10.1002/ejoc.201801155
European Journal of Organic Chemistry
FULL PAPER
7.29–7.16 (m, 3H), 6.96 (t, J = 8.7 Hz, 2H), 6.62 (m, 2H), 3.23 (t, J = 7.6
Hz, 2H), 3.00 (t, J = 7.7 Hz, 2H) ppm. 13C NMR (100 MHz, CDCl3): δ =
201.4, 161.5 (d, J = 243.7 Hz), 150.4, 137.2 (d, J = 3.2 Hz), 134.5, 131.1,
129.9 (d, J = 7.8 Hz), 118.0, 117.6, 116.0, 115.3 (d, J = 21.1 Hz), 41.1,
29.8 ppm. 19F NMR (376 MHz, CDCl3): δ = -118.37 ppm. HRMS (ESI):
calcd. for C15H14FNO ([M+H]): 244.1132, found: 244.1119. IR (KBr): ʋ (cm-
1) = 3475, 3348, 3240, 3038, 2927, 1651, 1614, 1548, 1450, 1157, 830,
753, 652.
2H), 3.06 (t, J = 7.5 Hz, 2H) ppm. 13C NMR (100 MHz, CDCl3): δ = 199.8,
148.3, 141.5, 138.9, 138.0, 129.5, 128.9, 128.6, 128.5, 127.6, 127.5, 126.2,
117.7, 111.9, 48.4, 40.6, 30.4 ppm. HRMS (ESI): calcd. for C22H21NO
([M+H]): 316.1696, found: 316.1714. IR (KBr): ʋ (cm-1) = 3408, 1667, 1602,
1491, 1341, 1180, 901, 763, 697.
1-(3-aminophenyl)-3-phenylpropan-1-one (Table 2, compound 2h)[new]
:
Prepared from 3’-aminoacetophenone (0.14g, 1.0 mmol) and benzyl
alcohol (0.22g, 2.0 mmol). After purification by column chromatography,
the compound was isolated as a white solid (0.21g, 0.9 mmol, 91%). Mp =
91–92 C. 1H NMR (400 MHz, CDCl3): δ = 7.36–7.20 (m, 8H), 6.90 (dd, J
= 7.9, 3.1 Hz, 1H), 4.14 (br, 2H), 3.26 (t, J = 7.6 Hz, 2H), 3.06 (t, J = 7.6
Hz, 2H) ppm. 13C NMR (100 MHz, CDCl3): δ = 199.6, 146.3, 141.4, 138.0,
129.6, 128.6, 128.5, 126.2, 120.0, 118.9, 114.4, 40.6, 30.3 ppm. HRMS
(ESI): calcd. for C15H15NO ([M+H]): 226.1226, found: 226.1228. IR (KBr):
ʋ (cm-1) = 3460, 3367, 1679, 1560, 1454, 1316, 1175, 773.
1-(2-aminophenyl)-3-(benzo[d][1,3]dioxol-5-yl)propan-1-one (Table 2,
compound 2c)[25]: Prepared from 2’-aminoacetophenone (0.14g, 1.0
mmol) and 3,4-methylenedioxybenzyl alcohol (0.30g, 2.0 mmol). After
purification by column chromatography, the compound was isolated as a
white solid (0.26g, 0.9 mmol, 97%). Mp = 94–95 C. 1H NMR (400 MHz,
CDCl3): δ = 7.72 (d, J = 8.1 Hz, 1H), 7.26 (t, J = 7.7 Hz, 1H), 6.75–6.61 (m,
5H), 5.92 (s, 2H), 3.23 (t, J = 7.9 Hz, 2H), 2.96 (t, J = 7.8 Hz, 2H) ppm. 13
C
NMR (100 MHz, CDCl3): δ = 201.6, 150.5, 147.8, 145.9, 135.4, 134.4,
131.1, 121.3, 118.0, 117.5, 116.0, 109.1, 108.4, 100.9, 41.3, 30.5 ppm.
HRMS (ESI): calcd. for C16H15NO3 ([M+H]): 270.1125, found: 270.1111.
