10.1002/adsc.201800734
Advanced Synthesis & Catalysis
ethane-1,1,2-tricarboxylate (4l): 25.6 mg, 49%; 1H NMR
(400 MHz, CDCl3): δ 8.87 (d, 1H, J = 8.7 Hz) δ 8.79 (d,
1H, J = 1.5 Hz) δ 8.31 (dd, 1H, J = 1.5, 8.7 Hz) δ 5.81 (d,
1H, J = 9.7 Hz) δ 4.76 (d, 1H, J = 9.7 Hz) δ 4.33 (q, 2H, J
= 7.1 Hz) δ 4.09-4.00 (m, 5H) δ 3.66 (s, 3H) δ 3.26 (s, 3H)
δ 1.36 (t, 3H, J = 7.1 Hz) δ 1.10 (t, 3H, J = 7.1 Hz); 13C
NMR (100 MHz, CDCl3): δ 169.9, 167.8, 167.6, 167.5,
167.4, 166.0, 152.9, 150.4, 136.3, 133.6, 131.9, 129.0,
125.2, 124.0, 123.2, 61.9, 61.8, 52.82, 52.80, 48.1, 24.2,
14.1, 13.8; HRMS (ESI-TOF) m/z calcd. for
C24H24N2NaO10 ([M+Na]+) 523.1323, found 523.1325.
NMR (400 MHz, CDCl3): δ 8.84 (ddd, J = 8.3, 1.3, 0.5 Hz,
1H), δ 8.10 (d, J = 8.2 Hz, 1H), δ 7.85 (ddd, J = 8.5, 6.9,
1.5 Hz, 1H), δ 7.72 (ddd, J = 8.3, 6.9, 1.2 Hz, 1H), δ 5.77
(d, J = 9.5 Hz, 1H), δ 4.73 (d, J = 9.5 Hz, 1H), δ 4.32 (q, J
= 6.9 Hz, 1H), δ 4.04 (qq, J = 7.0, 3.7 Hz, 1H), δ 3.64 (s,
3H), δ 1.34 (t, J = 7.1 Hz, 2H), δ 1.09 (t, J = 7.1 Hz, 2H), δ
1.01 (s, 9H), δ 0.57 (s, 6H); 13C NMR (100 MHz, CDCl3):
δ 173.4, 172.8, 170.16, 167.9, 167.59, 151.8, 150.7, 137.8,
132.3, 129.7, 129.5, 125.0, 121.1, 115.9, 61.7, 61.6, 52.7,
52.6, 48.2, 26.2, 25.2, 14.0, 13.8, -4.23; HRMS (ESI-TOF)
m/z calcd. for C27H34N2NaO8Si ([M+Na]+) 565.1977,
found 565.1980.
2-tert-butyl
1,1-diethyl
2-(2-methyl-1,3-dioxo-2,3-
dihydro-1H-pyrrolo[3,4-c] quinolin-4-yl) ethane-1,1,2-
1,1-diethyl 2-methyl 2-(1,3-dioxo-2-phenyl-2,3-dihydro-
1
tricarboxylate (4m): 29.9 mg, 59%; H NMR (400 MHz,
1H-pyrrolo[3,4-c]
quinolin-4-yl)
ethane-1,1,2-
1
CDCl3): δ 8.80 (d, 1H, J = 8.4 Hz) δ 8.07 (d, 1H, J = 8.5
Hz) δ 7.85 (ddd, 1H, J = 1.4 Hz, 7.4 Hz, 8.5 Hz) δ 7.72 (m,
1H) δ 5.64 (d, 1H, J = 9.1 Hz) δ 4.66 (d, 1H, J = 9.1 Hz) δ
4.32 (m, 2H) δ 4.04 (pd, J = 3.7 Hz, 6.9 Hz) δ 3.23 (s, 3H)
δ 1.37 – 1.32 (m, 12H) δ 1.10 (t, 3H, J = 7.1 Hz); 13C NMR
(100 MHz, CDCl3): δ 168.4, 168.1, 167.9, 167.8, 167.7,
152.3, 150.8, 136.1, 134.1, 132.4, 129.7, 124.8, 122.7,
120.8, 82.5, 61.59, 61.58, 52.6, 49.2, 27.7, 24.0, 14.1, 13.8;
HRMS (ESI-TOF) m/z calcd. for C25H28N2NaO8
([M+Na]+) 507.1738, found 507.1741.
