Page 11 of 14
The Journal of Organic Chemistry
(CDCl3, 100 MHz) δ 165.1, 143.1, 132.6, 131.7, 130.5, 129.8, Cyclohexyl(4-methoxyphenyl)sulfane (6b). This compound
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128.8, 127.5, 127.0, 125.3, 124.9, 122.8, 121.6, 43.1, 42.1, 37.2,
29.3. HRMS (ESI-TOF) m/z: [M+H] calcd for C23H23NCl
348.1519, found 348.1512.
was prepared by the general procedure 2, 37.8mg, 85%, 3 h,
15.1 mg, 34%, 6 h, colorless oil; 1H NMR (CDCl3, 400 MHz) δ
7.39-7.37 (m, 2H), 6.85-6.83 (m, 2H), 3.80 (s, 3H), 2.93-2.87
(m, 1H), 1.94-1.92 (m, 2H), 1.76-1.74 (m, 2H), 1.60-1.57 (m,
1H), 1.35-1.20 (m, 5H); 13C{1H} NMR (CDCl3, 100 MHz) δ
159.4, 135.7, 125.1, 114.4, 55.4, 48.0, 33.5, 26.2, 25.9.32
6-Adamantanyl-2-fluoro-4-methylphenanthridine (4i). This
compound was prepared by the general procedure 1, 66.5 mg,
77%, 6 h, white solid, m.p. 214-216 oC; 1H NMR (CDCl3, 400
MHz) δ 8.84 (d, J = 8.5 Hz, 1H), 8.54 (d, J = 8.5 Hz, 1H), 7.96
(dd, J1 = 10.3 Hz, J2 = 2.4 Hz, 1H), 7.75 (t, J = 7.6 Hz, 1H),
7.65 (t, J = 7.7 Hz, 1H), 7.31 (dd, J1 = 9.1 Hz, J2 = 1.9 Hz, 1H),
2.86 (s, 3H), 2.47 (m, 6H), 2.23 (brs, 3H), 1.95-1.87 (m, 6H);
13C{1H} NMR (CDCl3, 100 MHz) δ 163.6 (d, J = 3.0 Hz), 162.0,
159.6, 161.6 (d, J = 8.8 Hz), 138.5, 134.0 (d, J = 4.4 Hz), 129.1,
128.0, 126.2, 124.5, 124.3 (d, J = 9.5 Hz), 123.7, 117.7 (d, J =
23.3 Hz), 104.1 (d, J = 22.6 Hz), 43.7, 42.2, 37.4, 29.4, 18.5.
HRMS (ESI-TOF) m/z: [M+H] calcd for C24H25NF 346.1971,
found 346.1969.
tert-Butyl(p-tolyl)sulfane (6c). This compound was prepared
by the general procedure 2, 29.9mg, 83%, 1 h; This compound
was prepared by the general procedure 3, 33.5 mg, 93%, 7 h,
colorless oil; 1H NMR (CDCl3, 400 MHz) δ 7.43-7.41 (m, 2H),
7.15-7.13 (m, 2H), 2.36 (s, 3H), 1.28 (s, 9H); 13C{1H} NMR
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(CDCl3, 100 MHz) δ 138.9, 137.6, 129.4, 129.3, 45.7, 31.0, 21.4.
