Molecules 2018, 23, 520
13 of 22
anhydrous Na2SO4, the mixture was filtered and the solvent was removed under reduced pressure.
Finally, the crudes were purified by column chromatography on silica gel using CHCl3:MeOH (40:1 v/v
)
as eluent.
(E)-1-(3-(Benzyl(naphthalen-1-ylmethyl)amino)prop-1-en-1-yl)pyrrolidin-2-one (16a). Following the strategy
1 for the formation of allylamines, the reaction of γ-aminoalcohol 15a (200 mg, 0.52 mmol) and AlCl3
(69 mg, 0.52 mmol) in 4.0 mL of ACN afforded product 16a as a yellow oil. Yield: 92% (177 mg). FT-IR
1
(film): 3058, 3030, 2925, 2798, 1702, 1660, 1408, 1364, 1334, 1119 cm−1. H-NMR
δ (ppm): 8.28–8.21
(m, 1H), 7.89–7.82 (m, 1H), 7.77 (d, J = 8.0 Hz, 1H), 7.56 (d, J = 6.8 Hz 1H), 7.53–7.46 (m, 2H), 7.46–7.41
(m, 1H), 7.37–7.28 (m, 4H), 7.27–7.21 (m, 1H), 7.02 (d, J = 14.4 Hz, 1H), 5.00 (dt, J = 7.2, 14.4 Hz, 1H),
4.04 (s, 2H), 3.66 (s, 2H), 3.41 (t, J = 7.2 Hz, 2H), 3.19 (d, J = 6.8 Hz, 2H), 2.46 (t, J = 8.2 Hz, 2H), 2.06 (tt,
J = 7.6, 7.6 Hz, 2H). 13C-NMR
δ (ppm): 173.0 (C=O), 139.7 (Cq), 135.2 (Cq), 133.8 (Cq), 132.4 (Cq), 129.0,
128.3, 128.1, 127.7, 127.3, 126.8, 126.2, 125.5, 125.5, 125.2, 124.8, 108.8, 58.4, 56.6, 54.1, 45.2, 31.2, 17.3.
Anal. Calcd. for C25H26N2O: C, 81.05; H, 7.07; N, 7.56. Found: C, 80.82; H, 7.25; N, 7.32.
(E)-1-(3-((4-Chlorobenzyl)(naphthalen-1-ylmethyl)amino)prop-1-en-1-yl)pyrrolidin-2-one (16b). Following
the strategy 1 for the formation of allylamines, the reaction of
and AlCl3 (68 mg, 0.51 mmol) in 4.0 mL of ACN afforded product 16b as a yellow oil. Yield: 85%
(176 mg). FT-IR (film): 3046, 2925, 2882, 2803, 1702, 1660, 1488, 1408, 1298, 1089 cm−1 1H-NMR
(ppm): 8.25–8.20 (m, 1H), 7.87–7.83 (m, 1H), 7.77 (d, J = 8.4 Hz, 1H), 7.54–7.46 (m, 3H), 7.44–7.39
γ-aminoalcohol 15b (215 mg, 0.51 mmol)
.
δ
(m, 1H), 7.24 (s, 4H), 7.01 (d, J = 14.4 Hz, 1H), 4.96 (dt, J = 7.2, 14.4 Hz, 1H), 4.00 (s, 2H), 3.58 (s, 2H),
3.43 (t, J = 7.2 Hz, 2H), 3.15 (d, J = 6.8 Hz, 2H), 2.48 (t, J = 8.4 Hz, 2H), 2.09 (tt, J = 8.0, 8.0 Hz, 2H).
13C-NMR
δ (ppm): 173.0 (C=O), 138.3 (Cq), 134.9 (Cq), 133.8 (Cq), 132.4 (Cq), 132.3 (Cq), 130.2, 128.4,
128.2, 127.8, 127.3, 126.3, 125.5, 125.5, 125.2, 124.7, 108.4, 57.6, 56.8, 54.3, 45.2, 31.2, 17.4. Anal. Calcd.
for C25H25ClN2O: C, 74.15; H, 6.22; N, 6.92. Found: C, 74.02; H, 6.50; N, 7.05.
(E)-1-(3-((Benzo[d][1,3]dioxol-5-ylmethyl)(naphthalen-1-ylmethyl)amino)prop-1-en-1-yl)pyrrolidin-2-one (16c).
