REACTIONS OF N-(POLYCHLOROETHYLIDENE)ARENE- ...
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N-[1-(1-Allyl-1H-indol-3-yl)-2,2,2-trichloroethyl]-
trifluoromethanesulfonamide (IVb) was obtained
from Schiff base IIa and 1.57 g of N-allylindole. Yield
N-[2,2,2-Trichloro-1-(1H-indol-3-yl)ethyl]tri-
fluoromethanesulfonamide (IVe). A solution of
1.17 g of indole (IIIe) in 5 ml of carbon tetrachloride
was added dropwise under stirring to a reaction mix-
ture containing Schiff base IIa, cooled to –5°C. The
mixture was allowed to warm up to room temperature,
and the solvent was evaporated under reduced pres-
sure. According to the NMR data, the residue, 4.00 g,
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4.01 g (92%), mp 145°C. H NMR spectrum
(DMSO-d6), δ, ppm: 4.82 d (1H, CH2, 3JHH = 17.1 Hz),
3
4.88 d (1H, NCH2, JHH = 4.4 Hz), 5.14 d (1H, CH=,
3JHH = 10.2 Hz), 5.57 s (1H, CHCCl3), 6.03 m (1H,
CH2=), 7.12 t (1H, 5-H), 7.18 t (1H, 5-H), 7.46 d (1H,
7-H), 7.75 m (2H, 2-H, 4-H), 11.03 br.s (1H, NH).
13C NMR spectrum, δC, ppm: 48.15 (NCH2), 65.97
(CHNH), 102.23 (CCl3), 107.80 (C3), 110.47 (C7),
116.35 (=CH2), 118.70 (C4), 120.15 (C5), 121.82 (C6),
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was a tarry mixture of products. H NMR spectrum
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(CDCl3), δ, ppm: 5.58 d (1H, CH, JHH = 9.5 Hz),
6.69 d (1H, NH, 3JHH = 9.5 Hz), 7.10–7.45 m (4H, 2-H,
5-H, 6-H, 7-H), 7.65 d (1H, 4-H), 8.38 s (1H, NH).
13C NMR spectrum, δC, ppm: 66.48 (CH), 101.27
(CCl3), 109.63 (C3), 111.61 (C7), 118.70 (C4), 120.86
127.16 (C3a), 129.46 (C2), 134.10 (CH=), 135.10
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(C7a), 114.35, 117.55, 120.76, 123.96 q (CF3, JCF
=
(C5), 122.96 (C6), 124.26 (C2), 126.34 (C3a), 135.14
322.5 Hz). Found, %: C 38.46; H 2.75; Cl 24.32;
N 6.45; S 7.39. C14H12Cl3F3N2O2S. Calculated, %:
C 38.60; H 2.78; Cl 24.41; N 6.43; S 7.36.
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(C7a), 114.30, 117.49, 120.68, 123.89 q (CF3, JCF
=
321.4 Hz).
N-[1-(1-Butyl-1H-indol-3-yl)-2,2,2-trichloro-
ethyl]-4-chlorobenzenesulfonamide (Va) was synthe-
sized from Schiff base IIb and 1.73 g of N-butylindole.
N-[1-(1-Benzyl-1H-indol-3-yl)-2,2,2-trichloro-
ethyl]trifluoromethanesulfonamide (IVc) was ob-
tained from Schiff base IIa and 2.07 g of N-benzyl-
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Yield 4.24 g (86%), mp 186–188°C. H NMR spec-
indole. Yield 4.71 g (97%), mp 178–180°C. H NMR
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trum (DMSO-d6), δ, ppm: 0.87 t (3H, CH3, JHH
=
spectrum (DMSO-d6), δ, ppm: 5.34 and 5.39 (1H each,
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7.3 Hz), 1.13 m (CH2), 1.56 m (CH2), 3.97 m (2H,
CH2), 5.33 s (1H, CH), 7.01 t (1H, 5-H), 7.09 t (1H,
6-H), 7.29 d (1H, 7-H), 7.41 s (1H, 2-H), 7.51 d (4-H),
6.97, 7.41 (4H, C6H4, AA′BB′ system), 8.90 s (1H,
NH). 13C NMR spectrum, δC, ppm: 14.02 (CH3), 19.80
(CH2), 32.09 (CH2), 45.73 (CH2), 65.91 (CH), 103.26
(CCl3), 108.03 (C3), 110.11 (C7), 118.85 (C4), 120.02
(C5), 121.81 (C6), 127.92 (C3a), 129.22 (C2), 135.08
(C7a), 128.55, 137.28, 139.41 (C6H4). Found, %:
C 48.52; H 4.02; Cl 28.47; N 5.69; S 6.44.
