SYNTHESIS OF PYRROLE N-DERIVATIVES FROM OXAZOLIDINES
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1
%: C 72.97; H 10.51; N 7.66. C11H19NO. Calculated, %:
C 72.88; H 10.56; N 7.73.
1650, 1500 (C=C). Н NMR spectrum, δ, ppm: 1.13 t
(3H, Me, 3J 6.0 Hz), 1.30–1.95 m [10H, (CH2)5], 2.42 q
3
(2H, MeCH2, J 6.0 Hz), 3.60 m (1H, NCH), 5.75 m
2-Butyl-1-(2-hydroxyethyl)-3-propylpyrrole (IIe).
Yield 11.09 g (53%) (а), bp 125–127°С (2 mm Hg),
d420 0.9479, nD20 1.4965. IR spectrum, ν, cm–1: 3441 (OH),
(1H, Н4), 6.30 s (1H, Н2), 6.42 m (1H, Н5). Found, %:
C 81.20; H 10.96; N 7.78. C12H19N. Calculated, %:
C 81.30; H 10.80; N 7.90.
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3093 (=CH), 1657, 1490, 1465, 1377 (C=C). Н NMR
spectrum, δ, ppm: 0.91 t (3H, CH2CH2CH2Me, 3J 7.2 Hz),
1-Butyl-3-isopropylpyrrole (IIj). Yield 12.06 g
(73%) (а), bp 68–70°С(3 mm Hg), d420 0.8642, nD20 1.4705
{bp 66–68°С (2.7 mm Hg), d420 0.8639, nD20 1.4701 [5]}.
IR spectrum, ν, cm–1: 3120 (OH), 3110 (=CH), 1650,
1500 (C=C). 1Н NMR spectrum, δ, ppm: 0.87 t (3H, Me,
3J 7.0 Hz), 0.96–1.59 m (4H, CH2CH2Me), 1.14 d (6H,
3
0.94 t (3H, CH2CH2Me, J 7.4 Hz), 1.32–1.56 m (6H,
CH2CH2Me, CH2CH2CH2Me), 2.02 br.s (1H, OH), 2.32 t
(2H, CH2CH2Me, 3J 7.7 Hz), 2.50 t (2H, CH2CH2CH2Me,
3
3J 7.5 Hz), 3.76 t (2H, NCH2, J 5.5 Hz), 3.90 t (2H,
3
3
CH2O, J 5.5 Hz), 5.96 d (1H, Н4, J 2.6 Hz), 6.53 d
(1H, Н5, 3J 2.6 Hz). Found, %: C 74.46; H 11.15; N 6.54.
C13H23NO. Calculated, %: C 74.59; H 11.07; N 6.69.
3
CHMe2, J 6.9 Hz), 2.67 m (1H, CHMe2), 3.65 t (2H,
NCH2, J 7.0 Hz), 5.80 m (1H, Н4), 6.23 s (1H, Н2),
3
6.31 m (1H, Н5). Found, %: C 80.07; H 11.43; N 8.34.
1-(2-Hydroxyethyl)-3-octylpyrrole (IIf). Yield
11.84 g (53%) (а), bp 99–101°С (3 mm Hg), d420 0.9380,
nD20 1.5050. IR spectrum, ν, cm–1: 3400 (OH), 3110
(=CH), 1650, 1494 (C=C). 1Н NMR spectrum, δ, ppm:
0.84 t (3H, Me, 3J 6.0 Hz), 1.21–1.38 m [12H, (CH2)6],
2.35 t (2H, C3CH2, 3J 7.0 Hz), 3.20 br.s (1H, OH), 3.79 t
C11H19N. Calculated, %: C 79.94; H 11.59; N 8.47.
1-(2-Hydroxypropyl)-4-methyl-2-phenylpyrrole
(IIk). Yield 7.10 g (33%) (а), bp 163–165°С (5 mm Hg),
d420 1.0421, nD20 1.5731. IR spectrum, ν, cm–1: 3410
(OH), 3105 (=СH), 1660, 1585, 1490 (C=C). Н NMR
spectrum, δ, ppm: 1.20 d (3H, Me, J 5.4 Hz), 2.03 s
(3H, С4Me), 3.57–3.74 m (2H, NCH2CHOH), 3.96 m
(2H, NCH2CHOH), 6.03 s (1H, Н3), 6.57 m (1H, Н5),
7.26–7.34 m (5H, Ph). Found, %: C 78.23; H 8.06; N 6.60.
C14H17NO. Calculated, %: C 78.10; H 7.96; N 6.51.
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3
3
3
(2H, NCH2, J 5.5 Hz), 3.91 t (2H, CH2O, J 5.5 Hz),
5.79 m (1H, Н4), 6.26 s (1H, Н2), 6.36 m (1H, Н5).