31
Cyclohexyl(p-tolyl)sulfane (6d). This compound was
prepared by the general procedure 2, 30.5mg, 74%, 2 h,
colorless oil; 1H NMR (CDCl3, 400 MHz) δ 7.33-7.31 (m, 2H),
7.12-7.09 (m, 2H), 3.05-2.99 (m, 1H), 2.33 (s, 3H), 1.98-1.95
(m, 2H), 1.78-1.75 (m, 2H), 1.63-1.60 (m, 1H), 1.40-1.21 (m,
5H); 13C{1H} NMR (CDCl3, 100 MHz) δ 137.0, 132.9, 131.3,
129.6, 47.2, 33.5, 26.2, 25.9, 21.2. 32
6-Cyclohexyl-8-phenylphenanthridine (4j). This compound
was prepared by the general procedure 1, 71.6 mg, 85%, 6 h,
o
1
white solid, m.p. 100-101 C; H NMR (CDCl3, 400 MHz) δ
8.62 (d, J = 8.6 Hz, 1H), 8.48 (d, J = 7.5 Hz, 1H), 8.44 (d, J =
1.6 Hz, 1H), 8.13 (dd, J1 = 8.1 Hz, J2 = 0.9 Hz 1H), 7.98 (dd, J1
= 8.6 Hz, J2 = 1.8 Hz, 1H), 7.72-7.71 (m, 2H), 7.70-7.66 (m,
1H), 7.59-7.55 (m, 1H), 7.54-7.50 (m, 2H), 7.44-7.40 (m, 1H),
3.66 (tt, J1 = 11.4 Hz, J2 = 3.1 Hz, 1H), 2.11-2.08 (m, 2H), 1.97-
1.95 (m, 4H), 1.85-1.82 (m, 1H), 1.62-1.52 (m, 2H),1.47-1.41
(m, 1H); 13C{1H} NMR (CDCl3, 100 MHz) δ 165.5, 143.9,
140.9, 140.0, 132.1, 130.0, 129.3, 129.2, 128.5, 127.9, 127.6,
126.3, 125.1, 123.8, 123.3, 123.3, 122.0, 42.1, 32.4, 27.0, 126.4.
HRMS (ESI-TOF) m/z: [M+H] calcd for C25H24N 338.1909,
found 338.1901.
tert-Butyl(phenyl)sulfane (6e). This compound was prepared
by the general procedure 2, 27.2mg, 82%, 0.5 h; This compound
was prepared by the general procedure 3, 30.9 mg, 93%, 2 h,
colorless oil; 1H NMR (CDCl3, 400 MHz) δ 7.55-7.53 (m, 2H),
7.37-7.33 (m, 3H), 1.29 (s, 9H); 13C{1H} NMR (CDCl3, 100
MHz) δ 137.6, 132.8, 128.8, 128.6, 46.0, 31.1. 32
Cyclohexyl(phenyl)sulfane (6f). This compound was
prepared by the general procedure 2, 31.6mg, 82%, 1 h,
colorless oil; 1H NMR (CDCl3, 400 MHz) δ 7.41-7.38 (m, 2H),
7.29-7.25 (m, 2H), 7.25-7.18(m, 1H), 3.14-3.06 (M, 1h), 2.00-
1.97 (m, 2H), 1.78-1.76 (m, 2H), 1.63-1.60 (m, 1H), 1.39-1.25
(m, 5H); 13C{1H} NMR (CDCl3, 100 MHz) δ 135.3, 132.0,
128.9, 126.7, 46.7, 33.5, 26.2, 25.9. 32
6-Cyclohexylphenanthridine (4k). This compound was
prepared by the general procedure 1, 52.3 mg, 80%, 6 h, yellow
oil; 1H NMR (CDCl3, 400 MHz) δ 8.64 (d, J = 8.2 Hz, 1H), 8.53
(dd, J1 = 8.2 Hz, J2 = 1.3 Hz, 1H), 8.32 (d, J = 8.3 Hz, 1H), 8.18
(dd, J1 = 8.1 Hz, J2 = 0.9 Hz, 1H) 7.82-7.78 (m, 1H), 7.74-7.66
(m, 2H), 7.63-7.59 (m, 1H), 3.64 (tt, J1 = 11.4 Hz, J2 = 3.3 Hz,
1H), 2.13-2.10 (m, 2H), 2.03-1.86 (m, 5H), 1.65-1.55 (m, 2H),
1.52-1.45 (m, 1H);13C{1H} NMR (CDCl3, 100 MHz) δ 165.4,
144.0, 133.1, 130.0, 130.0, 128.5, 127.1, 126.2, 125.7, 124.8,
123.4, 122.6, 121.9, 42.1, 32.4, 27.0, 26.4. HRMS (ESI-TOF)
m/z: [M+H] calcd for C19H20N 262.1596, found 262.1593.30
tert-Butyl(4-chlorophenyl)sulfane (6g). This compound was