tricarboxylate (4r): 38.5 mg, 73%; H NMR (400 MHz,
CDCl3): δ 8.89 (d, 1H, J = 8.3 Hz) δ 8.14 (d, 1H, J = 8.5
Hz) δ 7.91 (ddd, 1H, J = 1.4 Hz, 7.0 Hz, 8.4 Hz) δ 7.77 (m,
1H) δ 7.57 – 7.32 (m, 5H) δ 5.85 (d, 1H, J = 9.5 Hz) δ 4.78
(d, 1H, J = 9.5 Hz) δ 4.32 (qd, 2H, J = 1.6 Hz, 7.1 Hz) δ
4.06 (qd, 2H, J = 3.0 Hz, 7.1 Hz) δ 3.67 (s, 3H) δ 1.34 (t,
3H, J = 7.1 Hz) δ 1.11 (t, 3H, J = 7.1 Hz); 13C NMR (100
MHz, CDCl3): δ 170.0, 167.9, 167.6, 166.9, 166.6, 152.0,
151.1, 135.8, 134.1, 132.8, 131.1, 129.9, 129.1, 128.3,
127.9, 126.5, 126.0, 125.0, 121.9, 121.0, 61.8, 61.7, 52.8,
52.7, 48.2, 14.0, 13.8; HRMS (ESI-TOF) m/z calcd. for
C27H24N2NaO8 ([M+Na]+) 527.1425, found 527.1425.
1,1-diethyl 2-methyl 2-(2-benzyl-1,3-dioxo-2,3-dihydro-
1H-pyrrolo[3,4-c]
quinolin-4-yl)
ethane-1,1,2-
1
tricarboxylate (4n): 47.1 mg, 87%; H NMR (400 MHz,
CDCl3): δ 8.81 (dd, 1H, J = 0.7 Hz, 8.4 Hz) δ 8.09 (d, 1H,
J = 8.5 Hz) δ 7.86 (ddd, 1H, J = 1.4 Hz, 6.9 Hz, 8.5 Hz) δ
7.73 (ddd, 1H, J = 1.1 Hz, 7.0 Hz, 8.2 Hz) δ 7.47 (d, 2H, J
= 6.9 Hz) δ 7.39 – 7.28 (m, 3H) δ 5.79 (d, 1H, J = 9.7 Hz)
δ 4.90 (d, 2H, J = 3.3 Hz) δ 4.73 (d, 1H, J = 9.7 Hz) δ 4.32
(qd, 2H, J = 1.3 Hz, 7.1 Hz) δ 3.98 (qd, 2H, J = 2.2 Hz, 7.1
Hz) δ 3.63 (s, 3H) δ 1.34 (t, 3H, J = 7.1 Hz) δ 1.03 (t, 3H, J
= 7.1 Hz); 13C NMR (100 MHz, CDCl3): δ 170.0, 167.9,
167.6, 167.4, 167.3, 151.6, 151.0, 136.2, 135.9, 132.6,
129.8, 129.7, 128.75, 128.71, 128.0, 124.8, 122.4, 121.0,
61.8, 61.6, 52.8, 52.6, 48.1, 41.8, 14.0, 13.8; HRMS (ESI-
TOF) m/z calcd. for C28H26N2NaO8 ([M+Na]+) 541.1581,
found 541.1582.