Found, %: C 75.33; H 11.37; N 6.20. C14H25NO. Calcu-
lated, %: C75.28; H 11.28; N 6.27.
1-(2-Hydroxyethyl)-5,6,7,8-tetrahydrocyclo-
hepta(b)pyrrole (IIg). Yield 13.62 g (76%) (а), 8.25 g
(46%) (b), bp 140–142°С (3 mm Hg), d420 1.0651,
nD20 1.5410 {bp 138–140°С (4 mm Hg), d420 1.0652,
nD20 1.5408 [5]}. IR spectrum, ν, cm–1: 3436 (OH), 3118
(=CH), 1486, 1443, 1372 (C=C). 1Н NMR spectrum, δ,
ppm: 1.72–1.74 m (4H, C5H2, C6H2), 1.85–1.88 m (2Н,
C7H2), 2.61–2.64 m (2Н, C8H2), 2.68–2.74 m (3Н, OH,
C4H2), 3.73 t (2H, NCH2, 3J 5.5 Hz), 3.96 t (2H, CH2O,
1-(2-Hydroxyethyl)-4,5,6,7-tetrahydroindole (IIl).
Yield 7.27 g (44%) (b), bp 134–136°С (3 mm Hg),
d420 1.0803, nD20 1.5418. {bp 136–138°С (4 mm Hg),
d420 1.0800, nD20 1.5400 [8]}. IR spectrum, ν, cm–1: 3433
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(OH), 3092 (=СH), 1576, 1487, 1367 (C=C). Н NMR
spectrum, δ, ppm: 1.73–1.79 m (2H, C5H2), 1.83–1.89 m
(2Н, C6H2), 2.09 br.s (1H, OH), 2.55 m (4H, С4Н2,
С7Н2), 3.79 t (2H, NCH2, 3J 5.5 Hz), 3.91 t (2H, CH2O,
3J 5.5 Hz), 5.98 d (1Н, Н3, J 2.7 Hz), 6.59 d (1Н, Н2,
3J 2.7 Hz). Found, %: C 72.63; H 9.20; N 8.42. C10H15NO.
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3
3J 5.5 Hz), 5.94 d (1Н, Н3, J 2.4 Hz), 6.48 d (1Н, Н2,
3J 2.4 Hz). Found, %: C 73.61; H 9.60; N 7.76. C11H17NO.
Calculated, %: C 72.69; H 9.15; N 8.48.
Calculated, %: C 73.70; H 9.56; N 7.81.
1-(2-Hydroxyethyl)-2-methyl-3-propylpyrrole
(V) and 2-butyl-1-(2-hydroxyethyl)pyrrole (VI).
Yield 10.20 g (61%) (а), bp 117–119°С (4 mm Hg),
d420 0.9685, nD20 1.5016. IR spectrum, ν, cm–1: 3450 (OH),
3100 (=CH), 1670, 1495 (=CH). 1Н NMR spectrum, δ,
ppm: 0.92–0.99 m (3H, 2MeCH2), 1.41–1.68 m [3H,
Me(CH2)2CH2, MeCH2CH2], 2.15 s (1.5H, MeC2), 2.37 t
(1H, MeCH2CH2, 3J 7.8 Hz), 2.58 t [1H, Me(CH2)2CH2,
3J 7.6 Hz], 3.21 br.s (1H, OH), 3.76–3.81 m (2H, CH2O),
3.92–3.98 m (2H, NCH2) 5.84 m [0.5H, Н3 (VI)],
5.91 d [0.5H, H4 (V), 3J 2.7 Hz], 6.02 t [0.5H, H4 (VI),
3J 3.1 Hz], 6.50 d [0.5H, H5 (V), 3J 2.7 Hz], 6.56 m [0.5H,
1-(2-Hydroxyethyl)-2-phenylpyrrole (IIh). Yield
6.37 g (34%) (а), 4.11 g (22%) (b), bp 142–143°С
(2 mm Hg), d420 1.1129, nD20 1.6021. IR spectrum, ν, cm–1:
3391 (OH), 3101, 3060, 3028 (=CH), 1651, 1602, 1493,
1472 (C=C). 1Н NMR spectrum, δ, ppm: 2.13 br.s (1H,
3
OH), 3.61 t (2H, NCH2, J 5.5 Hz), 3.99 t (2H, CH2O,
3J 5.5 Hz), 6.16–6.19 m (2Н, Н3, Н4), 6.77 m (1Н, Н5),
7.24–7.35 m (5H, Ph). Found, %: C 77.00; H 6.95; N 7.34.
C12H13NO. Calculated, %: C 76.98; H 7.00; N 7.48
1-Cyclohexyl-3-ethylpyrrole (IIi). Yield 10.64 g
(60%) (а), bp 156–157°С (2 mm Hg), d420 0.9282,
nD20 1.4869. IR spectrum, ν, cm–1: 3110, 3090 (=CH),
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 50 No. 2 2014