1-(2-aminophenyl)-3-(furan-2-yl)propan-1-one (Table 2, compound 2i)[21b]
:
Prepared from 2’-aminoacetophenone (0.14g, 1.0 mmol) and 2-
furylmethanol (0.20g, 2.0 mmol). After purification by column
chromatography, the compound was isolated as a pale yellow solid (0.17g,
0.7 mmol, 78%). Mp = 77–78 C. 1H NMR (400 MHz, CDCl3): δ = 7.78 (d,
J = 8.6 Hz, 1H), 7.35 (d, J = 1.8 Hz, 1H), 7.29 (t, J = 7.7 Hz, 1H), 6.68 (t, J
= 7.5 Hz, 2H), 6.32–6.31 (m, 1H), 6.07 (d, J = 3.1 Hz, 1H), 3.34 (t, J = 7.6
Hz, 2H), 3.09 (t, J = 7.6 Hz, 2H) ppm. 13C NMR (100 MHz, CDCl3): δ =
200.9, 155.2, 150.4, 141.2, 134.5, 131.1, 118.0, 117.5, 116.0, 110.4, 105.3,
37.5, 23.0 ppm. HRMS (ESI): calcd. for C13H13NO2 ([M+H]): 216.1019,
found: 216.1015.
1-(2-aminophenyl)-3-(p-tolyl)propan-1-one (Table 2, compound 2d)[new]
:
Prepared from 2’-aminoacetophenone (0.14g, 1.0 mmol) and 4-
methylbenzyl alcohol (0.24g, 2.0 mmol). After purification by column
chromatography, the compound was isolated as a yellow liquid (0.22g, 0.9
mmol, 92%). 1H NMR (400 MHz, CDCl3): δ = 7.75 (d, J = 8.1 Hz, 1H), 7.29
(d, J = 7.2 Hz, 1H), 7.16–7.09 (m, 4H), 6.77–6.66 (m, 2H), 3.26 (t, J = 7.6
Hz, 2H), 3.01 (t, J = 7.7 Hz, 2H), 2.33 (s, 3H) ppm. 13C NMR (100 MHz,
CDCl3): δ = 201.9, 138.5, 135.7, 134.4, 131.2, 129.3, 128.4, 118.3, 118.1,
117.0, 116.7, 41.3, 30.3, 21.1 ppm. HRMS (ESI): calcd. for C16H17NO
([M+H]): 240.1383, found: 240.1403. IR (KBr): ʋ (cm-1) = 3474, 3345, 3132,
3094, 1651, 1584, 1514, 1450, 971, 811, 749.
1-(4-aminophenyl)-3-(p-tolyl)propan-1-one (Table 2, compound 2j)[new]
:
Prepared from 4’-aminoacetophenone (0.14g, 1.0 mmol) and 4-
methylbenzyl alcohol (0.24g, 2.0 mmol). After purification by column
chromatography, the compound was isolated as a white solid (0.17g,
0.7mmol, 73%). Mp = 96–97 oC.1H NMR (400 MHz, CDCl3): δ = 7.82 (d, J
= 8.7 Hz, 2H), 7.16–7.10 (m, 4H), 6.64 (d, J = 8.7 Hz, 2H), 3.19 (t, J = 7.5
Hz, 2H), 3.01 (t, J = 7.7 Hz, 2H), 2.33 (s, 3H) ppm. 13C NMR (100 MHz,
CDCl3): δ = 197.8, 151.2, 138.7, 135.6, 130.6, 129.3, 128.4, 127.6, 113.9,
40.1, 30.2, 21.1ppm.HRMS (ESI): calcd. for C16H17NO ([M+H]): 240.1383,
found: 240.1401. IR (KBr): ʋ (cm-1) = 3461, 3360, 3226, 3034, 2919, 1647,
1631, 1590, 1175, 832, 809.
1-(2-aminophenyl)-3-(o-tolyl)propan-1-one (Table 2, compound 2e)[new]
:
Prepared from 2’-aminoacetophenone (0.14g, 1.0 mmol) and 2-
methylbenzyl alcohol (0.24g, 2.0 mmol). After purification by column
chromatography, the compound was isolated as a white solid (0.21g, 0.8
mmol, 88%). Mp = 57–58 C. 1H NMR (400 MHz, CDCl3): δ = 7.75 (d, J =
8.1 Hz, 1H), 7.31–7.26 (m, 1H), 7.20–7.14 (m, 4H), 6.73 (d, J = 8.2 Hz,
1H), 6.68 (t, J = 7.6 Hz, 1H)., 3.23 (t, J = 7.6 Hz, 2H), 3.04 (t, J = 7.6 Hz,
2H), 2.36 (s, 3H) ppm. 13C NMR (100 MHz, CDCl3): δ = 201.9, 149.6, 139.7,
136.2, 134.5, 131.1, 130.5, 128.8, 126.4, 126.3, 118.4, 118.0, 116.6, 39.8,
28.1, 19.5 ppm. HRMS (ESI): calcd. for C16H17NO ([M+H]): 240.1383,
found: 240.1377. IR (KBr): ʋ (cm-1) = 3452, 3339, 2912, 1641, 1581, 1551,
1198, 1160, 750.
