Beilstein J. Org. Chem. 2015, 11, 1000–1007.
EtOH affording thieno[2,3-b]indoles 12 as white to yellow
Supporting Information
needles.
Supporting Information File 1
Analytical data and copies of the 1H and 13C NMR spectra
of the new compounds.
8-Ethyl-2-phenyl-8H-thieno[2,3-b]indole (12a): Pale yellow
needles; Yield 500 mg (90%); mp 82–83 °C; 1H NMR
(500 MHz, CDCl3) δ 7.81 (d, J = 7.8 Hz, 1H), 7.67–7.57 (m,
3H), 7.42–7.33 (m, 3H), 7.30–7.26 (m, 1H), 7.25–7.21 (m, 1H),
7.21–7.16 (m, 1H), 4.28 (q, J = 7.3 Hz, 2H), 1.52 (t, J = 7.3 Hz,
3H); 1H NMR (500 MHz, DMSO-d6) δ 7.92 (s, 1H), 7.82 (d,
J = 7.7 Hz, 1H), 7.66 (d, J = 7.3 Hz, 2H), 7.58 (d, J = 8.2 Hz,
1H), 7.44–7.36 (m, 2H), 7.28–7.21 (m, 2H), 7.19–7.11 (m, 1H),
4.34 (q, J = 7.2 Hz, 2H), 1.40 (t, J = 7.2 Hz, 3H); 13C NMR
(126 MHz, DMSO-d6) δ 141.6, 140.8, 135.0, 134.8, 129.1,
126.7, 124.5, 123.4, 122.0, 121.5, 119.4, 119.1, 114.8, 109.9,
40.3, 13.6; IR(DRA): 474, 550, 567, 688, 746, 779, 835, 850,
905, 935, 999, 1015, 1049, 1078, 1100, 1131, 1162, 1191, 1207,
1252, 1330, 1350, 1377, 1393, 1409, 1439, 1477, 1496, 1524,
1595, 1671, 1734, 1776, 1867, 1894, 1942, 2888, 2928, 2972,
3029, 3053, 3748 cm−1; MS (+APCI): Calcd. for C18H15NS m/z
278.0998 [M + H], found m/z 278.1000 [M + H]; Crystal data
for 12a: Colorless crystals 0.24 × 0.19 × 0.13 mm,
θ < 25.6080°, 11563 reflections were collected, 7249 inde-
pendent reflections (Rint 0.0245), completeness 100%. Crystal is
monoclinic, space group Cc, a = 19.0695(13) Å,
b = 30.6399(16) Å, c = 7.8360(4) Å, α = 90.00°,
β = 106.777(6)°, γ = 90.00°, μ = 0.210 mm−1. The SHELXTL
program [35] was used for solution and structure refinement.
Refinement and the final R indices: R1 = 0.0432 [I>2σ(I)],
wR2 = 0.1050 [I>2σ(I)], R1 = 0.0772 (all data), wR2 = 0.1355
(all data), S = 1.004. Deposition number CCDC 1054153
contains the supplementary crystallographic data for this
structure. These data can be obtained free of charge from
the Cambridge Crystallographic Data Centre via http://
Acknowledgements
This work was supported by the Russian Foundation for Basic
Research (research projects No. 13-03-12434-ofi_m2, 13-03-
96049-r_ural_a, 14-03-01017_A, 15-03-00924_А) and the
Scientific Council of the President of the Russian Federation
(grant МК-3043.2014.3).
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8-Ethyl-2-(2-nitrophenyl)-8H-thieno[2,3-
b]indole (12f)
Yellow powder; Yield 530 mg (82%); mp 103–104 °C;
1H NMR (400 MHz, DMSO-d6) δ 7.94 (d, J = 7.8 Hz, 1H),
7.87 (d, J = 7.8 Hz, 1H), 7.77–7.71 (m, 2H), 7.67–7.53 (m, 3H),
7.33–7.27 (m, 1H), 7.22–7.13 (m, 1H), 4.37 (q, J = 7.2 Hz, 2H),
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148.9, 143.0, 140.8, 132.5, 131.7, 128.6, 127.6, 127.0, 123.9,
123.3, 122.4, 121.3, 119.6, 119.4, 118.7, 110.0, 40.4, 13.5;
IR(DRA): 482, 549, 567, 584, 646, 662, 685, 700, 738, 746,
770, 834, 845, 861, 919, 941, 953, 986, 1015, 1052, 1084, 1134,
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3075, 3058 cm−1; Anal. calcd for C18H14N2O2S: C, 67.06; H,
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