Chatani et al.
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7.4, 4.9, 1.0 Hz, 1H), 7.23 (d, J = 1.0 Hz, 1H), 7.31 (dd, J =
7.9, 1.0 Hz, 1H), 7.55–7.60 (c, 2H), 7.74 (td, J = 7.9,
2.0 Hz, 1H), 8.60 (ddd, J = 4.9, 1.7, 1.0 Hz, 1H). 13C NMR
(CDCl3) δ: 8.61, 21.10, 36.48, 121.89, 121.94, 127.89,
128.61, 130.48, 135.29, 136.62, 138.76, 141.83, 149.09,
157.11, 208.26. MS m/z (relative intensity, %): 225 (M+, 1),
210 (3), 197 (14), 196 (100), 98 (10), 83 (17), 51 (12). Anal.
calcd. for C15H15NO: C 79.97, H 6.71, N 6.22; found: C
79.84, H 6.74, N 6.19.
NMR (CDCl3) δ: 0.95 (t, J = 7.3 Hz, 6H), 2.32 (q, J =
7.3 Hz, 4H), 2.45 (s, 3H), 7.25–7.34 (c, 2H), 7.34 (s, 2H),
7.70 (td, J = 7.6, 1.6 Hz, 1H), 8.62 (d, J = 4.6 Hz, 1H). 13C
NMR (CDCl3) δ: 8.32, 21.04, 36.17, 122.55, 124.78, 129.18,
133.55, 136.28, 138.69, 142.36, 149.56, 156.55, 207.35. MS
m/z (relative intensity, %): 281 (M+, 1), 253 (19), 252 (100),
195 (17), 167 (14), 166 (10), 84 (13). Anal. calcd. for
C18H19NO2: C 76.84, H 6.81, N 4.98; found: C 76.69, H
6.87, N 4.96.
1-[5-Methoxy-2-(2-pyridinyl)phenyl]-1-propanone (5e)
Light yellow solid, mp 125–130 °C (1 mmHg)
(1 mmHg = 133.322 4 Pa). Rf 0.11 (hexane–EtOAc, 1:2). IR
10-Benzo[h]quinolinyl-1-propanone (16)
White solid, mp 92 to 93 °C (1 mmHg) (1 mmHg =
133.322 4 Pa). Rf 0.54 (hexane–EtOAc, 1:1). IR (KBr):
1
1
(KBr): 1686, 1608, 1587, 1470, 1429, 1316, 1232. H NMR
1691 s. H NMR (CDCl3) δ: 1.41 (t, J = 7.3 Hz, 3H), 2.60
(CDCl3) δ: 1.09 (t, J = 7.3 Hz, 3H), 2.45 (q, J = 7.3 Hz, 2H),
3.86 (s, 3H), 6.92 (d, J = 2.6 Hz, 1H), 7.01 (dd, J = 8.6,
2.6 Hz, 1H), 7.17 (ddd, J = 7.6, 5.0, 1.0 Hz, 1H), 7.55 (d,
J = 7.9 Hz, 1H), 7.61 (d, J = 8.6 Hz, 1H), 7.72 (td, J = 7.7,
1.7 Hz, 1H), 8.57 (dd, J = 5.0, 1.0 Hz, 1H). 13C NMR
(CDCl3) δ: 8.57, 36.50, 55.47, 112.49, 115.36, 121.46,
121.60, 129.92, 130.40, 136.62, 143.29, 149.98, 156.64,
159.86, 207.82. MS m/z (relative intensity, %): 241 (M+, 1),
226 (1), 213 (15), 212 (100), 197 (22), 169 (27), 141 (14),
114 (10), 63 (11), 51 (13). Anal. calcd. for C15H15NO2: C
74.67, H 6.27, N 5.81; found: C 74.56, H 6.31, N 5.76.
(br, 1H), 3.08 (br, 1H), 7.47 (dd, J = 7.3, 0.99 Hz, 1H), 7.51
(dd, J = 7.9, 4.3 Hz, 1H), 7.72 (dd, J = 7.9, 7.3 Hz, 1H),
7.75 (d, J = 8.8 Hz, 1H), 7.87 (d, J = 8.8 Hz, 1H), 7.96 (dd,
J = 7.9, 0.99 Hz, 1H), 8.20 (dd, J = 7.9, 1.8 Hz, 1H), 8.90
(dd, J = 4.3, 1.8 Hz, 1H). 13C NMR (CDCl3) δ: 8.33, 37.82,
121.70, 124.48, 125.83, 126.93, 127.73, 127.83, 127.88,
128.65, 133.82, 135.57, 141.41, 144.95, 147.67, 209.43. MS
m/z (relative intensity, %): 235 (M+, 0), 207 (16), 206 (100),
178 (31), 89 (15), 75 (18). Anal. calcd. for C16H13NO: C
81.68, H 5.57, N 5.95; found: C 81.59, H 5.61, N 5.93.
1-(1-Naphthalenyl)isoquinoline (17)
1-[2-(2-Pyridinyl)-5-trifluoromethylphenyl]-1-propanone
(5f)
White solid, mp 116–119 °C (1 mmHg) (1 mmHg =
133.322 4 Pa). Rf 0.51 (hexane–EtOAc, 1:1). IR (KBr): 798,
1
Yellow oil, bp 160–165 °C (1 mmHg) (1 mmHg =
133.322 4 Pa). Rf 0.29 (hexane–EtOAc, 1:1). IR (neat):
775, 750. H NMR (CDCl3) δ: 7.28–7.50 (c, 4H), 7.55–7.70
(c, 4H), 7.74 (d, J = 5.6 Hz, 1H), 7.90–8.00 (c, 3H), 8.69 (d,
J = 5.6 Hz, 1H). 13C NMR (CDCl3) δ: 120.20, 125.15,
125.89, 125.93, 126.30, 126.83, 127.15, 127.61, 127.76,
128.22, 128.24, 128.80, 130.18, 132.26, 133.66, 136.42,
136.99, 142.37, 160.44. MS m/z (relative intensity, %): 255
(M+, 41), 254 (100), 253 (21), 127 (94), 113 (31). Anal.
calcd. for C19H13N: C 89.38, H 5.13, N 5.49; found: C
89.33, H 5.24, N 5.54.
