1604
D. Thomae et al.
PAPER
GC-MS (EI, 70 eV): m/z = 358 [M+], 343, 330, 315, 219, 207.
9-Amino-2-(4-methylphenyl)-5,6,7,8-tetrahydroselenophe-
no[3,2-b]quinoline (4b)
Yield: 80% (Method A), 89% (Method B); colorless solid; mp 254–
256 °C.
Anal. Calcd for C18H18N2OSe: C, 60.51; H, 5.08; N, 7.84. Found: C,
60.78; H, 5.26; N, 7.94.
IR (neat): 2929 (m), 1646 (s), 1559 (s), 153 (s), 807 (s) cm–1.
10-Amino-2-(4-methoxyphenyl)-6,7,8,9-tetrahydro-5H-cyclo-
hepta[b]selenopheno[2,3-e]pyridine (5c)
Yield: 75% (Method A), 82% (Method B); colorless solid; mp 240–
242 °C.
1H NMR (250 MHz, DMSO-d6): d = 1.79 (m, 4 H, 2 × CH2), 2.34
(s, 3 H, CH3), 2.50 (m, 2 H, CH2), 2.75 (m, 2 H, CH2), 6.02 (s, 2 H,
NH2), 7.26 (d, J = 7.5 Hz, 2 H, 2 × CH), 7.58 (d, J = 7.5 Hz, 2 H,
2 × CH), 7.76 (s, 1 H, CH).
IR (neat): 2918 (m), 1650 (m), 1533 (s), 1498 (s), 825 (s) cm–1.
13C NMR (63 MHz, DMSO-d6): d = 20.75, 22.43, 22.66, 23.34,
32.67, 109.92, 116.48, 123.82, 125.85, 130.67, 132.80, 138.10,
146.73, 148.50, 154.63, 157.29.
1H NMR (250 MHz, DMSO-d6): d = 1.54 (m, 2 H, CH2), 1.56 (m,
2 H, CH2), 1.79 (m, 2 H, CH2), 2.72 (m, 2 H, CH2), 2.88 (m, 2 H,
CH2), 3.79 (s, 3 H, CH3), 5.97 (s, 2 H, NH2), 7.00 (d, J = 7.5 Hz,
2 H, 2 × CH), 7.60 (d, J = 7.5 Hz, 2 H, 2 × CH), 7.67 (s, 1 H, CH).
13C NMR (63 MHz, CDCl3): d = 26.04, 26.64, 27.29, 32.22, 39.05,
55.41, 116.50, 119.92, 123.51, 127.51, 127.76, 128.59, 146.16,
148.08, 157.06, 160.05, 162.65.
GC-MS (EI, 70 eV): m/z = 342 [M+], 326, 314, 163, 115, 91.
Anal. Calcd for C18H18N2Se: C, 63.34; H, 5.32; N, 8.21. Found: C,
63.38; H, 5.33; N, 8.35.
10-Amino-2-(4-methylphenyl)-6,7,8,9-tetrahydro-5H-cyclohep-
ta[b]selenopheno[2,3-e]pyridine (5b)
GC-MS (EI, 70 eV): m/z = 372 [M+], 357, 343, 328, 315, 300, 219,
207.
Yield: 76% (Method A), 91% (Method B); light-brown solid; mp
276–278 °C.
IR (neat): 2917 (m), 1648 (s), 1559 (s), 1534 (s), 809 (s) cm–1.
Anal. Calcd for C19H20N2OSe: C, 61.45; H, 5.43; N, 7.54. Found: C,
61.25; H, 5.53; N, 7.72.
8-Amino-2-(4-chlorophenyl)-6,7-dihydro-5H-cyclopenta[b]se-
lenopheno[2,3-e]pyridine (3d)
Yield: 84% (Method A), 94% (Method B); brown solid; mp 270–
272 °C.
1H NMR (250 MHz, DMSO-d6): d = 1.55 (m, 4 H, 2 × CH2), 1.58
(m, 2 H, CH2), 2.30 (s, 3 H, CH3), 2.72 (m, 2 H, CH2), 2.89 (m, 2 H,
CH2), 5.99 (s, 2 H, NH2), 7.25 (d, J = 7.5 Hz, 2 H, 2 × CH), 7.56 (d,
J = 7.5 Hz, 2 H, 2 × CH), 7.75 (s, 1 H, CH).
13C NMR (63 MHz, DMSO-d6): d = 20.74, 25.00, 26.47, 27.32,
31.75, 32.07, 115.20, 118.55, 124.01, 125.68, 129.66, 132.83,
138.04, 146.79, 147.58, 156.60, 161.75.
IR (neat): 2952 (m), 1642 (s), 1539 (s), 1562 (s), 814 (s) cm–1.
1H NMR (250 MHz, DMSO-d6): d = 2.04 (m, 2 H, CH2), 2.75 (m
2 H, CH2), 2.83 (m, 2 H, CH2), 6.22 (s, 2 H, NH2), 7.57 (d, J = 7.5
Hz, 2 H, 2 × CH), 7.62 (d, J = 7.5 Hz, 2 H, 2 × CH), 7.71 (s, 1 H,
CH).
