F
N. Guranova et al.
Paper
Synthesis
Methyl 2-Isobutyl-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-car-
boxylate (10f)
Methyl 2-(Furan-2-ylmethyl)-1-oxo-1,2,3,4-tetrahydroisoquino-
line-4-carboxylate (10j)
Eluted with EtOAc–n-hexane (1:5).
Eluted with EtOAc–n-hexane (1:5).
Yield: 64 mg (41%); transparent viscous oil.
Yield: 52 mg (32%); yellow oil.
1H NMR (400 MHz, СDCl3): δ = 8.13 (dd, J = 7.7, 1.6 Hz, 1 H), 7.49
(td, J = 7.4, 1.7 Hz, 1 H), 7.43 (td, J = 7.4, 1.6 Hz, 1 H), 7.31–7.27 (m,
1 H), 3.93 (dd, J = 12.3, 3.7 Hz, 1 H), 3.89–3.85 (m, 1 H), 3.80 (dd,
J = 12.3, 3.7 Hz, 1 H), 3.70 (s, 3 H), 3.45 (dd, J = 13.4, 7.0 Hz, 1 H), 3.37
(dd, J = 13.4, 7.0 Hz, 1 H), 1.98–2.12 (m, 1 H), 0.96 (d, J = 6.7 Hz, 3 H),
0.95 (d, J = 6.6 Hz, 3 H).
1H NMR (400 MHz, CDCl3): δ = 8.16 (dd, J = 7.6, 1.6 Hz, 1 H), 7.50 (td,
J = 7.4, 1.6 Hz, 1 H), 7.44 (td, J = 7.4, 1.6 Hz, 1 H), 7.38 (t, J = 1.4 Hz,
1 H), 7.32–7.26 (m, 1 H), 6.37–6.32 (m, 2 H), 4.94 (d, J = 15.3 Hz, 1 H),
4.66 (d, J = 15.3 Hz, 1 H), 3.99 (dd, J = 12.4, 3.7 Hz, 1 H), 3.86 (t,
J = 4.2 Hz, 1 H), 3.79 (dd, J = 12.5, 4.6 Hz, 1 H), 3.65 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 171.1, 163.5, 150.5, 142.4, 134.8,
131.9, 129.0, 128.7, 128.3, 127.8, 110.4, 108.7, 52.6, 47.4, 43.7, 43.3.
13C NMR (101 MHz, CDCl3): δ = 171.4, 163.8, 134.6, 131.7, 129.3,
128.6, 128.2, 127.7, 54.7, 52.6, 48.3, 43.8, 27.1, 20.2, 20.1.
HRMS (ESI): m/z [M + H]+ calcd for C15H20NO3: 262.1449; found:
HRMS (ESI): m/z [M + H]+ calcd for C16H16NO4: 286.1074; found:
286.1078.
262.1438.
Methyl 2-(2-Chlorobenzyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-
4-carboxylate (10k)
Methyl 2-Cyclopropyl-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-
carboxylate (10g)
Eluted with EtOAc–n-hexane (1:10).
Eluted with EtOAc–n-hexane (1:5).
Yield: 52 mg (28%); amorphous white solid; mp 100–102 °C.
Yield: 37 mg (24%); transparent viscous oil.
1H NMR (400 MHz, CDCl3): δ = 8.19 (dd, J = 7.6, 1.6 Hz, 1 H), 7.51 (td,
J = 7.4, 1.5 Hz, 1 H), 7.46 (td, J = 7.4, 1.5 Hz, 1 H), 7.41–7.38 (m, 2 H),
7.32–7.19 (m, 3 H), 4.99 (d, J = 15.3 Hz, 1 H), 4.93 (d, J = 15.3 Hz, 1 H),
3.92 (dd, J = 12.3, 3.6 Hz, 1 H), 3.90–3.82 (m, 1 H), 3.80 (dd, J = 12.3,
4.5 Hz, 1 H), 3.60 (s, 3 H).
1H NMR (400 MHz, СDCl3): δ = 8.09 (dd, J = 7.7, 1.5 Hz, 1 H), 7.44 (td,
J = 7.5, 1.6 Hz, 1 H), 7.38 (td, J = 7.5, 1.6 Hz, 1 H), 7.30–7.22 (m, 1 H),
3.98–3.87 (m, 1 H), 3.75–3.80 (m, 2 H), 3.63 (s, 3 H), 2.85–2.75 (m,
1 H), 1.03–0.91 (m, 1 H), 0.85–0.69 (m, 3 H).
13C NMR (101 MHz, CDCl3): δ = 171.1, 165.5, 134.7, 131.8, 129.4,
128.3, 128.2, 128.1, 52.5, 48.6, 43.9, 30.0, 8.3, 6.1.
HRMS (ESI): m/z [M + H]+ calcd for C14H16NO3: 246.1125; found:
246.1134.
13C NMR (101 MHz, CDCl3): δ = 171.1, 163.9, 134.9, 134.4, 133.7,
132.0, 130.2, 129.6, 128.9, 128.8, 128.7, 128.3, 127.8, 127.1, 52.5, 48.0,
47.7, 43.7.