C20H20Cl4N2O2S. Calculated, %: C 48.60; H 4.08;
Cl 28.69; N 5.67; S 6.49.
CH2, AB system, JHH = 16.1 Hz), 5.50 d (1H, CH,
3JHH = 9.5 Hz), 7.00–7.28 m (8H, C6H5, 7-H, 5-H,
6-H), 7.67 m (1H, 4-H), 7.77 s (1H, 2-H), 10.42 d (1H,
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NH, JHH = 9.5 Hz). 13C NMR spectrum, δC, ppm:
49.92 (CH2), 66.00 (CHNH), 102.24 (CCl3), 108.64
(C3), 109.95 (C7), 118.63 (C4), 120.15 (C5), 121.96
(C6), 126.33, 127.42, 127.62 (C3a), 128.50, 129.56
(C2), 135.17 (C7a), 137.04, 114.41, 117.62, 120.82,
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123.02 q (CF3, JCF = 322.2 Hz). Found, %: C 44.39;
H 2.90; Cl 22.03; N 5.70; S 6.67. C18H14Cl3F3N2O2S.
Calculated, %: C 44.51; H 2.91; Cl 21.90; N 5.77;
S 6.60.
N-[1-(1-Allyl-1H-indol-3-yl)-2,2,2-trichloro-
ethyl]-4-chlorobenzenesulfonamide (Vb) was ob-
tained from Schiff base IIb and 1.57 g of N-allyl-
N-{2,2,2-Trichloro-1-[1-(4-nitrophenyl)-1H-in-
dol-3-yl]ethyl}trifluoromethanesulfonamide (IVd)
was obtained from Schiff base IIa and 2.38 g of
N-(4-nitrophenyl)indole. Yield 4.91 g (95%), mp 155–
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indole. Yield 3.91 g (82%), mp 187–190°C. H NMR
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spectrum (DMSO-d6), δ, ppm: 4.64 d (2H, NCH2,
157°C. H NMR spectrum (DMSO-d6), δ, ppm: 5.70 s
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3JHH = 4.0 Hz), 4.79 d (1H, CH2, JHH = 17.1 Hz),
(1H, CHCCl3), 7.27–7.35 m (2H, 5-H, 6-H), 7.75 d
(1H, 7-H), 7.98 d (1H, 4-H), 8.24 s (1H, 2-H), 7.88 and
8.47 (4H, C6H4, AA′BB′ system), 11.12 br.s (1H, NH).
13C NMR spectrum, δC, ppm: 65.44 (CH), 101.53
(CCl3), 110.98 (C3), 112.67 (C7), 118.32 (C4), 119.74
(C5), 122.08 (C6), 123.73, 125.73, 128.41 (C3a), 128.80
(C2), 133.99 (C7a), 143.76, 145.16, 114.30, 117.50,
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5.11 d (1H, CH=, JHH = 10.3 Hz), 5.34 s (1H,
CHCCl3), 5.84 m (1H, CH2=), 7.02 t (1H, 5-H), 7.09 t
(1H, 6-H), 7.25 d (1H, 7-H), 7.43 s (1H, 2-H), 7.52 d
(1H, 4-H), 7.02 and 7.41 (4H, C6H4, AA'BB′), 8.99 br.s
(1H, NH). 13C NMR spectrum, δC, ppm: 48.55 (NCH2),
65.87 (CHNH), 103.15 (CCl3), 108.53 (C3), 110.37
(C7), 117.33 (=CH2), 118.91 (C4), 120.21 (C5), 121.97
(C6), 127.95 (C3a), 128.55, 128.66, 129.32 (C2), 134.14
(CH=), 135.15 (C7a), 137.36, 139.42. Found, %:
C 47.61; H 3.35; Cl 29.48; N 5.88; S 6.62.
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120.70, 123.78 q (CF3, JCF = 322.2 Hz). Found, %:
C 39.37; H 2.15; Cl 20.45; N 8.15; S 6.18.
C17H11Cl3F3N3O4S. Calculated, %: C 39.52; H 2.15;
Cl 20.58; N 8.13; S 6.20.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 44 No. 1 2008