1,1-diethyl 2-methyl 2-(2-(4-methoxyphenyl)-1,3-dioxo-
2,3-dihydro-1H-pyrrolo[3,4-c]quinolin-4-yl)ethane-
1
1,1,2-tricarboxylate (4s): 41.8 mg, 75%; H NMR (400
MHz, CDCl3): δ 8.88 (d, J = 8.4 Hz, 1H), δ 8.13 (d, J = 8.6
Hz, 1H), δ 7.90 (ddt, J = 8.3, 6.9, 1.3 Hz, 1H), δ 7.77 (ddt,
J = 8.4, 6.9, 1.4 Hz, 1H), δ 7.40 (d, J = 8.7 Hz, 1H), δ 7.04
(d, J = 9.1 Hz, 1H), δ 5.84 (d, J = 9.5 Hz, 1H), δ 4.78 (d, J
= 9.5 Hz, 1H), δ 4.32 (qd, J = 7.1, 1.6 Hz, 2H), δ 4.05 (qd,
J = 7.1, 2.4 Hz, 2H), δ 3.86 (s, 3H), δ 3.66 (s, 3H), δ 1.34 (t,
J = 7.1 Hz, 2H), δ 1.11 (t, J = 7.1 Hz, 2H); 13C NMR (100
MHz, CDCl3): δ 170.09, 167.9, 167.1, 166.8, 159.3, 151.9,
151.0, 135.9, 132.78, 129.8, 127.9, 125.0, 123.7, 122.0,
121.08, 114.4, 61.79, 61.70, 55.52, 52.8, 52.7, 48.2, 14.07,
13.87; HRMS (ESI-TOF) m/z calcd. for C28H26N2NaO9
([M+Na]+) 557.1531, found 557.1533.
1,1-diethyl 2-methyl 2-(2-cyclohexyl-1,3-dioxo-2,3-
dihydro-1H-pyrrolo[3,4-c] quinolin-4-yl) ethane-1,1,2-
1,1-diethyl 2-methyl 2-(2-(4-(methoxycarbonyl)phenyl)-
1,3-dioxo-2,3-dihydro-1H-pyrrolo[3,4-c]quinolin-4-
yl)ethane-1,1,2-tricarboxylate (4t): 36.7 mg, 63%; 1H
NMR (400 MHz, CDCl3): δ 8.89 (d, J = 8.4 Hz, 1H), δ
8.21 (d, J = 8.7 Hz, 2H), δ 8.15 (d, J = 8.5 Hz, 1H), δ 7.93
(ddd, J = 8.5, 6.9, 1.4 Hz, 1H), δ 7.80 (ddd, J = 8.2, 7.0,
1.1 Hz, 1H), δ 7.66 (d, J = 8.7 Hz, 2H), δ 5.85 (d, J = 9.6
Hz, 1H), δ 4.79 (d, J = 9.6 Hz, 1H), δ 4.33 (qd, J = 7.1, 1.7
Hz, 2H), δ 4.10 – 4.01 (m, 2H), δ 3.96 (s, 3H), δ 3.67 (s,
3H), δ 1.35 (t, J = 7.1 Hz, 3H), δ 1.11 (t, J = 7.1 Hz, 3H);
13C NMR (100 MHz, CDCl3): δ 170.0, 167.8, 167.6, 166.4,
166.2, 166.1, 152.1, 151.1, 135.6, 135.3, 133.0, 130.4,
130.1, 129.9, 129.5, 125.9, 124.9, 121.8, 121.0, 61.86,
61.77, 52.81, 52.78, 52.33, 48.21, 14.07, 13.87; HRMS
(ESI-TOF) m/z calcd. for C29H26N2NaO10 ([M+Na]+)
585.1480, found.585.1483.
1
tricarboxylate (4o): 37.9 mg, 71%; H NMR (400 MHz,
CDCl3): δ 8.81 (d, 1H, J = 7.9) δ 8.08 (d, 1H, J = 8.6 Hz) δ
7.85 (ddd, 1H, J = 1.3 Hz, 7.0 Hz, 8.5 Hz) δ 7.75 – 7.70
(m ,1H) δ 5.78 (d, 1H, J = 9.7 Hz) δ 4.74 (d, 1H, J = 9.7
Hz) δ 4.31(qd, 2H, J = 1.9 Hz, 7.1 Hz) δ 4.20 – 4.12 (m,
1H) δ 4.01 (qd, 2H, J = 3.0 Hz, 7.1 Hz) δ 2.24 (ddd, 2H, J
= 8.7 Hz, 12.8 Hz, 16.7 Hz) δ 1.89 (d, 2H, J = 13.0 Hz) δ
1.79 (d, 2H, J = 11.3 Hz) δ 1.72 (d, 1H, J = 12.1 Hz) δ 1.45
– 1.36 (m, 2H) δ 1.33 (t, 3H, J = 7.1 Hz) δ 1.07 (t, 3H, J =
7.1 Hz); 13C NMR (100 MHz, CDCl3): δ 170.1, 168.0,
167.9, 167.7, 167.5, 151.5, 150.9, 136.0, 132.4, 129.7,
129.5, 124.8, 122.1, 121.0, 61.7, 61.6, 52.8, 52.6, 51.2,
48.0, 29.9, 29.8, 26.0, 14.0, 13.8; HRMS (ESI-TOF) m/z
calcd. for C27H30N2NaO8 ([M+Na]+) 533.1894, found
533.1896.