13C NMR (63 MHz, DMSO-d6): d = 22.41, 27.47, 33.76, 114.67,
117.80, 125.28, 127.56, 129.08, 132.88, 134.46, 144.87, 146.83,
158.93, 164.10.
GC-MS (EI, 70 eV): m/z = 356 [M+], 341, 327, 163, 115, 91.
Anal. Calcd for C19H20N2Se: C, 64.22; H, 5.67; N, 7.88. Found: C,
64.08; H, 5.57; N, 7.98.
8-Amino-2-(4-methoxyphenyl)-6,7-dihydro-5H-cyclopen-
ta[b]selenopheno [2,3-e]pyridine (3c)
GC-MS (EI, 70 eV): m/z = 348 [M+], 331, 311, 267.
Yield: 83% (Method A), 75% (Method B); light-brown solid; mp
236–238 °C.
IR (neat): 2944 (m), 1647 (m), 1562 (s), 1540 (s), 810 (s) cm–1.
Anal. Calcd for C16H13ClN2Se: C, 55.27; H, 3.77; N, 8.06. Found:
C, 55.54; H, 3.83; N, 8.09.
9-Amino-2-(4-chlorophenyl)-5,6,7,8-tetrahydroselenophe-
no[3,2-b]quinoline (4d)
Yield: 94% (Method A), 79% (Method B); brown solid; mp 258–
1H NMR (250 MHz, CDCl3): d = 2.22 (m, 2 H, CH2), 2.82 (m, 2 H,
CH2), 3.05 (m, 2 H, CH2), 3.87 (s, 3 H, CH3), 4.18 (s, 2 H, NH2),
6.96 (d, J = 7.5 Hz, 2 H, 2 × CH), 7.64 (d, J = 7.5 Hz, 2 H, 2 × CH),
7.71 (s, 1 H, CH).
13C NMR (63 MHz, CDCl3): d = 22.96, 27.27, 34.38, 55.41, 114.36,
115.65, 123.36, 127.86, 128.63, 129.59, 145.00, 147.76, 159.85,
160.04, 165.15.
260 °C.
IR (neat): 2932 (m), 1628 (m), 1557 (s), 1528 (s), 814 (s) cm–1.
1H NMR (250 MHz, DMSO-d6): d = 1.77 (m, 4 H, 2 × CH2), 2.48
(m, 2 H, CH2), 2.74 (m, 2 H, CH2), 6.08 (s, 2 H, NH2), 7.50 (d,
J = 7.5 Hz, 2 H, 2 × CH), 7.67 (d, J = 7.5 Hz, 2 H, 2 × CH), 7.84 (s,
1 H, CH).
13C NMR (63 MHz, DMSO-d6): d = 22.37, 22.59, 23.35, 32.60,
110.16, 117.05, 125.22, 127.61, 129.09, 132.94, 134.43, 145.07,
148.63, 154.76, 156.95.
GC-MS (EI, 70 eV): m/z = 344 [M+], 329, 300, 219, 207.
Anal. Calcd for C17H16N2OSe: C, 59.48; H, 4.70; N, 8.16. Found: C,
59.61; H, 4.52; N, 8.13.
9-Amino-2-(4-methoxyphenyl)-5,6,7,8-tetrahydroselenophe-
no[3,2-b]quinoline (4c)
GC-MS (EI, 70 eV): m/z = 362 [M+], 346, 334, 281.
Yield: 73% (Method A), 84% (Method B); colorless solid; mp 246–
248 °C.
IR (neat): 2933 (m), 1646 (m), 1532 (s), 1499 (s), 822 (s) cm–1.
Anal. Calcd for C17H15ClN2Se: C, 56.45; H, 4.18; N, 7.74. Found:
C, 56.61; H, 4.16; N, 7.49.
10-Amino-2-(4-chlorophenyl)-6,7,8,9-tetrahydro-5H-cyclohep-
ta[b]selenopheno[2,3-e]pyridine (5d)
Yield: 90% (Method A), 88% (Method B); brown solid; mp 274–
276 °C.
IR (neat): 2917 (m), 1648 (m), 1559 (s), 1531 (s), 820 (s) cm–1.
1H NMR (250 MHz, DMSO-d6): d = 1.57 (m, 4 H, 2 × CH2), 1.79
(m, 2 H, CH2), 2.38 (m, 2 H, CH2), 2.89 (m, 2 H, CH2), 6.06 (s, 2 H,
1H NMR (250 MHz, CDCl3): d = 1.79 (m, 2 H, CH2), 1.81 (m, 2 H,
CH2), 2.47 (m, 2 H, CH2), 2.86 (m, 2 H, CH2), 3.73 (s, 3 H, CH3),
4.13 (s, 2 H, NH2), 6.83 (d, J = 7.5 Hz, 2 H, 2 × CH), 7.49 (d,
J = 7.5 Hz, 2 H, 2 × CH), 7.66 (s, 1 H, CH).
13C NMR (63 MHz, CDCl3): d = 22.71, 22.92, 23.38, 33.04, 55.40,
110.96, 114.35, 123.23, 127.77, 128.55, 129.59, 147.28, 147.91,
155.79, 157.80, 160.07.
Synthesis 2008, No. 10, 1600–1606 © Thieme Stuttgart · New York