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Organic & Biomolecular Chemistry
Page 7 of 9
DOI: 10.1039/C7OB01552F
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114.8, 48.9, 47.8, 34.4, 31.2, 28.5, 27.0, 21.9. LRMS (EI) m/z: 4-(((4-bromophenyl)thio)methyl)-6-chloro-2,4-
381.10, 179.10, 123.05, 57.10 (100). HRMS (ESI+) m/z calculated dimethylisoquinoline-1,3(2H,4H)-dione (3bg): Isolated yield =
for C23H28NO2S (M+H)+: 382.1841 found 382.1837.
79% (167.7 mg), 1H NMR (300 MHz, CDCl3) δ: 8.13 (d, J = 8.4 Hz,
1H), 7.34 (dd, J = 1.5 Hz, J = 8.4 Hz, 1H), 7.24 (d, J = 8.4 Hz, 2H),
4-(((4-chlorophenyl)thio)methyl)-2,4,6-trimethylisoquinoline-
1,3(2H,4H)-dione (3bc): Isolated yield = 76% (136.7 mg), 1H NMR 7.16 (d, J = 1.6 Hz, 1H), 6.93 (d, J = 8.4 Hz, 2H), 3.80 (d, J = 13.2
Hz, 1H), 3.36 (d, J = 13.2 Hz, 1H), 3.26 (s, 3H), 1.67 (s, 3H). 13C
(300 MHz, CDCl3) δ: 8.09 (d, J = 7.9 Hz, 1H), 7.25-7.15 (m, 1H),
NMR (75 MHz, CDCl3) δ: 174.5, 163.4, 142.9, 140.4, 133.6, 132.7,
131.9, 130.3, 128.9, 126.0, 124.0, 121.4, 49.18, 47.51, 28.40, 27.27.
LRMS (EI) m/z: 424.85, 422.85, 202.85, 200.85, 122.05 (100),
108.00, 45.00. HRMS (ESI+) m/z calculated for C18H16BrClNO2S
(M+H)+: 423.9774 found 423.9770.
7.06 (d, J = 8.5 Hz, 2H), 7.02-6.84 (m, 3H), 3.80 (d, J = 13.2 Hz,
1H), 3.38 (d, J = 13.3 Hz, 1H), 3.27 (s, 3H), 2.28 (s, 3H), 1.64 (s,
3H). 13C NMR (75 MHz, CDCl3) δ: 175.3, 164.2, 144.6, 141.2,
133.6, 133.0, 132.6, 132.4, 128.8, 128.7, 126.0, 122.9, 49.0, 47.7,
28.7, 27.1, 21.7. LRMS (EI) m/z: 358.95, 157.00 (100), 45.00.
HRMS (ESI+) m/z calculated for C19H19ClNO2S (M+H)+: 360.0825
found 360.0821.
6-fluoro-2,4-dimethyl-4-((phenylthio)methyl)isoquinoline-
1,3(2H,4H)-dione (3bh): Isolated yield = 75% (123.5 mg), 1H NMR
(300 MHz, CDCl3) δ: 8.23 (dd, J = 2.1 Hz, J = 6.1 Hz, 1H), 7.13-
7.03 (m, 6H), 6.92 (dd, J = 2.1 Hz, J = 9.0 Hz, 1H), 3.84 (d, J = 12.9
6-methoxy-2,4-dimethyl-4-((phenylthio)methyl)isoquinoline-
1,3(2H,4H)-dione (3bd): Isolated yield = 82% (139.9 mg), 1H NMR
(300 MHz, CDCl3) δ: 8.17 (d, J = 8.8 Hz, 1H), 7.12 (br, 5H), 6.87
(dd, J = 2.1 Hz, J = 8.8 Hz, 1H), 6.66 (d, J = 2.1 Hz, 1H), 3.86 (d, J
= 13.2 Hz, 1H), 3.76 (s, 3H), 3.37 (d, J = 13.2 Hz, 1H), 3.22 (s, 3H),
1.66 (s, 3H). 13C NMR (75 MHz, CDCl3) δ: 175.3, 163.9, 143.7,
135.0, 131.2, 131.0, 128.7, 126.8, 118.5, 113.6, 110.7, 55.4, 49.1,
47.6, 28.6, 27.0. LRMS (EI) m/z: 341.05, 123.05 (100), 103.00,
77.05, 45.00. HRMS (ESI+) m/z calculated for C19H20NO3S (M+H)+:
342.1164 found 342.1160.
Hz, 1H), 3.34 (d, J = 12.9 Hz, 1H), 3.22 (s, 3H), 1.68 (s, 3H). 13
C
NMR (75 MHz, CDCl3) δ: 174.7, 167.8, 164.4, 163.4, 144.6, 134.4,
131.8, 131.1, 128.8, 127.1, 115.7, 112.6, 49.2, 47.6, 28.3, 27.1.
LRMS (EI) m/z: 329.05, 123.05 (100), 109.00, 77.05, 45.00. HRMS
(ESI+) m/z calculated for C18H17FNO2S (M+H)+: 330.0964 found
330.0960.
