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Green Chemistry
Page 7 of 10
Journal Name
DOI: 10.1039/C6GC00557H
ARTICLE
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84%); mp 164–165 C; H NMR (500 MHz, CDCl3): δ=7.80–7.84 10.97 (2s, 1H), 7.69–7.86 (m, 4H), 7.27–7.43 (m, 2H), 7.03–
(m, 2H), 7.63–7.67 (m, 2H), 6.99–7.34 (m, 3H), 4.49 and 4.85 7.07 (m, 1H), 6.95–6.99 (m, 1H), 4.55 and 4.89 (2s, 2H), 3.63
(2s, 2H), 3.59 and 3.96 (2t, 3JH–H=5.7 and 3JH–H=6.1 Hz, 2H), and 4.02 (2t, 3JH–H=4.8 and 3JH–H=5.0 Hz, 2H), 2.68 and 2.87
2.81 and 2.93 (2t, 3JH–H=5.6 and 3JH–H=5.9 Hz, 2H); 13C NMR (2t, 3JH–H=5.4 and 3JH–H=5.9 Hz, 2H); 13C NMR (125 MHz,
(125 MHz, CDCl3): δ=189.9, 189.8, 165.4, 165.0, 133.7, 133.4, DMSO-d6): δ=190.4, 190.2, 165.3, 164.8, 135.8, 135.8, 132.4,
132.9, 132.4, 132.2, 131.8, 131.7, 131.0, 130.6, 130.4, 130.4, 131.7, 131.4, 131.3, 130.9, 130.9, 129.5, 129.2, 128.9, 126.2,
130.4, 130.0, 129.4, 128.9, 120.4, 120.1, 46.8, 43.3, 43.0, 39.2, 126.1, 121.0, 120.9, 118.5, 118.5, 117.5, 117.4, 111.0, 110.9,
28.7, 27.7; HRMS (ESI-TOF) m/z Calcd for C17H13Br2NO2 [M+H]+ 106.9, 105.9, 79.0, 78.8, 78.5, 43.6, 43.3, 21.3, 20.3; HRMS
421.9391, found 421.9393.
(ESI-TOF) m/z Calcd for C19H15BrN2O2 [M+H]+ 383.0395, found
1-(7-Bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2-(3-
383.0401.
bromophenyl)ethane-1,2-dione (3u). Off-white solid (357 mg, 1-(3-Bromophenyl)-2-(1,3,4,9-tetrahydro-2H-pyrido[3,4-
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85%); mp 160–161 C; H NMR (500 MHz, CDCl3): δ=8.09–8.12 b]indol-2-yl)ethane-1,2-dione (3z). Brick red solid (271 mg,
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(m, 1H), 7.86–7.89 (m, 1H), 7.77 (s, 1H), 7.01–7.39 (m, 4H), 71%); mp 142–143 C; H NMR (500 MHz, DMSO-d6): δ=10.63
4.49 and 4.86 (2s, 2H), 3.59 and 3.96 (2s, 2H), 2.82 and 2.94 and 11.00 (2s, 1H), 7.86–8.06 (m, 3H), 7.53–7.61 (m, 1H), 7.28–
(2s, 2H); 13C NMR (125 MHz, CDCl3): δ=189.5, 189.4, 165.1, 7.44 (m, 2H), 7.04–7.08 (m, 1H), 6.96–7.00 (m, 1H), 4.58 and
164.8, 137.7, 134.7, 134.6, 133.7, 133.4, 132.9, 132.4, 132.3, 4.90 (2s, 2H), 3.65 and 4.03 (2t, 3JH–H=5.1 and 3JH–H=5.4 Hz,
132.2, 130.6, 130.5, 130.4, 130.4, 130.0, 129.4, 128.9, 128.3, 2H), 2.69 and 2.87 (2t, 3JH–H=5.4 and 3JH–H=5.9 Hz, 2H); 13C
123.3, 123.3, 120.4, 120.1, 46.8, 43.3, 43.1, 39.3, 28.7, 27.7; NMR (125 MHz, DMSO-d6): δ=190.0, 189.8, 165.1, 164.6,
HRMS (ESI-TOF) m/z Calcd for C17H13Br2NO2 [M+H]+ 421.9391, 137.7, 135.9, 134.4, 134.3, 131.6, 131.1, 131.1, 129.3, 129.1,
found 421.9393.
