Molecules 2018, 23, 764
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1-(Pent-4-en-2-yl)isoquinoline (
8
). This compound was prepared according to General Procedure B using
N-(pent-4-enyl-2-carbonyloxy)phthalimide (77.7 mg, 0.30 mmol) and isoquinoline (25.8 mg, 0.20 mmol).
Purifications of the crude product by flash column chromatography (SiO2, cHex/EtOAc 8/1) afforded
c
the title compound (33.1 mg, 1.68
×
10−4 mol, 84%) as a yellow oil. Rf = 0.47 (SiO2, Hex/EtOAc
8/1). IR (ATR): νe [cm−1] 3052, 2969, 2928, 1639, 1622, 1374, 994, 913, 822, 798. 1H-NMR, COSY
(300 MHz, CDCl3): δ/ppm 8.50 (d, J = 5.8 Hz, 1H, H-3), 8.23–8.20 (m, 1H, H-8), 7.83–7.80 (m, 1H, H-5),
7.62 (mc, 2H, H-6,7), 7.49 (dd, J = 5.8, 0.9 Hz, 1H, H-4), 5.83 (ddd, J = 17.1, 10.2, 7.7 Hz, 1H, H-40),
5.08–5.02 (m, 2H, H-50), 3.87 (sept, J = 6.8 Hz, 1H, H-20), 2.79–2.74 (m, 1H, H-30), 2.50 (mc, 1H, H-30),
1.43 (d, J = 6.8 Hz, 1H, H-10). 13C, HSQC, HMBC (75.4 MHz, CDCl3): δ/ppm 165.2 (Cq-1), 142.0 (C-3),
137.4 (C-40), 136.5 (Cq-4a), 129.7 (C-6), 127.7 (C-5), 127.0 (C-7), 126.7 (Cq-8a), 124.8 (C-8), 119.1 (C-4),
116.6 (C-50), 40.9 (C-30), 36.2 (C-20), 20.3 (C-10). ESI-MS (pos): m/z 198.1 (100%, [M + H]+). ESI-HRMS
(pos): m/z calculated for [C14H15N]+ m/z 198.1277, found 198.1278.
1-(Pentan-1-yl)isoquinoline (9). This compound was prepared according to General Procedure B using
N-(hexanoyloxy)phthalimide (78.4 mg, 0.30 mmol) and isoquinoline (25.8 mg, 0.20 mmol). Purifications
of the crude product by flash column chromatography (SiO2, cHex/EtOAc 15/1) afforded the title
−5
compound (6.6 mg, 3.31
×
10 mol, 17%) as a yellow oil. Rf = 0.35 (SiO2, cHex/EtOAc 5/1). IR (ATR):
νe [cm−1] 2926, 2852, 1562, 1449, 1391, 1335, 993, 822, 744, 675. H-NMR, COSY (300 MHz, CDCl3):
1
δ
/ppm 8.43 (d, J = 5.8 Hz, 1H, H-3), 8.16 (d, J = 8.5, 1.1 Hz, 1H, H-8), 7.83–7.80 (m, 1H, H-5),
0
0
7.63 (mc, 2H, H-6,7), 7.50 (dd, J = 5.8, 0.9 Hz, 1H, H-4), 3.32–3.26 (m, 2H, H-1 ), 1.92–1.84 (m, 2H, H-2 ),
1.50–1.40 (m, 2H, H-3‘,4 ), 0.92 (t, J = 7.1 Hz, 3H, H-5 ). 13C, HSQC, HMBC (75.4 MHz, CDCl3):
δ/ppm
0
0
162.2 (Cq-1), 142.2 (C-3), 136.4 (Cq-4a), 129.9 (C-6), 127.5 (C-5), 127.1 (C-7), 125.5 (C-8), 124.1 (Cq-8a),
119.3 (C-4), 35.7 (C-10), 32.3 (C-30), 29.7 (C-20), 22.8 (C-40), 14.2 (C-50). ESI-MS (pos): m/z 200.1
(100%, [M + H]+). The spectral data are consistent with those reported in the literature [37].
