RODYGIN et al.
1434
absence of amine (as base) and were isolated by col-
umn chromatography on silica gel using methyl tert-
butyl ether–hexane (1:1) as eluent.
128.71, 130.04, 130.08, 130.55, 132.98, 156.35,
156.66. Found, %: C 66.50; H 5.72; N 12.80; O 4.96;
S 9.79. C18H19N3OS. Calculated, %: C 66.43; H 5.88;
N 12.91; O 4.92; S 9.85. ee = 7.0% (250×4.6-mm
Chiralcel OD-H column; hexane–propan-2-ol, 7:3;
flow rate 0.8 ml/min; UV detector, λ 254 nm).
3-Methylsulfinyl)-4,5-diphenyl-4H-1,2,4-triazole
(VII). Yield 87%, colorless crystals, mp 147–148°C,
[α]D25 = +35.3° (c = 0.51, EtOH). IR spectrum:
ν 1068 cm–1 (S=O). 1H NMR spectrum, δ, ppm: 3.30 s
3-Benzylsulfinyl-4,5-diphenyl-4H-1,2,4-triazole
(XI). Yield 89%, colorless crystals, mp 197–198°C. IR
13
(3H, CH3), 7.29–7.61 m (10H, Harom). C NMR spec-
1
spectrum: ν 1038 cm–1 (S=O). H NMR spectrum, δ,
trum, δC, ppm: 37.37, 125.58, 127.68, 128.68, 128.71,
130.03, 130.12, 130.55, 132.98, 156.35, 156.66.
Found, %: C 63.45; H 4.69; N 14.91; O 5.55; S 11.13.
C15H13N3OS. Calculated, %: C 63.58; H 4.62; N 14.83;
O 5.65; S 11.32. ee = 15% (250×4.6-mm Chiralcel
OD-H column; hexane–propan-2-ol, 7:3; flow rate
0.8 ml/min; UV detector, λ 219 nm).
ppm: 4.72 d (2H, CH2, AB system, J = 12.46 Hz),
7.02–7.45 m (15H, Harom). 13C NMR spectrum, δC,
ppm: 58.82, 125.64, 127.55, 128.61, 128.68, 128.76,
128.97, 129.91, 130.39, 130.49, 130.88, 132.90,
138.31, 155.99. Found, %: C 70.12; H 4.85; N 11.60;
O 4.35; S 9.00. C21H17N3OS. Calculated, %: C 70.17;
H 4.77; N 11.69; O 4.45; S 8.92. ee = 80%. (250×4.6-
mm Kromasil® 5-AmyCoat column; hexane–propan-
2-ol, 7:3; flow rate 1 ml/min; UV detector, λ 219 nm).
3-Ethylsulfinyl-4,5-diphenyl-4H-1,2,4-triazole
(VIII). Yield 80%, colorless crystals, mp 148–149°C,
[α]D25 = +17.0° (c = 0.41, EtOH). IR spectrum:
1
ν 1065 cm–1 (S=O). H NMR spectrum, δ, ppm: 1.44 t
The IR spectra were recorded from samples pre-
pared as KBr pellets on a Shimadzu Prestige 21 spec-
(3H, CH3, J = 7.92 Hz), 3.53–3.67 m (2H, CH2), 7.29–
7.61 m (10H, Harom). 13C NMR spectrum, δC, ppm:
7.22, 45.22, 125.58, 127.71, 128.68, 128.71, 130.02,
130.08, 130.55, 132.98, 156.35, 156.66. Found, %:
C 64.55; H 5.00; N 14.01; O 5.45; S 10.83.
C16H15N3OS. Calculated, %: C 64.62; H 5.08; N 14.13;
O 5.38; S 10.78. ee = 11.6% (250×4.6-mm Chiralpak
AD column; hexane–propan-2-ol, 7:3; flow rate
1.0 ml/min; UV detector, λ 254 nm).
1
13
trometer. The H and C NMR spectra were obtained
on a Bruker Avance-300 instrument at 300 and
75 MHz, respectively, using CDCl3 as solvent The
melting points were determined on a Gallenkamp-
Sanyo melting point apparatus. The elemental com-
positions were determined on an EA 1110 CHNS-O
automatic analyzer (CE Instruments). The optical rota-
tions were measured on a Kruss P3002RS polarimeter.
4,5-Diphenyl-3-propylsulfinyl-4H-1,2,4-triazole
(IX). Yield 72%, colorless crystals, mp 131–132°C,
[α]D25 = +7.70° (c = 0.35, EtOH). IR spectrum:
This study was performed under financial support
by the Russian Foundation for Basic Research (project
no. 10-03-00969) and by the Chemistry and Materials
Science Department of the Russian Academy of
Sciences (project no. 09-T-3-1015).
1
ν 1061 cm–1 (S=O). H NMR spectrum, δ, ppm: 1.14 t
(3H, CH3, J = 8.19 Hz), 1.81–2.00 m (2H, CH2), 3.43–
3.46 m and 3.61–3.78 m (1H each, CH2), 7.29–7.61 m
(10H, Harom). 13C NMR spectrum, δC, ppm: 13.21,
16.30, 53.07, 125.58, 127.71, 128.68, 128.71, 130.04,
130.08, 130.55, 132.98, 156.35, 156.66. Found, %:
C 65.55; H 5.62; N 13.40; O 5.11; S 10.23.
C17H17N3OS. Calculated, %: C 65.57; H 5.50; N 13.49;
O 5.14; S 10.30. ee = 5.5% (250×4.6-mm Chiralpak
AD column; hexane–propan-2-ol, 7:3; flow rate
1.0 ml/min; UV detector, λ 254 nm).
REFERENCES
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 9 2011