Roletto, F., Traquandi, G., Vianello, P., Vulpetti, A., and Ciomei, M., J. Med. Chem., 2009, vol. 52, p. 5152. https://doi.org/10.1021/jm9006559
Khlebnikova, T.S., Piven’, Yu.A., Zinovich, V.G., Baranovskii, A.V., Rusanov, E.B., Panibrat, O.V., Ogurtsova, S.E., and Lakhvich, F.A., Pharm. Chem. J., 2020, vol. 54, no. 7, p. 700. https://doi.org/10.1007/s11094-020-02258-z
Prajapat, P. and Talesara, G.L., J. Heterocycl. Chem., 2016, vol. 53, p. 1603. https://doi.org/10.1002/jhet.2471
Tonkikh, N.N., Strakov, A.Y., and Petrova, M.V., Chem. Heterocycl. Compd., 1998, vol. 34, p. 92. https://doi.org/10.1007/BF02290618
Strakova, I.A., Strakov, A.Y., and Petrova, M.V., Chem. Heterocycl. Compd., 2000, vol. 36, p. 847. https://doi.org/10.1007/BF02256921
Spanò, V., Montalbano, A., Carbone, A., Parrino, B., Diana, P., Cirrincione, G., and Barraja, P., Tetrahedron, 2013, vol. 69, p. 9839. https://doi.org/10.1016/j.tet.2013.09.003
Chernov, N.M., Shutov, R.V., Sharoyko, V.V., Kuz’mich, N.N., Belyakov, A.V., and Yakovlev, I.P., Eur. J. Org. Chem., 2017, vol. 2017, p. 2836. https://doi.org/10.1002/ejoc.201700310
Chernov, N.M., Ezhov, P.I., Shutov, R.V., and Yakovlev, I.P., Russ. J. Gen. Chem., 2020, vol. 90, no. 9, p. 1620. https://doi.org/10.1134/S1070363220090054
Chaudhary, R.P., Gautam, P., Gautam, D., and Mittal, I., J. Mol. Struct., 2021, vol. 1228, article ID 129710. https://doi.org/10.1016/j.molstruc.2020.129710
Chernov, N.M., Shutov, R.V., Potapova, A.E., and Yakovlev, I.P., Synthesis, 2020, vol. 52, no. 1, p. 40. https://doi.org/10.1055/s-0039-1690723
Funding
This study was performed under partial financial support by the Council for Grants at the President of the Russian Federation (project no. SP-2019) and in the framework of state assignment of the Ministry of Health of the Russian Federation (project no. AAAA-A20-120121790030-8).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
No conflict of interest was declared by the authors.
Additional information
Translated from Zhurnal Obshchei Khimii, 2021, Vol. 91, No. 7, pp. 1036–1041 https://doi.org/10.31857/S0044460X21070076.
Rights and permissions
About this article
Cite this article
Chernov, N.M., Lebedev, M.Y., Luk’yanenko, V.I. et al. Synthesis of 6,7-Dihydroindazole and 7,8-Dihydroquinazoline Derivatives from Ethyl 4,4-Dimethyl-9-oxo-3,4-dihydro-9H-xanthene-2-carboxylates. Russ J Gen Chem 91, 1305–1309 (2021). https://doi.org/10.1134/S1070363221070070
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363221070070