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R. Gómez Arrayás et al.
FEATURE ARTICLE
1H NMR (300 MHz): d = 8.58–8.56 (m, 1 H), 7.96–7.93 (m, 1 H),
7.85 (td, J = 7.7, 1.6 Hz, 1 H), 7.43 (ddd, J = 7.7, 4.8, 1.2 Hz, 1 H),
7.19–7.04 (m, 7 H), 6.95 (td, J = 7.5, 1.4 Hz, 1 H), 6.78–6.73 (m, 2
H), 6.04 (ddd, J = 9.5, 5.5, 0.8 Hz, 1 H), 5.41 (d, J = 7.9 Hz, 1 H),
4.69 (dd, J = 8.3, 2.6 Hz, 1 H), 4.01 (dd, J = 5.7, 2.8 Hz, 1 H).
13C NMR (75 MHz): d = 158.2, 149.9, 138.6, 137.8, 132.6, 131.2,
128.8, 128.7, 128.5, 128.3, 128.0, 127.9, 127.1, 126.5, 126.3, 121.7,
58.4, 47.7.
(1S*,2S*)-2-[3¢,5¢-Bis(trifluoromethyl)phenyl]-N-[(2¢-pyrid-
yl)sulfonyl]-1,2-dihydronaphthalen-1-amine (anti-22k)
Chromatography: n-hexane–EtOAc (2:1); yield: 96.7 mg (97%);
white solid; mp 218–219 °C.
1H NMR (300 MHz): d = 8.61 (d, J = 4.9 Hz, 1 H), 7.98 (d, J = 7.7
Hz, 1 H), 7.90 (td, J = 7.5, 1.6 Hz, 1 H), 7.67 (s, 1 H), 7.57 (s, 2 H),
7.49 (ddd, J = 7.5, 4.6, 1.2 Hz, 1 H), 7.29 (td, J = 7.1, 1.0 Hz, 1 H),
7.21 (d, J = 6.5 Hz, 1 H), 7.09 (dt, J = 7.5, 1.4 Hz, 1 H), 6.93 (d,
J = 7.1 Hz, 1 H), 6.88 (d, J = 9.5 Hz, 1 H), 6.04 (dd, J = 9.7, 5.3 Hz,
1 H), 5.51 (d, J = 7.9 Hz, 1 H), 4.75 (dd, J = 7.9, 3.4 Hz, 1 H), 4.22
(t, J = 4.4 Hz, 1 H).
MS (EI): m/z (%) = 220 (50, [M+ – (SO2Py)]), 204 (100), 115 (12),
91 (13), 78 (13).
(1S*,2S*)-2-(4-Methoxyphenyl)-N-[(2¢-pyridyl)sulfonyl]-1,2-di-
hydronaphthalen-1-amine (anti-22h)
Chromatography: n-hexane–EtOAc (2:1); yield: 76.9 mg (98%);
13C NMR (75 MHz): d = 158.1, 150.0, 141.8, 138.0, 132.1, 131.8
(q, JC,F = 33.0 Hz), 130.4, 129.7, 129.4, 128.8, 128.7, 128.4 (m),
126.9, 126.6, 126.4, 124.9, 121.7, 121.3 (m), 58.2, 47.1.
white solid; mp 160–161 °C.
MS (EI): m/z (%) = 356 (46, [M+ – (SO2Py)]), 340 (100), 79 (17).
1H NMR (300 MHz): d = 8.56 (dq, J = 4.6, 1.0 Hz, 1 H), 7.93 (dt,
J = 7.9, 1.0 Hz, 1 H), 7.84 (td, J = 7.7, 1.6 Hz, 1 H), 7.43 (ddd,
J = 7.5, 4.6, 1.2 Hz, 1 H), 7.18 (td, J = 7.5, 1.2 Hz, 1 H), 7.10 (dd,
J = 7.5, 1.4 Hz, 1 H), 6.98–6.92 (m, 3 H), 6.77 (dd, J = 7.5, 0.6 Hz,
1 H), 6.72 (d, J = 9.5 Hz, 1 H), 6.68–6.64 (m, 2 H), 6.03 (ddd,
J = 9.5, 5.4, 1.0 Hz, 1 H), 5.36 (d, J = 8.5 Hz, 1 H), 4.64 (dd, J = 8.1,
2.8 Hz, 1 H), 3.96–3.93 (m, 1 H), 3.70 (s, 3 H).
13C NMR (75 MHz): d = 158.6, 158.2, 149.9, 137.7, 132.6, 131.3,
130.5, 129.0, 128.8, 128.7, 127.9, 127.8, 126.5, 126.3, 121.7, 114.0,
113.9, 58.6, 55.1, 46.9.