128.5, 128.5, 126.2, 126.2, 122.5, 121.1, 120.9, 118.6, 117.6,
117.5, 111.1, 111.0, 106.9, 106.0, 79.0, 43.7, 43.4, 21.3, 20.3;
1-(7-Bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2-(2,4-
dichlorophenyl)ethane-1,2-dione (3v). White solid (328 mg, HRMS (ESI-TOF) m/z Calcd for C19H15BrN2O2 [M+H]+ 383.0395,
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80%); mp 129–130 C; H NMR (500 MHz, CDCl3): δ=7.81–7.86 found 383.0397.
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(m, 1H), 7.19–7.46 (m, 4H), 7.02–7.06 (m, 1H), 4.64 and 4.79 1-(2,4-Dichlorophenyl)-2-(1,3,4,9-tetrahydro-2H-pyrido[3,4-
(2s, 2H), 3.71 and 3.91 (2t, 3JH–H=5.7 and 3JH–H=6.1 Hz, 2H), b]indol-2-yl)ethane-1,2-dione (3aa). Pale yellow solid (279 mg,
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2.91 (t, 3JH–H=5.7, 2H); 13C NMR (125 MHz, CDCl3): δ=188.8, 75%); mp 185–186 C; H NMR (500 MHz, DMSO-d6): δ=10.74
188.5, 165.4, 165.2, 140.4, 140.3, 134.6, 134.4, 133.7, 133.5, and 10.97 (2s, 1H), 7.79–7.92 (m, 2H), 7.62–7.67 (m, 1H), 7.31–
133.2, 133.0, 132.5, 131.9, 131.7, 130.6, 130.5, 130.4, 130.3, 7.43 (m, 2H), 6.97–7.08 (m, 2H), 4.71 and 4.82 (2s, 2H), 3.76
130.2, 130.0, 129.4, 128.9, 127.9, 120.3, 120.1, 46.9, 43.6, and 3.97 (2t, 3JH–H=4.8 and 3JH–H=5.0 Hz, 2H), 2.78 and 2.82
43.2, 39.5, 28.4, 27.2; HRMS (ESI-TOF) m/z Calcd for (2t, 3JH–H=5.4 and 3JH–H=5.9 Hz, 2H); 13C NMR (125 MHz,
C17H12BrCl2NO2 [M+H]+ 411.9506, found 411.9503.
DMSO-d6): δ=188.6, 188.5, 165.3, 164.9, 139.3, 139.3, 135.9,
1-(7-Bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2-(4-
134.1, 133.8, 133.6, 133.3, 131.2, 130.9, 130.6, 130.4, 129.2,
chlorophenyl)ethane-1,2-dione (3w). White solid (319 mg, 129.1, 128.2, 128.2, 126.2, 126.2, 121.0, 120.9, 118.5, 117.6,
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85%); mp 159–160 C; H NMR (500 MHz, CDCl3): δ=7.88–7.92 117.5, 111.0, 111.0, 106.8, 106.1, 79.1, 78.8, 78.6, 43.7, 43.5,
(m, 2H), 7.46–7.50 (m, 2H), 6.99–7.34 (m, 3H), 4.49 and 4.86 21.0, 19.9; HRMS (ESI-TOF) m/z Calcd for C19H14Cl2N2O2 [M+H]+
(2s, 2H), 3.59 and 3.96 (2t, 3JH–H=5.7 and 3JH–H=6.1 Hz, 2H), 373.0510, found 373.0507.