tert-Butyl-[1-(isoquinolin-2-yl)-2-methylpropyl]carbamate (11). This compound was prepared according to
General Procedure B using N-(N-tert-butoxycarbonyl-L-valinyloxy)phthalimide (108.7 mg, 0.30 mmol)
and isoquinoline (25.8 mg, 0.20 mmol). Purifications of the crude product by flash column
c
chromatography (SiO2, Hex/EtOAc 8/1) afforded the title compound (41.9 mg, 1.39
×
10−4 mol,
70%) as a colorless solid. Rf = 0.31 (SiO2, cHex/EtOAc 8/1). Mp: 108.3–109.9 ◦C. IR (ATR): νe [cm−1
]
1
3631, 2969, 2931, 1718, 1508, 1459, 1170, 903, 727, 649. H-NMR, COSY (300 MHz, CDCl3):
δ/ppm
8.46 (d, J = 5.7 Hz, 1H, H-3), 8.24 (d, J = 8.3 Hz, 1H, H-8), 7.84–7.81 (m, 1H, H-5), 7.65 (mc, 2H,
H-6,7), 7.55 (dd, J = 5.7, 0.9 Hz, 1H, H-4), 6.07 (d, J = 9.1 Hz, 1H, NH), 5.54 (dd, J = 9.1, 5.7 Hz, 1H,
H-20), 2.25–2.16 (m, 1H, H-30), 1.44 (s, 9H, C(CH3)3), 0.96 (d, J = 6.8 Hz, 1H, CH3), 0.87 (d, J = 6.8 Hz,
1H, CH3). 13C, HSQC, HMBC (75.4 MHz, CDCl3):
δ/ppm 160.4 (Cq-1), 156.2 (CO), 141.4 (C-3),
136.4 (Cq-4a), 130.1 (C-6), 127.5 (2C, C-5,7), 126.2 (Cq-8a), 125.0 (C-8), 120.1 (C-4), 79.2 (Cq(CH3)3),
55.6 (C-20), 34.9 (CH(CH3)2), 28.6 (3C, (CH3)3), 20.5 (CH3), 17.6 (CH3) . ESI-MS (pos): m/z 301.2
(100%, [M + H]+). ESI-HRMS (pos): m/z calculated for [C18H24N2O2]+ m/z 301.1911, found 301.1909.
2-Cyclohexyl-1,3-benzothiazole (14). This compound was prepared according to General Procedure B
using N-(cyclohexycarbonyloxy)phthalimide (82.0 mg, 0.30 mmol) and 1,3-benzothiazole (27.0 mg,
0.20 mmol). Purifications of the crude product by flash column chromatography (SiO2, cHex/EtOAc
8/1) afforded the title compound (37.8 mg, 1.74
×
10−4 mol, 87%) as a colorless oil. Rf = 0.48
(SiO2, cHex/EtOAc 8/1). IR (ATR): νe [cm−1] 2926, 2851, 1514, 1448, 1437, 1244, 1014, 757, 728, 668.
1H-NMR, COSY (300 MHz, CDCl3):
δ/ppm 7.97 (dt, J = 8.2, 1.0 Hz, 1H, H-4), 7.86–7.83 (m, 1H, H-7),
7.44 (ddd, J = 8.3, 7.2, 1.3 Hz, 1H, H-5), 7.33 (ddd, J = 8.3, 7.2, 1.3 Hz, 1H, H-6), 3.10 (tt, J = 11.6,
3.6 Hz, 1H,0H-10), 2.23–2.18 (m, 2H, H-20), 1.88–1.85 (m, 2H, H-30), 1.76–1.67 (m, 3H, H-40,60), 1.52–1.38
0
(m, 3H, H-4 ,5 ). 13C, HSQC, HMBC (75.4 MHz, CDCl3):0δ/ppm 177.7 (Cq-2), 153.2 (Cq-3a), 134.2 (Cq-7a),
0
0
0
0
0
125.9 (C-5), 124.6 (C-6), 122.7 (C-4), 121.7 (C-7), 43.6 (C-1 ), 33.6 (2C, C-2 ,6 ), 26.2 (2C, C-3 ,5 ), 25.7 (C-4 ).
ESI-MS (pos): m/z 218.0 (100%, [M + H]+). The spectral data are consistent with those reported