Chemistry of Heterocyclic Compounds 2017, 53(5), 526–531
(1H, dd, J = 2.3, J = 1.8, H-2 pyrrole); 7.42–7.36 (2H, m,
J = 7.8, J = 7.7, H-3,5 Ph); 7.17 (1H, dd, J = 2.3, J = 1.9,
H-2 pyrrole); 7.13 (1H, dd, J = 7.8, J = 1.3, H-4 Ph); 6.89
(1H, dd, J = 2.9, J = 2.3, H-5 pyrrole); 6.46 (1H, dd,
J = 2.9, J = 1.9, H-4 pyrrole); 2.22 (3H, s, 3CH
adamantane); 2.12–2.10 (6H, m) and 1.79–1.71 (6H, m, 6CH2
adamantane). 13C NMR spectrum, δ, ppm: 136.3 (Cquat);
128.5 (2C, CH); 125.0 (CH); 124.8 (2C, CH); 123.7 (Cquat);
117.5 (CH); 113.5 (CH); 105.3 (CH); 55.2 (Cquat); 43.8
(CH2); 36.2 (CH2); 29.6 (CH). Mass spectrum, m/z (Irel, %):
277 [M]+ (100).
H-3',5' Ph); 7.33–7.27 (1H, m, H-4 Ph); 7.24–7.19 (1H, m,
H-4' Ph); 7.15 (1H, dd, J = 3.0, J = 2.3, H-5 pyrrole); 6.70
(1H, dd, J = 3.0, J = 1.8, H-4 pyrrole). 13C NMR spectrum,
δ, ppm: 140.6 (Cquat); 135.3 (Cquat); 129.6 (2C, CH); 128.7
(2C, CH); 126.8 (Cquat); 125.8 (2CH); 125.2 (2C, CH);
120.3 (2C, CH); 120.3 (CH); 115.8 (CH); 108.7 (CH).
(S)-3-Phenyl-1-(1-phenylethyl)-1H-pyrrole (11) was
obtained in the reaction of 3-phenylpent-4-enal (5) (0.20 g,
1.2 mmol) and (S)-1-phenylethanamine (0.15 g, 1.2 mmol).
Reaction time of the second stage was 15 h. Crude product
was purified by column chromatography (hexane–acetone,
99:1). Yield 0.23 g (75%), colorless oil. IR spectrum,
ν, cm−1: 3058, 2978–2933, 1603–1493, 1949–1806, 1447,
1-[1-(Prop-2-yn-1-yl)-4,5,6,7-tetrahydro-1H-indol-
5-yl]-ethan-1-one (14) was obtained in the reaction of
2-[(5S)-2-methylene-5-(prop-1-en-2-yl)cyclohexyl]acet-
aldehyde (6) (0.20 g, 1.1 mmol) and prop-2-ynamine (0.06 g,
1.1 mmol). Reaction time of the second stage was 10 h.
Crude product was purified by column chromatography
(hexane–acetone, 99:1). Yield 0.18 g (80%), yellow oil.
IR spectrum, ν, cm−1: 3060, 2996–2892, 1698, 1611, 1567,
1
1353, 749–630. H NMR spectrum, δ, ppm (J, Hz): 7.50
(2H, dd, J = 7.3, J = 2.0, H-2',6' Ph); 7.31 (2H, dd, J = 7.5,
J = 7.3, H-3',5' Ph); 7.30 (2H, dd, J = 7.7, J = 7.3, H-3,5 Ph);
7.25 (1H, dd, J = 7.3, J = 1.7, H-4 Ph); 7.14 (2H, dd,
J = 7.7, J = 1.7, H-2,6 Ph); 7.14 (1H, dd, J = 7.5, J = 2.0,
H-4' Ph); 7.05 (1H, dd, J = 2.4, J = 1.8, H-2 pyrrole); 6.76
(1H, dd, J = 2.8, J = 2.4, H-5 pyrrole); 6.49 (1H, dd,
J = 2.8, J = 1.8, H-3 pyrrole); 5.27 (1H, q, J = 7.1,
CHCH3); 1.86 (3H, d, J = 7.1, CH3). 13C NMR spectrum,
δ, ppm: 143.2 (Cquat); 135.9 (Cquat); 128.7 (2C, CH); 128.5
(2C, CH); 127.5 (CH); 125.9 (2C, CH); 125.2 (CH); 124.9
(2C, CH); 124.7 (Cquat); 120.6 (CH); 116.4 (CH); 106.2
(CH); 58.3 (CH); 22.1 (CH3). Mass spectrum, m/z (Irel, %):
247 [M]+ (100).