2.81 and 2.94 (2t, 3JH–H=5.7 and 3JH–H=5.9 Hz, 2H); 13C NMR 1-(4-Nitrophenyl)-2-(1,3,4,9-tetrahydro-2H-pyrido[3,4-
(125 MHz, CDCl3): δ=189.7, 189.6, 165.4, 165.0, 141.5, 133.8, b]indol-2-yl)ethane-1,2-dione (3ab). Red solid (261 mg, 75%);
133.4, 132.9, 132.2, 131.4, 131.3, 131.0, 130.6, 130.4, 130.3, mp 195–196 oC; 1H NMR (500 MHz, DMSO-d6): δ=10.65 and
130.0, 129.4, 128.9, 120.3, 120.1, 46.8, 43.3, 43.0, 39.2, 28.7, 11.00 (2s, 1H), 8.14–8.43 (m, 4H), 7.28–7.44 (m, 2H), 6.96–7.08
27.7; HRMS (ESI-TOF) m/z Calcd for C17H13BrClNO2 [M+H]+ (m, 2H), 4.62 and 4.92 (2s, 2H), 3.69 and 4.05 (2t, 3JH–H=4.8
377.9896, found 377.9895.
and 3JH–H=5.0 Hz, 2H), 2.70 and 2.88 (2t, 3JH–H=5.4 and 3JH–
H=5.9 Hz, 2H); 13C NMR (125 MHz, DMSO-d6): δ=189.9, 189.6,
1-Phenyl-2-(1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indol-2-
yl)ethane-1,2-dione (3x). Red solid (203 mg, 67%); mp 127– 164.8, 164.3, 150.9, 150.8, 136.8, 135.9, 131.0, 131.0, 130.7,
128 oC; 1H NMR (500 MHz, , DMSO-d6): δ=10.62 and 11.00 (2s, 129.2, 129.0, 126.2, 126.2, 124.4, 124.3, 123.6, 121.1, 121.0,
1H), 7.64–7.92 (m, 4H), 7.27–7.43 (m, 3H), 6.98–7.06 (m, 2H), 118.5, 117.6, 117.5, 111.0, 106.9, 106.0, 79.1, 79.0, 78.8, 78.6,
4.54 and 4.90 (2s, 2H), 3.63 and 4.03 (2t, 3JH–H=5.7 and 3JH– 43.7, 43.4, 21.3, 20.3; HRMS (ESI-TOF) m/z Calcd for
H=6.1 Hz, 2H), 2.67 and 2.87 (2t, 3JH–H=5.4 and 3JH–H=5.9 Hz, C19H15N3O4 [M+H]+ 350.1140, found 350.1142.
2H); 13C NMR (125 MHz, DMSO-d6): δ=191.6, 191.4, 165.8, 1-(4-Chlorophenyl)-2-(1,3,4,9-tetrahydro-2H-pyrido[3,4-
165.3, 135.9, 135.8, 135.1, 132.4, 132.3, 129.4, 129.3, 129.3, b]indol-2-yl)ethane-1,2-dione (3ac). Red solid (246 mg, 73%);
129.1, 129.0, 126.2, 121.0, 120.9, 118.6, 118.5, 117.6, 117.4, mp 108–109 oC; 1H NMR (500 MHz, DMSO-d6): δ=10.57 and
111.0, 111.0, 107.0, 106.0, 79.1, 78.8, 78.5, 43.6, 43.3, 21.2, 10.93 (2s, 1H), 7.65–7.82 (m, 4H), 7.23–7.39 (m, 2H), 6.99–
20.3; HRMS (ESI-TOF) m/z Calcd for C19H16N2O2 [M+H]+ 7.03 (m, 1H), 6.91–6.95 (m, 1H), 4.51 and 4.85 (2s, 2H), 3.59
305.1290, found 305.1289.
and 3.98 (2t, 3JH–H=4.8 and 3JH–H=5.0 Hz, 2H), 2.64 and 2.83
(2t, 3JH–H=5.4 and 3JH–H=5.9 Hz, 2H); 13C NMR (125 MHz,
1-(4-Bromophenyl)-2-(1,3,4,9-tetrahydro-2H-pyrido[3,4-
b]indol-2-yl)ethane-1,2-dione (3y). White solid (275 mg, 72%); DMSO-d6): δ=190.6, 190.4, 165.4, 165.0, 136.0, 136.0, 132.6,
mp 240–241 oC; 1H NMR (500 MHz, DMSO-d6): δ=10.61 and 131.8, 131.6, 131.5, 131.1, 131.0, 129.6, 129.4, 129.1, 126.3,
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