Abstract
Solvent-free reaction of 3,6-diaryl-1,2,4-triazine-5-carbonitriles with 2-amino-4-aryloxazoles was studied. In this case, the formation of 3- and 4-aryl-substituted pyridines (two isomeric products) in yields up to 20 and 27%, respectively, was found. This result is different from that for the reaction of 3-(2-pyridyl)-1,2,4-triazine-5-carbonitriles with these substrates. Thus, in this case, 2-amino-4-aryloxazoles act as synthetic analogues of arylacetylenes.
REFERENCES
Prokhorov, A.M. and Kozhevnikov, D.N., Chem. Heterocycl. Compd., 2012, vol. 48, p. 1153. https://doi.org/10.1007/s10593-012-1117-9
Foster Radleigh, A.A. and Willis, M.C., Chem. Soc. Rev., 2013, vol. 42, p. 63. https://doi.org/10.1039/c2cs35316d
Gonsalves, A.M.d.’A.R., Pinho e Melo, T.M.V.D., and Gilchrist, T.L., Tetrahedron, 1992, vol. 48, p. 6821. https://doi.org/10.1016/s0040-4020(01)89873-2
Gundala, S., Khasanov, A.F., Kopchuk, D.S., Starnovskaya, E.S., Shtaitz, Ya.K., Krinochkin, A.P., Gorbunov, E.B., Zyryanov, G.V., Padmavathi, V., and Chupakhin, O.N., Polycycl. Arom. Compd., 2022, vol. 42, no. 5, p. 1994. https://doi.org/10.1080/10406638.2020.1823858
Boger, D.L., Panek, J.S., and Meier, M.M., J. Org. Chem., 1982, vol. 47, no. 5, p. 895. https://doi.org/10.1021/jo00344a031
Sainz, Y.F., Raw, S.A., and Taylor, R.J.K., J. Org. Chem., 2005, vol. 70, no. 24, p. 10086. https://doi.org/10.1021/jo0518304
Dhar, R., Huehnermann, W., Kaempchen, T., Overheu, W., and Seitz, G., Chem. Ber., 1983, vol. 116, no. 1, p. 97. https://doi.org/10.1002/cber.19831160111
Fadel, S., Hajbi, Y., Khouili, M., Lazar, S., Suzenet, F., and Guillaumet, G., Beilstein J. Org. Chem., 2014, vol. 10, p. 282. https://doi.org/10.3762/bjoc.10.24
Jouha, J., Buttard, F., Lorion, M., Berthonneau, C., Khouili, M., Hiebel, M.-A., Guillaumet, G., Brière, J.-F., and Suzenet, F., Org. Lett., 2017, vol. 19, no. 18, p. 4770. https://doi.org/10.1021/acs.orglett.7b02132
Diring, S., Retailleau, P., and Ziessel, R., J. Org. Chem., 2007, vol. 72, p. 10181. https://doi.org/10.1021/jo7019866
Diring, S., Retailleau, P., and Ziessel, R., Synlett, 2007, vol. 19, p. 3027. https://doi.org/10.1055/s-2007-990965
Prokhorov, A.M., Slepukhin, P.A., Rusinov, V.L., Kalinin, V.N., and Kozhevnikov, D.N., Tetrahedron Lett., 2008, vol. 49, no. 23, p. 3785. https://doi.org/10.1016/j.tetlet.2008.04.008
Krinochkin, A.P., Reddy, G.M., Kopchuk, D.S., Slepukhin, P.A., Shtaitz, Y.K., Khalymbadzha, I.A., Kovalev, I.S., Kim, G.A., Ganebnykh, I.N., Zyryanov, G.V., Chupakhin, O.N., and Charushin, V.N., Mendeleev Commun., 2021, vol. 31, p. 542. https://doi.org/10.1016/j.mencom.2021.07.035
Rammohan, A., Krinochkin, A.P., Kopchuk, D.S., Shtaitz, Ya.K., Kovalev, I.S., Savchuk, M.I., Zyryanov, G.V., Rusinov, V.L., and Chupakhin, O.N., Russ. J. Org. Chem., 2022, vol. 58, no. 2, p. 175. https://doi.org/10.1134/S1070428022020026
Rammohan, A., Krinochkin, A.P., Kopchuk, D.S., Shtaitz, Ya.K., Savchuk, M.I., Starnovskaya, E.S., Zyryanov, G.V., Rusinov, V.L., and Chupakhin, O.N., Russ. J. Org. Chem., 2022, vol. 58, no. 2, p. 180. https://doi.org/10.1134/S1070428022020038
Borowicz, P., Grabowska, A., Leś, A., Kaczmarek, L., and Zagrodzki, B., Chem. Phys. Lett., 1998, vol. 291, p. 351. https://doi.org/10.1016/S0009-2614(98)00565-X
Mongin, F., Trécourt, F., Gervais, B., Mongin, O., and Quéguiner, G., J. Org. Chem., 2002, vol. 67, p. 3272. https://doi.org/10.1021/jo010913r
Izuta, S., Kosaka, S., Kawai, M., Miyano, R., Matsuo, H., Matsumoto, A., Nonaka, K., Takahashi, Y., Omura, S., and Nakashima, T., J. Antibiot., 2018, vol. 71, p. 535. https://doi.org/10.1038/s41429-018-0028-0
Kozhevnikov, D.N., Kozhevnikov, V.N., Kovalev, I.S., Rusinov, V.L., Chupakhin, O.N., and Aleksandrov, G.G., Russ. J. Org. Chem., 2002, vol. 38, no. 5, p. 744. https://doi.org/10.1023/A:1019631610505
Sandleben, A., Vogt, N., Hörner, G., and Klein, A., Organometallics, 2018, vol. 37, no. 19, p. 3332. https://doi.org/10.1021/acs.organomet.8b00559
SMART and SAINT-Plus. Versions 5.0. Data Collection and Processing Software for the SMART System. Madison: Bruker AXS Inc., 1998.
SHELXTL/PC. Versions 5.10. An Integrated System for Solving, Refining and Displaying Crystal Structures from Diffraction Data. Madison: Bruker AXS Inc., 1998.
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., and Puschmann, H., J. Appl. Cryst., 2009, vol. 42, p. 339. https://doi.org/10.1107/S0021889808042726
Krinochkin, A.P., Shtaitz, Ya.K., Rammohan, A., Butorin, I.I., Savchuk, M.I., Khalymbadzha, I.A., Kopchuk, D.S., Slepukhin, P.A., Melekhin, V.V., Shcheglova, A.V., Zyryanov, G.V., and Chupakhin, O.N., Eur. J. Org. Chem., 2022, vol. 22, Article e202200227. https://doi.org/10.1002/ejoc.202200227
Funding
The work was supported by the Council for Grants of the President of the Russian Federation (grant no. MK-320.2021.1.3), as well as within the framework of the governmental task (topic AAAA-A19-119011790132-7).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
No conflict of interest was declared by the authors.
Rights and permissions
About this article
Cite this article
Rammohan, A., Shtaitz, Y.K., Ladin, E.D. et al. Solvent-Free Reaction of 3,6-Diaryl-1,2,4-triazine-5-carbonitriles with 2-Amino-4-aryloxazoles. Russ J Gen Chem 93, 263–267 (2023). https://doi.org/10.1134/S1070363223020056
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363223020056