1
1395. H NMR spectrum, δ, ppm (J, Hz): 6.64 (1H, d,
J = 2.8, H-2); 5.98 (1H, d, J = 2.8, H-3); 4.52 (2H, d,
J = 2.6, NCH2); 2.79 (1H, ddd, J = 13.2, J = 5.4, J = 1.0,
4-CH2); 2.69 (1H, ddd, J = 13.2, J = 5.9, J = 3.0) and 2.68
(1H, dddd, J = 13.2, J = 11.2, J = 6.0, J = 1.0, 7-CH2); 2.64
(1H, ddddd, J = 10.9, J = 10.8, J = 5.5, J = 5.4, J = 1.0,
5-CH); 2.59 (1H, dd, J = 13.2, J = 10.7, 4-CH2); 2.36 (1H,
t, J = 2.6, CH2CCH); 2.22 (3H, s, CH3); 2.18 (1H, ddddd,
J = 13.2, J = 6.0, J = 5.5, J = 3.0, J = 1.0) and 1.82 (1H, dddd,
J = 13.2, J = 11.2, J = 10.9, J = 5.9, 6-CH2). 13C NMR
spectrum, δ, ppm: 211.4 (Cquat); 126.9 (Cquat); 119.3 (CH);
116.4 (Cquat); 106.9 (CH); 78.3 (Cquat); 73.1 (CH); 48.5 (CH);
35.8 (CH2); 28.2 (CH3); 25.7 (CH2); 25.0 (CH2); 20.9
(CH2). Mass spectrum, m/z (Irel, %): 201 [M]+ (100).
(S)-3-Phenyl-2-(3-phenyl-1H-pyrrol-1-yl)propanoic acid
(12) was obtained in the reaction of 3-phenylpent-4-enal (5)
(0.2 g, 1.2 mmol) and L-phenylalanine (0.2 g, 1.2 mmol).
Reaction time of the second stage was 10 h. Crude product
was purified by column chromatography (hexane–acetone,
99:1). Yield 0.26 g (70%), white solid, mp 120°C (decomp).
IR spectrum, ν, cm−1: 3318, 3058, 2963–2933, 1939–1825,
1-[1-(S)-(1-Phenylethyl)-4,5,6,7-tetrahydro-1H-indol-
5-yl]ethan-1-one (15) was obtained in the reaction of
2-[(5S)-2-methylene-5-(prop-1-en-2-yl)cyclohexyl]acet-
aldehyde (6) (0.20 g, 1.10 mmol) and (S)-1-phenylethan-
1-amine (0.14 g, 1.12 mmol). Reaction time of the second
stage was 16 h. Crude product was purified by column
chromatography (hexane–acetone, 99:1). Yield 0.22 g (75%),
yellow oil. IR spectrum, ν, cm−1: 3088, 2977–2922, 1955–
1807, 1705, 1493–1450, 1355, 760–697. 1H NMR spectrum,
δ, ppm (J, Hz): 7.28 (2H, dd, J = 7.4, J = 7.3, H-3,5 Ph);
7.22 (1H, dd, J = 7.3, J = 1.4, H-4 Ph); 6.98 (2H, dd,
J = 7.4, J = 1.4, H-2,6 Ph); 6.78 (1H, d, J = 2.9, H-2); 6.02
(1H, d, J = 2.9, H-3); 5.18 (1H, q, J = 7.1, CH3CH); 2.86–
2.75 (1H, m, 5-CH); 2.67–2.55 (4H, m, 4,7-CH2); 2.18
(3H, s, CH3CH); 2.15–2.10 (1H, m, 6-CHeq); 1.78 (3H, d,
J = 7.1, CH3CO); 1.75–1.68 (1H, m, 6-CHax).13C NMR
spectrum, δ, ppm: 211.6 (Cquat); 143.7 (Cquat); 128.6 (2C,
CH); 127.4 (Cquat); 127.1 (CH); 125.6 (2C, CH); 116.6
(CH); 116.0 (Cquat); 106.0 (CH); 54.9 (CH); 48.7 (CH);
28.2 (CH3); 25.8 (CH2); 25.1 (CH2); 22.2 (CH3); 21.5
(CH2). Mass spectrum, m/z (Irel, %): 267 [M]+ (100).