1-(4-aminophenyl)-3-(4-fluorophenyl)propan-1-one (Table 2, compound
2k)[new]: Prepared from 4’-aminoacetophenone (0.14g, 1.0 mmol) and 4-
fluorobenzyl alcohol (0.25g, 2.0 mmol). After purification by column
chromatography, the compound was isolated as a white solid (0.21g, 0.8
mmol, 86%). Mp = 94–95 oC.1H NMR (400 MHz, CDCl3): δ = 7.80 (d, J =
8.6 Hz, 2H), 7.21–7.17 (m, 2H), 6.96 (t, J = 8.7 Hz, 2H), 6.64 (d, J = 8.3
Hz, 2H), 3.17 (t, J = 7.6 Hz, 2H), 3.01 (t, J = 7.6 Hz, 2H) ppm. 13C NMR
(100 MHz, CDCl3): δ = 197.5, 161.5 (d, J = 243.5 Hz), 151.2, 137.4 (d, J =
3.1 Hz), 130.7, 129.9 (d, J = 7.8 Hz), 128.6 (d, J = 5.5 Hz), 115.3 (d, J =
21.1 Hz), 114.0, 39.9, 29.8 ppm. 19F NMR (376 MHz, CDCl3): δ = -118.5
ppm. HRMS (ESI): calcd. for C15H14FNO ([M+H]): 244.1132, found:
244.1121. IR (KBr): ʋ (cm-1) = 3446, 3344, 3234, 1640, 1593, 1510, 1215,
1175, 978, 826.
1-(2-aminophenyl)-3-(4-(trifluoromethyl)phenyl)propan-1-one(Table
2,
compound 2f)[new]: Prepared from 2’-aminoacetophenone (0.14g, 1.0
mmol) and 4-trifluromethylbenzyl alcohol (0.35g , 2.0 mmol). After
purification by column chromatography, the compound was isolated as a
white solid (0.18g, 0.6 mmol 65% ).Mp = 95–96 oC.1H NMR (400 MHz,
C6D6): δ = 7.30 (d, J = 7.7 Hz, 3H), 7.00 (t, J = 7.5 Hz, 1H), 6.80 (d, J = 7.6
Hz, 2H), 6.44 (t, J = 7.5 Hz, 1H), 6.13 (d, J = 8.1 Hz, 1H), 5.95 (s, 2H), 2.78
(t, J = 7.1 Hz, 2H), 2.68 (t, J = 6.9 Hz, 2H) ppm.13C NMR (100 MHz, CDCl3):
δ = 200.3, 150.9, 146.3, 134.3, 131.2, 129.11, 125.5 (q, J = 3.8 Hz), 118.0,
117.4, 115.5, 40.3, 30.2 ppm.HRMS (ESI): calcd. for C16H14F3NO ([M+H]):
294.1100, found: 294.1123. IR (KBr): ʋ (cm-1) = 3489, 3352, 1652, 1614,
1589, 1328, 1163, 1100, 1067, 830, 746.
1-(4-amino-[1,1'-biphenyl]-3-yl)-3-phenylpropan-1-one
(Table
2,
compound 2l)[new]: Prepared from 1-(4-amino-[1,1'-biphenyl]-3-yl)ethanone
(0.21g, 1.0 mmol) and benzyl alcohol (0.22g, 2.0 mmol). After purification
by column chromatography, the compound was isolated as a white solid
(0.27g, 0.9 mmol, 91%). Mp = 122–123 oC.1H NMR (400 MHz, CDCl3): δ
= 7.96 (d, J = 2.1 Hz, 1H), 7.56–7.51 (m, 3H), 7.43 (t, J = 7.7 Hz, 2H),
7.36–7.22 (m, 6H), 6.77 (d, J = 8.6 Hz, 1H), 3.37 (t, J = 7.7 Hz, 2H), 3.10
(t, J = 7.6 Hz, 2H) ppm. 13C NMR (100 MHz, CDCl3): δ = 201.7, 149.6,
141.6, 140.6, 133.3, 129.5, 129.3, 128.9, 128.7, 128.6, 126.7, 126.4, 126.2,
1-(3-(benzylamino)phenyl)-3-phenylpropan-1-one (Table 2, compound
2g)[new]: Prepared from 3’-aminoacetophenone (0.14g, 1.0 mmol) and
benzyl alcohol (0.22g, 2.0 mmol). After purification by column
chromatography, the compound was isolated as a white solid (0.19g, 0.6
mmol, 61%). Mp = 83–84 C. 1H NMR (400 MHz, CDCl3): δ = 7.37–7.20
(m, 13H), 6.82 (dd, J = 8.4, 2.9 Hz, 1H), 4.37 (s, 2H), 3.25 (t, J = 7.7 Hz,
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