Following the strategy 1 for the formation of allylamines, the reaction of γ-aminoalcohol 15c (216 mg,
0.50 mmol) and AlCl3 (68 mg, 0.51 mmol) in 4.0 mL of ACN afforded product 16c as a yellow oil.
Yield: 77% (159 mg). FT-IR (film): 3045, 2977, 2922, 2884, 2802, 1701, 1660, 1487, 1441, 1409, 1364, 1298,
1
1243, 1113, 1038 cm−1. H-NMR
δ
(ppm): 8.30–8.24 (m, 1H), 7.88–7.82 (m, 1H), 7.77 (d, J = 8.4 Hz, 1H),
7.57–7.46 (m, 3H), 7.43 (t, J = 7.6 Hz, 1H), 7.03 (d, J = 14.4 Hz, 1H), 6.86 (s, 1H), 6.80–6.71 (m, 2H), 5.92
(s, 2H, OCH2O), 5.00 (dt, J = 7.2, 14.4 Hz, 1H), 4.00 (s, 2H), 3.53 (s, 2H), 3.42 (t, J = 7.2 Hz, 2H), 3.16 (d,
J = 6.8 Hz, 2H), 2.46 (t, J = 8.0 Hz, 2H), 2.05 (tt, J = 7.6, 7.6 Hz, 2H). 13C-NMR
δ (ppm): 172.9 (C=O),
147.4 (Cq), 146.3 (Cq), 135.1 (Cq), 133.7 (Cq), 133.5 (Cq), 132.3 (Cq), 128.2, 127.6, 127.2, 126.1, 125.4
(2 × CH), 125.1, 124.7, 121.9, 109.2, 108.5, 107.7, 100.7, 57.9, 56.4, 53.8, 45.1, 31.1, 17.2. Anal. Calcd. for
C26H26N2O3: C, 75.34; H, 6.32; N, 6.76. Found: C, 75.48; H, 6.21; N, 6.83.
(E)-1-(3-((Naphthalen-1-ylmethyl)(napthalen-2-ylmethyl)amino)prop-1-en-1-yl)pyrrolidin-2-one
(16d).
Following the strategy 1 for the formation of allylamines, the reaction of -aminoalcohol 15d (237 mg,
γ
0.54 mmol) and AlCl3 (73 mg, 0.55 mmol) in 4.0 mL of ACN afforded product 16d as a yellow oil.
Yield: 68% (154 mg). FT-IR (film): 3045, 2927, 2882, 2800, 1701, 1660, 1509, 1409, 1363, 1299, 1261, 1224,
1
1115 cm−1. H-NMR
δ (ppm): 8.02 (d, J = 8.4 Hz, 2H), 7.83 (d, J = 8.0 Hz, 2H), 7.77 (d, J = 8.4 Hz,
2H), 7.51 (d, J = 6.8 Hz, 2H), 7.47–7.38 (m, 4H), 7.28–7.22 (m, 2H), 7.06 (d, J = 14.4 Hz, 1H), 5.04 (dt,
J = 7.2, 14.4 Hz, 1H), 4.04 (s, 4H), 3.42 (t, J = 7.2 Hz, 2H), 3.22 (d, J = 7.2 Hz, 2H), 2.47 (t, J = 8.0 Hz,
2H), 2.07 (tt, J = 7.6, 7.6 Hz, 2H). 13C-NMR
δ (ppm): 172.9 (C=O), 135.1 (Cq), 133.8 (Cq), 132.5 (Cq),
128.2, 127.9 (2 × CH), 126.4, 125.4, 125.3, 125.2, 125.1, 108.4, 57.2, 54.6, 45.2, 31.1, 17.4. Anal. Calcd.
For C29H28N2O: C, 82.82; H, 6.71; N, 6.66. Found: C, 82.90; H, 6.85; N, 6.48.
(E)-1-(3-((Naphthalen-1-ylmethyl)(3,4,5-trimethoxybenzyl)amino)prop-1-en-1-yl)pyrrolidin-2-one
(16e).
Following the strategy 1 for the formation of allylamines, the reaction of -aminoalcohol 15e (239 mg,
γ
0.50 mmol) and AlCl3 (68 mg, 0.51 mmol) in 4.0 mL of ACN afforded product 16e as a yellow oil.
Yield: 69% (159 mg). FT-IR (film): 3042, 2298, 2936, 2831, 1700, 1660, 1591, 1505, 1461, 1414, 1230, 1125,