2,4-dimethyl-1,3-dioxo-4-((phenylthio)methyl)-1,2,3,4-
tetrahydroisoquinoline-6-carbonitrile (3bi): Isolated yield = 72%
(121.1 mg), 1H NMR (300 MHz, CDCl3) δ: 8.30 (d, J = 8.1 Hz, 1H),
7.56 (dd, J = 0.9 Hz, J = 9.0 Hz, 1H), 7.47 (s, 1H), 7.14-7.12 (m,
3H), 7.04-7.02 (m, 2H), 3.87 (d, J = 13.5 Hz, 1H), 3.38 (d, J = 13.4
Hz, 1H), 3.26 (s, 3H), 1.70 (s, 3H). 13C NMR (75 MHz, CDCl3) δ:
174.1, 162.8, 162.87, 142.3, 134.1, 131.2, 130.8, 130.1, 129.4,
129.0, 128.8, 127.5, 117.4, 117.0, 49.2, 47.6, 28.1, 27.5, 27.4. LRMS
(EI) m/z: 336.05, 123.00 (100), 109.00, 77.05, 45.00. HRMS (ESI+)
m/z calculated for C19H17N2O2S (M+H)+: 337.1011 found 337.1007.
2,4-dimethyl-4-((phenylthio)methyl)-6-
6-chloro-2,4-dimethyl-4-((phenylthio)methyl)isoquinoline-
1,3(2H,4H)-dione (3be): Isolated yield = 76% (131.4 mg), 1H NMR
(300 MHz, CDCl3) δ: 8.14 (d, J = 8.4 Hz, 1H), 7.38-7.28 (m, 1H),
7.20 (d, J = 1.4 Hz, 1H), 7.17-7.03 (m, 4H), 3.83 (d, J = 13.4 Hz,
1H), 3.36 (d, J = 13.4 Hz, 1H), 3.22 (s, 3H), 1.67 (s, 3H). 13C NMR
(75 MHz, CDCl3) δ: 174.6, 163.5, 143.1, 140.3, 134.3, 131.1, 130.2,
128.8, 128.4, 127.2, 126.0, 124.0, 49.1, 47.5, 28.2, 27.2. LRMS (EI)
m/z: 344.95, 123.95 (100), 77.00, 45.00. HRMS (ESI+) m/z
calculated for C18H17ClNO2S (M+H)+: 346.0669 found 346.0665.
6-chloro-4-(((4-methoxyphenyl)thio)methyl)-2,4-
(trifluoromethyl)isoquinoline-1,3(2H,4H)-dione (3bj): Isolated
yield = 70% (132.7 mg), 1H NMR (300 MHz, CDCl3) δ: 8.33 (d, J =
8.1 Hz, 1H), 7.58 (d, J = 8.1 Hz, 1H), 7.44 (s, 1H), 7.10-7.02 (m,
5H), 3.87 (d, J = 13.8 Hz, 1H), 3.40 (d, J = 13.8 Hz, 1H), 3.27 (s,
3H), 1.72 (s, 3H). 13C NMR (75 MHz, CDCl3) δ: 174.5, 163.2,
142.2, 135.16, 134.2, 131.1, 129.5, 128.9, 128.4, 127.2, 124.6,
122.8, 121.44, 49.3, 47.8, 28.0, 27.3. LRMS (EI) m/z: 378.95,
122.95 (100), 77.00, 45.00. HRMS (ESI+) m/z calculated for
C19H17F3NO2S (M+H)+: 380.0932 found 380.0928.
dimethylisoquinoline-1,3(2H,4H)-dione (3bf): Isolated yield =
72% (135.2 mg), 1H NMR (300 MHz, CDCl3) δ: 8.15 (d, J = 8.4 Hz,
1H), 7.32 (dd, J = 1.8 Hz, J = 8.4 Hz, 1H), 7.14 (d, J = 1.6 Hz, 1H),
6.99 (d, J = 8.7 Hz, 2H), 6.65 (d, J = 8.7 Hz, 2H), 3.80 (d, J = 13.1
Hz, 1H), 3.75 (s, 3H), 3.30 (d, J = 13.1 Hz, 1H), 3.26 (s, 3H), 1.63
(s, 3H). 13C NMR (75 MHz, CDCl3) δ: 174.7, 163.5, 159.2, 143.3,
140.3, 134.0, 130.2, 128.3, 126.1, 124.8, 124.0, 114.5, 55.3, 49.3,
48.6, 28.7, 28.7, 27.2. LRMS (EI) m/z: 374.95, 153.05 (100),
137.95, 109.05, 77.05, 45.00. HRMS (ESI+) m/z calculated for
C19H19ClNO3S (M+H)+: 376.0774 found 376.0770.
7-fluoro-2,4-dimethyl-4-((phenylthio)methyl)isoquinoline-
1
1,3(2H,4H)-dione (3bk): Isolated yield = 38% (62.5mg), H NMR
(300 MHz, CDCl3) δ: 7.87 (dd, J = 2.4 Hz, J = 9.0 Hz, 1H), 7.29-
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