1110
SHABUNINA et al.
4
-(4-Methoxyphenyl)pyridine-2,6-dicarboxylic
9. Hale, R.L. and Solas, D.W., US Patent no. 4761481A,
988.
1
1
acid (1b). Yield 3.93 g (14.4 mmol, 48%). H NMR
spectrum (DMSO-d ), δ, ppm: 3.80 s (3H, OMe),
.05 m (2H, C H ), 7.75 m (2H, C H ), 8.43 s (2H,
-H, 5-H). Found, %: C 61.67; H 3.89; N 5.01.
1
0. Van Staveren, C.J., Aarts, V.M.L.J., Grootenhuis, P.D.J.,
Droppers, W.J.H., Van Eerden, J., Harkema, S., and
Reinhoudt, D.N., J. Am. Chem. Soc., 1988, vol. 110,
p. 8134.
6
7
3
6 4 6 4
C H NO . Calculated, %: C 61.54; H 4.06; N 5.13.
1
4
11
5
1
The H NMR spectra were recorded on a Bruker
Avance-400 spectrometer at 400 MHz using tetra-
methylsilane as internal standard. The mass spectra
11. Kuffner, F. and Straberger, F., Monatsh. Chem., 1957,
vol. 88, p. 793.
(
electrospray ionization) were recorded on a Bruker
12. Tse, M.K., Bhor, S., Klawonn, M., Anilkumar, G.,
Jiao, H., Döbler, C., Spannenberg, A., Mägerlein, W.,
Hugl, H., and Beller, M., Chem. Eur. J., 2006, vol. 12,
p. 1855.
Daltonics MicrOTOF-Q II instrument (Bremen,
Germany). Elemental analysis was performed with
a Perkin Elmer 2400 Series II CHN analyzer. Pyri-
dinium salt 5 was prepared according to the procedure
described in [30].
3. Park, T.-H., Cychosz, K.A., Wong-Foy, A.G., Dailly, A.,
and Matzger, A.J., Chem. Commun., 2011, vol. 47,
p. 1452.
FUNDING
4. Fan, K., Li, F., Wang, L., Daniel, Q., Gabrielsson, E.,
and Sun, L., Phys. Chem. Chem. Phys., 2014, vol. 16,
p. 25234.
This study was performed under financial support by the
Russian Science Foundation (project no. 18-73-10119).
CONFLICT OF INTEREST
The authors declare no conflict of interest.
REFERENCES
5. Zhou, L., Kawate, T., Liu, X., Kim, Y.B., Zhao, Y.,
Feng, G., Banerji, J., Nash, H., Whitehurst, C., Jindal, S.,
Siddiqui, A., Seed, B., and Wolfe, J.L., Bioorg. Med.
Chem., 2012, vol. 20, p. 750.
6. Xiong, R., Mara, D., Liu, J., Van Deun, R., and
Borbas, K.E., J. Am. Chem. Soc., 2018, vol. 140,
p. 10975.
7. Hunig, S., Groβ, J., and Schenk, W., Justus Liebigs Ann.
Chem., 1973, p. 324.
1
2
. Kopchuk, D.S., Chepchugov, N.V., Kim, G.A., Zyrya-
nov, G.V., Kovalev, I.S., Rusinov, V.L., and Chupa-
khin, O.N., Tetrahedron Lett., 2016, vol. 57, p. 296.
https://doi.org/10.1016/ j.tetlet.2015.12.006
. Kozhevnikov, V.N., Kozhevnikov, D.N., Shabuni-
na, O.V., Rusinov, V.L., and Chupakhin, O.N., Tetra-
hedron Lett., 2005, vol. 46, p. 1521.
. Pabst, G.R., Schmid, K., and Sauer, J., Tetrahedron Lett.,
18. Zhu, C., Bi, B., Ding, Y., Zhang, T., and Chen, Q.-Y.,
Tetrahedron, 2015, vol. 71, p. 9251.
3
4
5
998, vol. 39, p. 6691.
https://doi.org/10.1016/S0040-4039(98)01438-5
19. Chouthaiwale, P.V., Lapointe, S., and Tanaka, F., Hetero-
cycles, 2017, vol. 95, p. 587.
. Nakamura, T., Mizukami, S., Tanaka, M., and
Kikuchi, K., Chem. Asian J., 2013, vol. 8, p. 2685.
. Cui, Y., Zou, W., Song, R., Yu, J., Zhang, W., Yang, Y.,
and Qian, G., Chem. Commun., 2014, vol. 50, p. 719.
https://doi.org/10.3987/COM-16-S(S)27
20. Yi, Y., Zhao, M.-N., Ren, Z.-H., Wang, Y.-Y., and
Guan, Z.-H., Green Chem., 2017, vol. 19, p. 1023.
https://doi.org/10.1039/ C6GC03137D
21. Hong, F., Hollenback, D., Singer, J.W., and Klein, P.,
Bioorg. Med. Chem. Lett., 2005, vol. 15, p. 4703.
https://doi.org/10.1016/ j.bmcl.2005.07.055
6
7
. Hale, R.L. and Solas, D.W., US Patent no. 5032677A,
1
991.
2
2. Katritzky, A.R., Xiang Ou, Y., Ellison, J., and
Musumarra, G., J. Chem. Soc., Perkin Trans. 2, 1983,
p. 1421.
. Chen, A.Y., Thomas, P.W., Stewart, A.C., Bergstrom, A.,
Cheng, Z., Miller, C., Bethel, C.R., Marshall, S.H.,
Credille, C.V., Riley, C.L., Page, R.C., Bonomo, R.A.,
Crowder, M.W., Tierney, D.L., Fast, W., and Cohen, S.M.,
J. Med. Chem., 2017, vol. 60, p. 7267.
23. Chouthaiwale, P.V. and Tanaka, F., Int. Patent Appl. Pub.
no. WO2016038890 A1, 2016.
https://doi.org/10.1021/ acs.jmedchem.7b00407
8
. Weller, D.D., Luellen, G.R., and Weller, D.L., J. Org.
Chem., 1982, vol. 47, p. 4803.
24. Chouthaiwale, P.V. and Tanaka, F., Chem. Commun.,
2014, vol. 50, p. 14881.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 6 2020