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1488
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(general procedure). A solution of boronic acid 13a or
13b, 2 equiv of sodium azide, and 0.2 equiv of cop-
per(II) sulfate pentahydrate in methanol was stirred
until the initial compound disappeared (TLC). The
solvent was removed under reduced pressure, the dry
residue was treated with water and extracted with ethyl
acetate, the extract was dried over anhydrous sodium
sulfate and evaporated under reduced pressure, and
the product was isolated by silica gel column
chromatography.
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(2-Azido-4,5-dimethoxyphenyl)methanol (14a)
was synthesized from 600 mg (2.5 mmol) of 13a using
322 mg (4.96 mmol) of sodium azide, 122 mg
(0.5 mmol) of CuSO4·5H2O, and 10 mL of methanol.
The product was isolated using petroleum ether–ethyl
acetate (3 :1) as eluent. Yield 210 mg (40%), dark
9. Colombel, V. and Baudoin, O., J. Org. Chem., 2009,
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p. 4149.
1
brown crystals, mp 91°C. H NMR spectrum
11. Joncour, A., Décor, A., Liu, J.-M., Tran Huu Dau, M.-E.,
(400 MHz), δ, ppm: 3.79 s (3H, MeO), 3.84 s (3H,
MeO), 4.49 s (2H, CH2), 6.57 s (1H, CH), 6.84 s
(1H, CH). 13C NMR spectrum (101 MHz), δC, ppm:
14.08, 22.65, 56.12, 60.69, 101.81, 112.24, 129.42,
146.33, 149.28. Found, %: C 51.87; H 5.45; N 20.90;
O 21.78. C9H11N3O3. Calculated, %: C 51.67; H 5.30;
N 20.09; O 24.40.
and Baudoin, O., Chem. Eur. J., 2007, vol. 13, p. 5450.
12. Joncour, A., Liu, J.-M., Décor, A., Thoret, S.,
Wdzieczak-Bakala, J., Bignon, J., and Baudoin, O.,
ChemMedChem, 2008, vol. 3, p. 1731.
13. Chatterjee, N., Sarkar, S., Pal, R., and Sen, A.K.,
Tetrahedron Lett., 2014, vol. 55, p. 2261.
14. De Moliner, F., Bigatti, M., Banfi, L., Reva, R., and
(2-Azido-3,4,5-trimethoxyphenyl)methanol (14b)
was synthesized from 100 mg (0.41 mmol) of 13b
using 54 mg (0.82 mmol) of sodium azide, 20.5 mg
(0.082 mmol) of CuSO4·5H2O, and 3 mL of methanol.
The product was isolated using petroleum ether–ethyl
acetate (1 :1) as eluent. Yield 44 mg (45%), dark
Basso, A., Org. Lett., 2014, vol. 16, p. 2280.
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Chem., Int. Ed. Engl., 1994, vol. 33, p. 15.
1
17. Abal, M., Andreu, J.M., and Barasoain, I., Curr. Cancer
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brown oil. H NMR spectrum (400 MHz), δ, ppm:
3.84 s (3H, MeO), 3.87 s (3H, MeO), 3.96 s (3H,
MeO), 4.58 s (2H, CH2), 6.68 s (1H, CH). 13C NMR
spectrum (101 MHz), δC, ppm: 56.16, 60.95, 61.76,
62.00, 107.31, 123.44, 127.79, 142.16, 148.12, 150.63.
Found, %: C 50.19; H 5.68; N 17.47; O 26.66.
C10H13N3O4. Calculated, %: C 50.21; H 5.48; N 17.53;
O 26.78.
18. Zhang, L., Chen, X., Xue, P., Sun, H.H.Y.,
Williams, I.D., Sharpless, K.B., Fokin, V.V., and Jia, G.,
J. Am. Chem. Soc., 2005, vol. 127, p. 15998.
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Lett., 2007, vol. 9, p. 5337.
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Zhyao, H., Lin, Z., Jia, G., and Fokin, V., J. Am. Chem.
Soc., 2008, vol. 130, p. 8923.
This study was performed under financial support
by the Russian Foundation for Basic Research (project
no. 14-03-91342) and by the Ministry of Education
and Science of the Russian Federation (project
no. 4.619.2014/K).
21. Huisgen, R., Angew. Chem., Int. Ed. Engl., 1963, vol. 2,
p. 565.
22. Naumov, M.I., Sutirin, S.A., Shavyrin, A.S.,
Ganina, O.G., Beletskaya, I.P., Bourgarel-Rey, V.,
Combes, S., Finet, J.-P., and Fedorov, A.Yu., J. Org.
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 52 No. 10 2016