(1S*,2S*)-2-(1¢-Naphthyl)-N-[(2¢-pyridyl)sulfonyl]-1,2-di-
hydronaphthalen-1-amine (anti-22l)
Chromatography: n-hexane–EtOAc (2:1); yield: 75.1 mg (91%);
white solid; mp 132–133 °C.
1H NMR (300 MHz): d = 8.46–8.41 (m, 2 H), 7.87 (dt, J = 7.7, 1.0
Hz, 1 H), 7.82 (dd, J = 7.8, 1.2 Hz, 1 H), 7.75 (td, J = 7.7, 1.6 Hz, 1
H), 7.64–7.58 (m, 2 H), 7.53–7.48 (m, 1 H), 7.35 (ddd, J = 7.7, 4.6,
1.2 Hz, 1 H), 7.20–7.11 (m, 3 H), 7.05 (dd, J = 7.3, 1.4 Hz, 1 H),
6.89–6.83 (m, 2 H), 6.57 (d, J = 7.3 Hz, 1 H), 6.13 (dd, J = 9.5, 6.5
Hz, 1 H), 5.58 (d, J = 8.1 Hz, 1 H), 4.86–4.81 (m, 2 H).
13C NMR (75 MHz): d = 157.9, 149.8, 137.5, 134.2, 132.8, 132.3,
131.9, 131.5, 129.0, 128.9, 128.7, 128.6, 128.5, 127.9, 127.8, 126.7,
126.5, 126.2, 125.6, 125.3, 125.1, 123.6, 121.7, 57.1, 43.3.
MS (EI): m/z (%) = 250 (33, [M+ – (SO2Py)]), 234 (100), 219 (13),
78 (11).
(1S*,2S*)-2-(4-Fluorophenyl)-N-[(2¢-pyridyl)sulfonyl]-1,2-di-
hydronaphthalen-1-amine (anti-22i)
Chromatography: n-hexane–EtOAc (2:1); yield: 70.0 mg (92%);
MS (EI): m/z (%) = 270 (27, [M+ – (SO2Py)]), 254 (100), 253 (56),
126 (13), 78 (15).
white solid; mp 183–184 °C.
1H NMR (300 MHz): d = 8.54–8.52 (m, 1 H), 7.89 (dt, J = 7.9, 1.0
Hz, 1 H), 7.82 (td, J = 7.7, 1.8 Hz, 1 H), 7.41 (ddd, J = 7.5, 4.6, 1.2
Hz, 1 H), 7.17 (td, J = 7.5, 1.4 Hz, 1 H), 7.08 (dd, J = 7.3, 1.2 Hz, 1
H), 7.02–6.97 (m, 2 H), 6.93 (dd, J = 7.5, 1.4 Hz, 1 H), 6.80–6.73
(m, 3 H), 6.70 (d, J = 9.7 Hz, 1 H), 5.99 (ddd, J = 9.5, 4.8, 1.2 Hz,
1 H), 5.34 (d, J = 8.3 Hz, 1 H), 4.62 (dd, J = 8.3, 3.2 Hz, 1 H), 3.99–
3.96 (m, 1 H).
13C NMR (75 MHz): d = 161.9 (d, JC,F = 244.0 Hz), 158.2, 149.9,
137.7, 134.3 (d, JC,F = 3.0 Hz), 132.5, 131.1, 129.6 (d, JC,F = 8.4
Hz), 128.9, 128.7, 128.3, 128.2, 128.1, 126.6, 126.4, 121.7, 115.3
(d, JC-F = 20.9 Hz), 58.6, 46.9.
(1S*,2S*)-2-(2¢,4¢,6¢-Trimethylphenyl)-N-[(2¢-pyridyl)sulfonyl]-
1,2-dihydronaphthalen-1-amine (anti-22m)
Chromatography: n-hexane–EtOAc (2:1); yield: 49.3 mg (87% in
converted product, 30% of starting material was recovered); white
solid; mp 152–153 °C.