HRMS (ESI): m/z [M + H]+ calcd for C18H17ClNO3: 330.0891; found:
330.0893.
Methyl 2-(3-Ethoxypropyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-
4-carboxylate (10h)
Methyl 2-Cyclopentyl-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-
carboxylate (10l)
Eluted with EtOAc–n-hexane (1:1).
Eluted with EtOAc–n-hexane (1:5).
Yield: 81 mg (44%); transparent oil.
Yield: 109 mg (66%); transparent oil.
1H NMR (400 MHz, CDCl3): δ = 8.09 (dd, J = 7.6, 1.5 Hz, 1 H), 7.46 (td,
J = 7.4, 1.6 Hz, 1 H), 7.40 (td, J = 7.6, 1.4 Hz, 1 H), 7.28 (dd, J = 7.3,
1.4 Hz, 1 H), 3.93 (dd, J = 11.8, 3.2 Hz, 1 H), 3.86–3.82 (m, 2 H), 3.75–
3.66 (m, 1 H), 3.68 (s, 3 H), 3.60 (dt, J = 13.7, 7.0 Hz, 1 H), 3.51–3.43
(m, 2 H), 3.47 (q, J = 7.1 Hz, 2 H), 1.86–1.97 (m, 2 H), 1.17 (t, J = 7.0 Hz,
3 H).
1H NMR (400 MHz, CDCl3): δ = 8.10 (dd, J = 7.6, 1.6 Hz, 1 H), 7.44 (td,
J = 7.4, 1.6 Hz, 1 H), 7.39 (td, J = 7.4, 1.6 Hz, 1 H), 7.24 (dd, J = 7.6,
1.6 Hz, 1 H), 5.15 (p, J = 8.5 Hz, 1 H), 3.88–3.81 (m, 2 H), 3.66 (s, 3 H),
3.64–3.58 (m, 1 H), 1.96–1.42 (m, 8 H).
13C NMR (101 MHz, CDCl3): δ = 171.2, 163.6, 134.5, 131.6, 129.7,
128.6, 128.1, 127.6, 53.9, 52.5, 43.7, 42.4, 28.4, 28.1, 24.4, 24.2.
13C NMR (101 MHz, CDCl3): δ = 171.2, 163.6, 134.7, 131.7, 129.2,
128.3, 128.2, 127.8, 68.1, 66.2, 52.6, 48.0, 45.1, 43.7, 27.9, 15.2.
HRMS (ESI): m/z [M + H]+ calcd for C16H22NO4: 292.1543; found:
HRMS (ESI): m/z [M + H]+ calcd for C16H20NO3: 274.1438; found:
274.1442.
292.1537.
Methyl 2-(3,4-Dimethoxyphenethyl)-1-oxo-1,2,3,4-tetrahydroiso-
quinoline-4-carboxylate (10m)
Methyl 2-[2-(tert-Butylthio)ethyl]-1-oxo-1,2,3,4-tetrahydroiso-
quinoline-4-carboxylate (10i)
Eluted with EtOAc.
Eluted with EtOAc–n-hexane (1:7).
Yield: 59 mg (26%); yellow oil.
Yield: 44 mg (22%); white amorphous solid; mp 108–110 °C.
1H NMR (400 MHz, CDCl3): δ = 8.14 (dd, J = 7.6, 1.6 Hz, 1 H), 7.50 (td,
J = 7.4, 1.7 Hz, 1 H), 7.45 (td, J = 7.5, 1.4 Hz, 1 H), 7.31 (d, J = 1.4 Hz,
1 H), 6.83 (s, 3 H), 3.96–3.84 (m, 2 H), 3.88 (s, 6 H), 3.84–3.81 (m, 1 H),
3.77–3.67 (m, 2 H), 3.69 (s, 3 H), 3.02–2.85 (m, 2 H).
13C NMR (101 MHz, CDCl3): δ = 171.2, 163.5, 149.0, 147.6, 134.7,
131.8, 131.5, 129.2, 128.3, 128.3, 127.9, 120.7, 112.1, 111.4, 55.9, 55.8,
52.6, 49.9, 48.5, 43.7, 33.5.
1H NMR (400 MHz, CDCl3): δ = 8.10 (dd, J = 7.7, 1.5 Hz, 1 H), 7.48 (td,
J = 7.5, 1.6 Hz, 1 H), 7.42 (td, J = 7.5, 1.6 Hz, 1 H), 7.34–7.24 (m, 1 H),
3.97 (dd, J = 12.2, 3.6 Hz, 1 H), 3.93–3.84 (m, 2 H), 3.80–3.71 (m, 2 H),
3.70 (s, 3 H), 2.82 (t, J = 7.6 Hz, 2 H), 1.36 (s, 9 H).
13C NMR (101 MHz, CDCl3): δ = 171.1, 163.5, 134.8, 131.8, 129.1,
128.3, 128.3, 127.9, 52.6, 49.1, 48.8, 43.7, 42.6, 31.1 (3C), 26.2.
HRMS (ESI): m/z [M + H]+ calcd for C17H24NO3S: 344.1291; found:
HRMS (ESI): m/z [M + H]+ calcd for C21H24NO5: 370.1649; found:
344.1281.
370.1661.
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2018, 50, A–H