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The Journal of Organic Chemistry
3.82 (s, 1H), 3.69ꢀ3.58 (m, 1H), 3.57–3.44 (m, 1H), 3.16 (s, 1H), 3.00 (s, 1H), 1.52 (s, 6H), 1.25 (s, 6H); 13C NMR (101
MHz,CDCl3) δ 167.1, 164.6, 163.8, 140.1, 134.0, 129.7, 127.8, 127.6, 127.5, 51.1, 45.7, 41.1, 27.8, 20.2, 19.9; HRMS Calcd
for C17H22N2O3Na [M+Na+]: 325.1528; Found: 325.1535.
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N,N-diisopropyl-2-(5-methyl-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoacetamide
(2b).
Purified
by
column
8
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chromatography on silica gel with petroleum ester/ethyl acetate (8/1) as an eluent; Yield 90% (56.9 mg); pale yellow solid;
mp = 159–161 °C; 1H NMR (400 MHz, CDCl3) δ 8.01 (d, J = 7.8 Hz, 1H), 7.40 (d, J = 7.4 Hz, 1H), 7.27 (t, J = 7.7 Hz, 1H),
4.36 (s, 1H), 3.79 (s, 1H), 3.68–3.61 (m, 1H), 3.56–3.49 (m, 1H), 3.00 (d, J = 5.2 Hz, 2H), 2.33 (s, 3H), 1.53 (s, 6H), 1.26 (s,
6H); 13C NMR (101 MHz, CDCl3) δ 167.0, 164.8, 163.8, 138.6, 135.4, 135.3, 127.9, 127.6, 126.9, 51.1, 45.7, 40.4, 24.7,
20.2, 19.9, 19.1; HRMS Calcd for C18H24N2O3Na [M+Na+]: 339.1685; Found: 339.1684.
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N,N-diisopropyl-2-(5-methoxy-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoacetamideo) (2c). Purified by column
chromatography on silica gel with petroleum ester/ethyl acetate (7/1) as an eluent; Yield 74% (49.2 mg); pale yellow solid;
mp = 142–145 °C; 1H NMR (400 MHz, CDCl3) δ 7.74 (d, J = 7.7 Hz, 1H), 7.32 (t, J = 8.0 Hz, 1H), 7.06 (d, J = 8.0 Hz, 1H),
4.33 (s, 1H), 3.87 (s, 3H), 3.78 (s, 1H), 3.66–3.60 (m, 1H), 3.55–3.48 (m, 1H), 3.08 (s, 1H), 3.01 (s, 1H), 1.53 (s, 6H), 1.25
(d, J = 3.5 Hz, 6H); 13C NMR (101 MHz, CDCl3) δ 167.1, 164.6, 163.8, 155.8, 129.0, 127.8, 121.3, 115.10, 55.9, 51.1, 45.7,
40.7, 21.2; HRMS Calcd for C18H24N2O4Na [M+Na+]: 355.1634; Found: 355.1641.
2-(6,7-dimethoxy-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)-N,N-diisopropyl-2-oxoacetamide (2d). Purified by column
chromatography on silica gel with petroleum ester/ethyl acetate (4/1) as an eluent; Yield 70% (50.68 mg); pale yellow solid;
mp = 179–182 °C; 1H NMR (400 MHz, CDCl3) δ 7.55 (s, 1H), 6.66 (s, 1H), 4.35 (s, 1H), 3.91 (d, J = 9.8 Hz, 6H), 3.75 (d, J
= 9.1 Hz, 1H), 3.61–3,61 (m, 1H), 3.55–3.48 (m, 1H), 3.11 (s, 1H), 2.89 (s, 1H), 1.54 (s, 3H), 1.51 (s, 3H),1.24 (m, 6H); 13
C
NMR (101 MHz, CDCl3) δ 167.0, 164.2, 163.9, 153.8, 148.4, 134.8, 120.0, 111.2, 109.5, 56.3, 51.1, 45.7, 41.3, 27.5, 20.5,
20.3, 19.9, 19.7; HRMS Calcd for C19H26N2O5Na [M+Na+]: 385.1739; Found: 385.1730.
N,N-diisopropyl-2-oxo-2-(5-oxo-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-6(5H)-yl)acetamide (2e). Purified by column
chromatography on silica gel with petroleum ester/ethyl acetate (5/1) as an eluent; Yield 78% (53.9 mg); pale yellow solid;
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mp = 168–169 °C; H NMR (400 MHz, CDCl3) δ 7.53 (s, 1H), 6.67 (s, 1H), 6.03 (s, 2H), 4.34 (s, 1H), 3.75 (s, 1H),
3.66ꢀ3.59 (m, 1H), 3.54–3.57 (m, 1H), 3.08 (s, 1H), 2.99–2.80 (m, 1H), 1.52 (s, 6H), 1.24 (d, J = 14.9 Hz, 6H); 13C NMR
(101 MHz, CDCl3) δ 167.1, 163.9, 152.6, 147.5, 136.9, 121.7, 108.9, 107.3, 102.1, 51.1, 45.7, 41.1, 28.0, 20.3, 20.1, 19.8,
19.6, 20.1; HRMS Calcd for C18H22N2O5Na [M+Na+]: 369.1429; Found: 369.1453.
2-(6,7-dimethyl-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)-N,N-diisopropyl-2-oxoacetamide (2f). Purified by column
chromatography on silica gel with petroleum ester/ethyl acetate (8/1) as an eluent; Yield 80% (52.8 mg); pale yellow solid;
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mp = 174–175 °C; H NMR (400 MHz, CDCl3) δ 7.88 (s, 1H), 7.01 (s, 1H), 4.32 (s, 1H), 3.77 (s, 1H), 3.66–3.59 (m, 1H),
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