1H NMR (300 MHz): d = 8.44 (d, J = 4.2 Hz, 1 H), 7.67 (d, J = 6.1
Hz, 1 H), 7.57 (td, J = 7.9, 1.6 Hz, 1 H), 7.38 (d, J = 7.7 Hz, 1 H),
7.32-7.25 (m, 3 H), 7.11–7.08 (m, 1 H), 6.48–6.44 (m, 3 H), 5.76
(dd, J = 9.7, 2.4 Hz, 1 H), 5.47 (dd, J = 13.7, 9.5 Hz, 1 H), 5.00 (d,
J = 9.7 Hz, 1 H), 4.23 (dt, J = 13.9, 2.6 Hz, 1 H), 2.22 (s, 6 H), 2.13
(s, 3 H).
MS (EI): m/z = 238 (52, [M+ – (SO2Py)]), 222 (100), 109 (13), 78
(15).
13C NMR (75 MHz): d = 157.7, 149.6, 137.3, 137.2, 137.0, 135.7,
134.1, 133.6, 131.9, 130.0, 128.2, 128.1, 126.8, 126.5, 125.9, 125.4,
120.1, 57.4, 43.2, 21.8, 20.7.
(1S*,2S*)-2-(4-Methylphenyl)-N-[(2¢-pyridyl)sulfonyl]-1,2-di-
hydronaphthalen-1-amine (anti-22j)
Chromatography: n-hexane–EtOAc (2:1); yield: 68.5 mg (91%);
white solid; mp 183–184 °C.
MS (EI): m/z (%) = 262 (61, [M+ – (SO2Py)]), 246 (100), 231 (33),
78 (21).
(1S*,2R*)-N-[(2¢-Pyridyl)sulfonyl]-2-(2¢-thienyl)-1,2-dihydro-
naphthalen-1-amine (anti-22n)
Chromatography: n-hexane–EtOAc (2:1); yield: 48.6 mg (88% in
converted product, 25% of starting material was recovered); white
solid; mp 153–154 °C.
1H NMR (300 MHz): d = 8.59–8.56 (m, 1 H), 7.98 (d, J = 6.9 Hz, 1
H), 7.89 (td, J = 7.7, 1.8 Hz, 1 H), 7.44 (ddd, J = 7.7, 4.8, 1.2 Hz, 1
H), 7.20 (td, J = 7.5, 1.2 Hz, 1 H), 7.10 (d, J = 6.3 Hz, 1 H), 7.01–
6.95 (m, 2 H), 6.83–6.73 (m, 3 H), 6.67 (d, J = 9.7 Hz, 1 H), 6.11
(ddd, J = 9.5, 5.9, 1.0 Hz, 1 H), 5.46 (d, J = 8.3 Hz, 1 H), 4.75 (dd,
J = 8.1, 2.2 Hz, 1 H), 4.26 (dd, J = 5.6, 2.4 Hz, 1 H).
1H NMR (300 MHz): d = 8.57 (dq, J = 4.8, 1.0 Hz, 1 H), 7.94 (dt,
J = 7.9, 1.0 Hz, 1 H), 7.84 (td, J = 7.7, 1.6 Hz, 1 H), 7.43 (ddd,
J = 7.5, 4.6, 1.2 Hz, 1 H), 7.18 (td, J = 7.5, 1.4 Hz, 1 H), 7.10 (dd,
J = 7.5, 1.4 Hz, 1 H), 6.97–6.91 (m, 5 H), 6.77–6.71 (m, 2 H), 6.03
(ddd, J = 9.5, 5.5, 1.0 Hz, 1 H), 5.30 (d, J = 8.1 Hz, 1 H), 4.65 (dd,
J = 8.1, 3.0 Hz, 1 H), 3.96 (ddd, J = 5.5, 2.8, 1.0 Hz, 1 H), 2.22 (s,
3 H).
13C NMR (75 MHz): d = 158.2, 149.9, 137.7, 136.7, 135.4, 132.6,
131.3, 129.2, 128.8, 128.6, 127.9, 127.8, 126.5, 126.3, 121.8, 58.5,
47.3, 20.9.
MS (EI): m/z (%) = 234 (38, [M+ – (SO2Py)]), 218 (100), 202 (11),
78 (13).
13C NMR (75 MHz): d = 158.1, 149.9, 141.8, 137.8, 132.0, 131.1,
129.0, 128.9, 128.1, 128.0, 127.8, 126.7, 126.6, 126.4, 125.2, 124.2,
121.8, 58.3, 42.4.
Synthesis 2006, No. 7, 1205–1219 © Thieme Stuttgart · New York