1,1-diethyl
2-methyl
2-(1,3-dioxo-2,3-dihydro-1H-
1,1-diethyl 2-methyl 2-(2-(benzyloxy)-1,3-dioxo-2,3-
dihydro-1H-pyrrolo[3,4-c]quinolin-4-yl)ethane-1,1,2-
pyrrolo[3,4-c] quinolin-4-yl) ethane-1,1,2-tricarboxylate
1
1
(4p): 25.3 mg, 56%; H NMR (400 MHz, CDCl3): δ 8.81
tricarboxylate (4u): 41.7 mg, 78%; H NMR (400 MHz,
(ddd, 1H, J = 0.6 Hz, 1.4 Hz, 8.4 Hz) δ 8.14 – 8.10 (m, 1H)
δ 7.89 (ddd, 1H, 1.5 Hz, 6.9 Hz, 8.5 Hz) δ 7.76 (ddd, 1H, J
= 1.2 Hz, 6.9 Hz, 8.2 Hz) δ 5.77 (d, 1H, J = 9.7 Hz) δ 4.77
(d, 1H, J = 9.7 Hz) δ 4.33 (qd, 2H, J = 0.8 Hz, 7.1 Hz) δ
4.07 – 4.00 (m, 2H) δ 3.66 (s, 3H) δ 1.35 (t, 3H, J = 7.1
Hz) δ 1.09 (t, 3H, J = 7.1 Hz); 13C NMR (100 MHz,
CDCl3): δ 170.0, 167.9, 167.5, 167.4, 167.0, 152.0, 151.0,
136.6, 135.1, 132.8, 129.9, 124.8, 122.9, 121.1, 61.8, 61.7,
52.8, 52.7, 48.1, 14.0, 13.8; HRMS (ESI-TOF) m/z calcd.
for C21H20N2NaO8 ([M+Na]+) 451.1112, found 451.1112.
CDCl3): δ 8.75 (d, J = 7.8 Hz, 1H), δ 8.08 (d, J = 8.5 Hz,
1H), δ 7.91 – 7.85 (m, 1H), δ 7.74 (ddd, J = 8.2, 6.9, 1.2
Hz, 1H), δ 7.60 – 7.54 (m, 2H), δ 7.39 (m, 3H), δ 5.71 (d, J
= 9.6 Hz, 1H), δ 5.27 (s, 2H), δ 4.74 (d, J = 9.6 Hz, 1H), δ
4.32 (q, J = 6.4 Hz, 2H), δ 4.03 (qd, J = 7.1, 5.7 Hz, 2H), δ
3.64 (s, 3H), δ 1.35 (t, J = 7.1 Hz, 3H), δ 1.08 (t, J = 7.1
Hz, 3H); 13C NMR (100 MHz, CDCl3): δ 169.8, 167.8,
167.4, 163.2, 163.0, 151.4, 151.1, 133.5, 132.99, 132.98,
131.6, 129.96, 129.96, 129.91, 129.8, 129.4, 128.6, 124.8,
120.5, 119.1, 80.1, 61.8, 61.7, 52.75, 52.73, 48.1, 14.0,
13.8; HRMS (ESI-TOF) m/z calcd. for C28H26N2NaO9
([M+H]+) 535.1711, found 535.1708.
1,1-diethyl 2-methyl 2-(2-(tert-butyldimethylsilyl)-1,3-
dioxo-2,3-dihydro-1H-pyrrolo[3,4-c]quinolin-4-
1
yl)ethane-1,1,2-tricarboxylate (4q): 18.1 mg, 32%; H
7
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