1
1701, 1327, 1202, 1169, 1125, 1080. H NMR (CDCl3) δ:
1.11 (t, J = 7.3 Hz, 3H), 2.52 (q, J = 7.3 Hz, 2H), 7.30 (dd,
J = 7.6, 4.6 Hz, 1H), 7.64–7.68 (c, 2H), 7.73–7.85 (c, 3H),
8.64 (d, J = 5.0 Hz, 1H). 13C NMR (CDCl3) δ: 8.09, 36.14,
122.20, 122.82, 123.50, 123.98, 126.17, 128.90, 130.30,
136.89, 141.06, 142.25, 149.00, 155.17, 206.14. MS m/z
(relative intensity, %): 279 (M+, 0), 264 (2), 251 (14), 250
(100), 153 (10). Anal. calcd. for C15H12F3NO: C 64.52, H
4.33, N 5.02; found: C 64.40, H 4.47, N 5.06.
1-[2-(1-Isoquinolinyl)naphthalenyl]-1-propanone (18)
White solid, mp 135 to 136 °C (1 mmHg) (1 mmHg =
1-[6-Methoxy-3-(1-propionyl)-2-(2-pyridinyl)phenyl]-1-
propanone (6c)
133.322 4 Pa). Rf 0.49 (hexane–EtOAc, 1:1). IR (KBr):
1
1682, 831. H NMR (CDCl ) : 0.88 (t, J = 7.3 Hz, 3H),
δ
3
Dark brown solid, mp 148 °C (1 mmHg) (1 mmHg =
133.322 4 Pa). Rf 0.17 (hexane–EtOAc, 1:3). IR (KBr):
1690, 1587, 1564, 1477, 1415, 1291, 1233, 1185, 1136, 830.
1H NMR (CDCl3) δ: 0.96 (t, J = 7.3 Hz, 6H), 2.41 (q, J =
7.3 Hz, 2H), 2.54 (q, J = 7.3 Hz, 2H), 3.89 (s, 3H), 6.99 (d,
J = 8.9 Hz, 1H), 7.22–7.29 (c, 2H), 7.65–7.71 (c, 2H), 8.58
(d, J = 4.6 Hz, 1H). 13C NMR (CDCl3) δ: 7.46, 8.54, 35.11,
38.21, 55.98, 110.21, 122.53, 125.05, 130.31, 132.83,
133.26, 136.06, 138.04, 149.20, 156.50, 157.32, 204.15,
207.15. MS m/z (relative intensity, %): 297 (M+, 0), 282 (1),
269 (19), 268 (100), 153 (12), 140 (11), 120 (11). Anal.
calcd. for C18H19NO3: C 72.71, H 6.44, N 4.71; found: C
72.42, H 6.43, N 4.68.
2.50 (dq, J = 17.8, 7.3 Hz, 1H), 2.63 (dq, J = 17.8, 7.3 Hz,
1H), 7.14 (d, J = 8.6 Hz, 1H), 7.30 (t, J = 7.6 Hz, 1H), 7.36–
7.38 (m, 2H), 7.52 (t, J = 7.6 Hz, 1H), 7.65 (dt, J = 8.6,
4.1 Hz, 1H), 7.76 (d, J = 5.6 Hz, 1H), 7.89–7.96 (m, 3H),
8.05 (d, J = 8.6 Hz, 1H), 8.66 (d, J = 5.6 Hz, 1H). 13C NMR
(CDCl3) δ: 8.10, 34.89, 120.44, 124.44, 126.96, 126.99,
127.04, 127.32, 127.49, 127.50, 127.92, 128.88, 129.04,
130.32, 132.43, 134.58, 135.86, 136.27, 136.47, 141.98,
159.74, 204.00. MS m/z (relative intensity, %): 311 (M+, 0),
283 (30), 282 (100), 253 (22), 252 (17), 127 (84), 113 (21),
112 (14), 100 (13). HR-MS calcd. for C22H17NO: 311.1310
(M+); found: 311.1301.
2-(1-Naphthalenyl)-3-methylpyridine (19)
1-[5-Methyl-3-(1-propionyl)-2-(2-pyridinyl)phenyl]-1-
propanone (6d)
Brown solid, mp 74–76 °C (1 mmHg) (1 mmHg =
133.322 4 Pa). Rf 0.20 (hexane–EtOAc, 1:2). IR (KBr):
White solid, mp 87 to 88 °C (1 mmHg) (1 mmHg =
133.322 4 Pa), bp 180 °C (0.7 mmHg) (1 mmHg =
133.322 4 Pa). Rf 0.49 (hexane–EtOAc, 1:1). IR (KBr):
1
1391, 803. H NMR (CDCl3) δ: 2.07 (s, 3H), 7.26 (dd, J =
1
1697, 1591, 1560, 1455, 1429, 1405, 1342, 1128, 1054. H
7.8, 4.8 Hz, 1H), 7.37–7.57 (c, 5H), 7.64 (d, J = 7.6 Hz,
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