1
1742, 1603–1504, 1412, 1362, 752–690. H NMR spectrum,
δ, ppm (J, Hz): 7.48 (2H, dd, J = 8.0, J = 2.1, H-2',6' Ph);
7.31 (2H, dd, J = 8.0, J = 7.7, H-3',5' Ph); 7.23 (2H, dd,
J = 7.5, J = 7.3, H-3,5 Ph); 7.22 (1H, dd, J = 7.3, J = 1.8,
H-4 Ph); 7.20 (1H, dd, J = 7.7, J = 2.1, H-4' Ph); 7.06 (2H,
dd, J = 7.5, J = 1.8, H-2,6 Ph); 7.02 (1H, dd, J = 2.5,
J = 2.0, H-2 pyrrole); 6.71 (1H, dd, J = 2.8, J = 2.5, H-5
pyrrole); 6.47 (1H, dd, J = 2.8, J = 2.0, H-4 pyrrole); 4.79
(1H, dd, J = 9.1, J = 5.9, CHCH2); 3.48 (1H, dd, J = 14.0,
J = 5.9) and 3.33 (1H, dd, J = 14.0, J = 9.2, CHCH2).
13C NMR spectrum, δ, ppm: 137.0 (Cquat); 136.0 (Cquat);
135.5 (Cquat); 128.9 (2C, CH); 128.7 (2C, CH); 128.6 (2C,
CH); 127.2 (CH); 127.0 (Cquat); 125.5 (CH); 125.1 (2C,
CH); 121.4 (CH); 116.8 (CH); 107.1 (CH); 63.5 (CH); 39.1
(CH2). Mass spectrum, m/z (Irel, %): 291 [M]+ (100).
1-(Adamantan-1-yl)-3-phenyl-1H-pyrrole (13) was
obtained in the reaction of 3-phenylpent-4-enal (5) (0.20 g,
1.2 mmol) and adamantan-1-amine (0.19 g, 1.2 mmol).
Reaction time of the second stage was 9 h. Crude product
was purified by column chromatography (hexane–acetone,
85:15). Yield 0.28 g (80%), white solid, mp 80°C (decomp.).
IR spectrum, ν, cm−1: 3053, 2922–2847, 1865–1741, 1603–
1-(1-Cyclopropyl-4,5,6,7-tetrahydro-1H-indol-5-yl)-
ethan-1-one (16) was obtained in the reaction of
2-[(5S)-2-methylene-5-(prop-1-en-2-yl)cyclohexyl]acet-
aldehyde (6) (0.20 g, 1.10 mmol) and cyclopropanamine
(0.06 g, 1.12 mmol). Reaction time of the second stage was
10 h. Crude product was purified by column chromato-
1
1549, 1445, 744–670. H NMR spectrum, δ, ppm (J, Hz):
7.51 (2H, dd, J = 7.8, J = 1.3, H-2,6 Ph); 7.30 (2H, dd,
530