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mp 92–93°C. IR spectrum, ν, cm–1: 2622 (BH), 1769
Cl 19.68; N 3.89; S 8.90. M 360.21.
(C=O). Mass spectrum: m/z 617 [M]+. Found, %: C 50.95;
H 5.80; B 17.31. C26H36B10O10. Calculated, %: C 50.64;
H 5.88; B 17.53. M 616.67.
5-(1,3-Dioxan-2-yl)-2-methoxyphenyl 4,5-di-
chloroisothiazole-3-carboxylate (XLVI). Yield 82%,
mp 113–114°C. IR spectrum, ν, cm–1: 1746 (C=O).
Mass spectrum: m/z 389 [M]+. Found, %: C 46.51;
H 3.48; Cl 17.88; N 3.21; S 7.90. C15H13Cl2NO5S. Cal-
culated, %: C 46.17; H 3.36; Cl 18.17; N 3.59; S 8.22.
M 390.24.
Bis[4-(1,3-dioxan-2-yl)-2-ethoxyphenyl] [m-1-
(C),7-(C)-carboranyl]dimethanoate (LIV). Yield 80%,
mp 91–92°C. IR spectrum, ν, cm–1: 2620 (BH), 1770
(C=O). Mass spectrum: m/z 644 [M]+. Found, %: C 52.71;
H 6.38; B 16.20. C28H40B10O10. Calculated, %: C 52.16;
H 6.25; B 16.77. M 644.72.
4-(1,3-Dioxan-2-yl)-2-methoxyphenyl 4,5-dichlo-
roisothiazole-3-carboxylate (XLVII). Yield 84%,
mp 159–160°C. IR spectrum, ν, cm–1: 1757 (C=O).
Mass spectrum: m/z 389 [M]+. Found, %: C 46.59;
H 3.53; Cl 17.81; N 3.28; S 7.83. C15H13Cl2NO5S. Cal-
culated, %: C 46.17; H 3.36; Cl 18.17; N 3.59; S 8.22.
M 390.24.
3-Hydroxypropyl 4-(1,3-dioxan-2-yl)benzoate
20
(LV). Yield 89%, d 1.1174, nD20 1.5230. IR spectrum, ν,
20
cm–1: 1718 (C=O). Mass spectrum: m/z 266 [M]+. Found,
%: C 66.45; H 7.13. C14H18O5. Calculated, %: C 63.15;
H 6.81. M 266.29.
Esters LVI, LVII. To a solution of 0.01 mol of
phenol VIII and 0.01 mol of anhydrous triethylamine in
50 ml of anhydrous ethyl ether was added by portions at
stirring 0.01 mol of isoxazolecarboxylic acid chloride
LVIII, LIX. The reaction mixture was left standing for
24 h at 20–23°C, the separated precipitate was filtered
off, washed in succession with ether, water (3 × 200 ml),
the saturated water solution of NaHCO3 (3 × 200 ml), and
again with water (3 × 200 ml). Esters LVI, LVII were
dried in air at 25–30°C for 2–3 days.
4-(1,3-Dioxan-2-yl)-2-methoxyphenyl 4,5-dichlo-
roisothiazole-3-carboxylate (XLVIII). Yield 80%, mp
63–64°C. IR spectrum, ν, cm–1: 1756 (C=O). Mass spec-
trum: m/z 403 [M]+. Found, %: C 47.92; H 3.86; Cl 17.10;
N 3.07; S 7.58. C16H15Cl2NO5S. Calculated, %: C 47.54;
H 3.74; Cl 17.54; N 3.46; S 7.93. M 404.27.
4-(1,3-Dioxan-2-yl)-2-methoxyphenyl [m-(C)-carbo-
ranyl]methanoate (XLIX). Yield 82%, mp 93–94°C. IR
spectrum, ν, cm–1: 3062 (CHcarborane), 2608 (BH), 1769
(C=O). Mass spectrum: m/z 380 [M]+. Found, %: C 44.62;
H 6.50; B 28.00. C14H24B10O5. Calculated, %: C 44.20;
H 6.36; B 28.42. M 380.45.
4-(1,3-Dioxan-2-yl)-2-methoxyphenyl 5-phe-
nylisoxazole-3-carboxylate (LVI). Yield 88%, mp
75–76°C. IR spectrum, ν, cm–1: 1752 (C=O). Mass
spectrum: m/z 381 [M]+. Found, %: C 66.47; H 5.18;
N 3.29. C21H19NO6. Calculated, %: C 66.13; H 5.03;
N 3.67. M 381.38.
4-(1,3-Dioxan-2-yl)-2-ethoxyphenyl [m-(C)-car-
boranyl]methanoate (L). Yield 83%, mp 59–60°C. IR
spectrum, ν, cm-1: 3060 (CHcarborane.), 2609 (BH), 1768
(C=O). Mass spectrum: m/z 394 [M]+. Found, %: C 45.90;
H 6.73; B 27.05. C15H26B10O5. Calculated, %: C 45.67;
H 6.64; B 27.41. M 394.47.
4-(1,3-Dioxan-2-yl)-2-methoxyphenyl 5-(4-meth-
ylphenyl)isoxazole-3-carboxylate (LVII). Yield 89%,
mp 126–127°C. IR spectrum, ν, cm–1: 1767 (C=O). Mass
spectrum: m/z 395 [M]+. Found, %: C 67.16; H 5.57;
N 3.22. C22H21NO6. Calculated, %: C 66.83; H 5.35;
N 3.54. M 395.41
Bis[4-(1,3-dioxan-2-yl)phenyl] [m-1-(C),7-(C)-
carboranyl]dimethanoate (LI). Yield 81%, mp 121–
122°C. IR spectrum, ν, cm–1: 2615 (BH), 1757 (C=O).
Mass spectrum: m/z 557 [M]+. Found, %: C 52.10;
H 6.04; B 18.89. C24H32B10O8. Calculated, %: C 51.79;
H 5.79; B 19.42. M 556.62.
REFERENCES
1. Pershina, L.A. and Efanov, M.V., Khim. Rast. Syr’ya, 1997,
no. 2, p. 42; Potkin, V., Zubenko, Y., Bykovetz, A., and
Zolotar, R., Nat. Prod. Commun., 2009, vol. 4, p. 1205; Di-
kusar, E.A., Potkin, V.I., Kozlov, N.G., and Tlegenov, R.T.,
Vestsi Belarussian Akad. Nauk, Ser. Khim. Navuk, 2011,
vol. 4, p. 105; Govindasami, T., Pandey, A., Palanivelu,
N., and Pandey, A., Int. J. Org. Chem., 2011, vol. 1, p. 71;
Potkin, V.I., Gadzhily, R.A., Dikusar, E.A., Petkevich, S.K.,
Zhukovskaya, N.A., andAliev, A.G., Zh. Org. Khim., 2012,
Bis[5-(1,3-dioxan-2-yl)-2-methoxyphenyl] [m-1-
(C),7-(C)-carboranyl]dimethanoate (LII). Yield 82%,
mp 152–153°C. IR spectrum, ν, cm–1: 2619 (BH), 1762
(C=O). Mass spectrum: m/z 617 [M]+. Found, %: C 51.12;
H 6.05; B 17.03. C26H36B10O10. Calculated, %: C 50.64;
H 5.88; B 17.53. M 616.67.
Bis[4-(1,3-dioxan-2-yl)-2-methoxyphenyl] [m-1-
(C),7-(C)-carboranyl]dimethanoate (LIII). Yield 81%,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 2 2013