prepared by the general procedure 2, 36.5mg, 91%, 10 min;
This compound was prepared by the general procedure 3, 36.9
mg, 92%, 2 h, colorless oil; 1H NMR (CDCl3, 400 MHz) δ 7.46-
7.44 (m, 2H), 7.31-7.29 (m, 2H), 1.27 (s, 9H); 13C{1H} NMR
(CDCl3, 100 MHz) δ 138.8, 135.3, 131.4, 128.8, 46.3, 31.0.33
(4-Chlorophenyl)(cyclohexyl)sulfane (6h). This compound
was prepared by the general procedure 2, 39.5mg, 87%, 10 min;
This compound was prepared by the general procedure 3, 41.7
mg, 92%, 3 h, colorless oil; 1H NMR (CDCl3, 400 MHz) δ 7.33-
7.31 (m, 2H), 7.26-7.24 (m, 2H), 3.06-3.05 (m, 1H), 1.97-1.94
(m, 2H), 1.78-1.76 (m, 2H), 1.63-1.59 (m, 1H), 1.34-1.29 (m,
5H); 13C{1H} NMR (CDCl3, 100 MHz) δ 133.8, 133.4, 132.8,
129.0, 47.0, 33.4, 26.1, 25.8. 32
tert-Butyl 2-(phenanthridin-6-yl)pyrrolidine-1-carboxylate
(4l). This compound was prepared by the general procedure 1,
o
1
86.1 mg, 99%, 6 h, white solid, m.p. 135-136 C; H NMR
(CDCl3, 400 MHz) δ 8.69-8.63 (m ,1H), 8.56-8.82 (m, 1H),
8.28-8.24 (m, 1H), 8.11-8.06 (m, 1H), 7.86-7.79 (m, 1H), 7.70-
7.63 (m, 3H), 5.90-5.70 (m, 1H), 3.99-3.93 (m, 1H), 3.76-3.61
(m, 1H), 2.57-2.50 (m, 1H), 2.16-1.92 (m, 3H), 1.47 (s, 3H),
0.93 (s, 6H); 13C{1H} NMR (CDCl3, 100 MHz) δ 161.3, 154.8,
143.5, 133.2, 130.5 and 130.4, 130.3 and 130.2, 128.7 and 128.4,
127.3 and 127.2, 126.6 and 126.4, 125.4 and 125.1, 124.0 and
123.7, 122.8 and 122.7, 121.9, 79.1 and 78.9, 60.2 and 59.5,
47.2 and 47.1, 33.4 and 32.3, 28.7 and 28.1, 23.8 and 23.6.
HRMS (ESI-TOF) m/z: [M+H]calcd for C22H25N2O2 349.1916,
found 349.1919.18
2-Methylisoquinolin-1(2H)-one (9a). This compound was
prepared by the general procedure 4, 23.3 mg, 73%, 12 h, light
yellow oil; 1H NMR (CDCl3, 500 MHz) δ 8.43 (d, J = 8.1 Hz,
1H), 7.62 (t, J = 7.5 Hz, 1H), 7.51-7.46 (m, 2H), 7.07 (d, J = 7.3
Hz, 1H), 6.48 (d, J = 7.3 Hz, 1H), 3.61 (s, 3H); 13C{1H} NMR
(CDCl3, 125 MHz) δ 162.7, 137.2, 132.5, 132.1, 127.7, 126.9,
126.2, 126.0, 106.1, 37.1.24
6-Bromo-2-methylisoquinolin-1(2H)-one
(9b).
This
tert-Butyl(4-methoxyphenyl)sulfane (6a). This compound
was prepared by the general procedure 2, 34.6mg, 88%, 1 h,
colorless oil; 1H NMR (CDCl3, 400 MHz) δ 7.46-7.42 (m, 2H),
6.87-6.84 (m, 2H), 3.81 (s, 3H), 1.26 (s, 9H); 13C{1H} NMR
(CDCl3, 100 MHz) δ 160.3, 139.0, 123.7, 114.1, 55.4, 45.6,
30.9.31
compound was prepared by the general procedure 4, 41.6 mg,
87%, 12 h, white solid, m.p. 152-154 oC; 1H NMR (CDCl3, 400
MHz) δ 28 (d, J = 8.6 Hz, 1H), 7.67 (d, J = 1.9 Hz, 1H), 7.57
(dd, J1 = 8.6 Hz, J2 = 1.9 Hz, 1H), 7.09 (d, J = 7.4 Hz, 1H), 6.39
(d, J = 7.3 Hz, 1H), 3.59 (s, 3H); 13C{1H} NMR (CDCl3, 100
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