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Organic & Biomolecular Chemistry
Page 8 of 11
ARTICLE
Journal Name
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oxylate (6jc): Yield 90% (85.7 mg), light yellow solid. H NMR (400 : Yield 31% (16.7 mg), light yellow oil. 1H NMR (400 MHz, CDCl3) δ =
MHz, CDCl3) δ = 8.26 (s, 1H), 7.29 (d, J = 8.7 Hz, 2H), 7.01 (d, J = 8.7 8.21 (d, J = 7.7 Hz, 1H), 7.51–7.44 (m, 2H), D7O.4I4: –107..130439(/mD,0O4HB0),1470.239F
Hz, 2H), 6.76 (s, 1H), 4.75 (t, J = 6.9 Hz, 2H), 4.42 (q, J = 7.0 Hz, 2H), (s, 2H), 6.56 (s, 1H), 4.13 (t, J = 6.6 Hz, 2H), 3.05 (t, J = 6.6 Hz, 2H);
4.10–3.88 (m, 6H), 3.84 (s, 3H), 3.13 (t, J = 6.8 Hz, 2H), 1.46 (t, J = 13C NMR (101 MHz, CDCl3) δ = 135.93, 134.79, 132.04, 131.02,
7.1 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ = 164.13, 162.30, 159.96, 129.22, 128.97, 128.43, 128.41, 128.17, 128.10, 127.56, 124.38,
159.41, 150.88, 148.84, 134.26, 128.92, 125.78, 125.47, 125.41, 118.15, 112.62, 88.64, 42.50, 29.54. HRMS (ESI): m/z [M+H]+ calcd
118.51, 118.43, 115.07, 114.73, 110.73, 110.48, 61.77, 56.43, 56.25, for C19H15N2: 271.1230, found 271.1233.
55.72, 43.69, 28.14, 14.38. HRMS (ESI): m/z [M+H]+ calcd for 2-(4-methoxyphenyl)-3-phenyl-5,6-dihydropyrrolo[2,1-a]isoquinol-
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C26H25N2O7: 477.1656, found 477.1664.
Ethyl 2,3-dimethoxy-9,14-dioxo-5,6,9,14-tetrahydrobenzo[5,6]iso-
ine (6kf): Yield 20% (14.0 mg), light yellow oil. H NMR (400 MHz,
CDCl3) δ = 7.48–7.43 (m, 5H), 7.41–7.30 (m, 3H), 7.24–7.19 (m, 1H),
indolo[1,2-a]isoquinoline-8-carboxylate (6jd): Yield 78% (67.3 mg), 7.07 (dd, J = 16.7, 8.1 Hz, 2H), 6.94 (d, J = 8.6 Hz, 2H), 6.36 (s, 1H),
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light yellow solid. H NMR (400 MHz, CDCl3) δ = 8.95 (s, 1H), 8.39– 4.14 (t, J = 6.3 Hz, 2H), 3.87 (s, 3H), 3.05 (t, J = 6.2 Hz, 2H); 13C NMR
8.28 (m, 1H), 8.24–8.11 (m, 1H), 7.81–7.63 (m, 2H), 6.77 (s, 1H), (101 MHz, CDCl3) δ = 158.49, 133.61, 132.77, 132.57, 130.40,
4.55 (q, J = 7.1 Hz, 2H), 4.29 (t, J = 6.7 Hz, 2H), 4.12 (s, 3H), 3.96 (s, 130.28, 130.02, 129.23, 128.95, 128.68, 127.88, 127.19, 126.78,
3H), 3.07 (t, J = 6.6 Hz, 2H), 1.51 (t, J = 7.1 Hz, 3H); 13C NMR (101 125.68, 124.57, 122.70, 114.15, 111.27, 55.50, 42.68, 30.63. HRMS
MHz, CDCl3) δ = 179.94, 179.79, 161.84, 150.50, 148.00, 136.53, (ESI): m/z [M+H]+ calcd for C25H22NO: 352.1696, found 352.1698.
136.13, 134.96, 133.42, 133.05, 127.54, 127.20, 126.77, 126.20, 5,8-dimethyl-2-phenyl-3a,4,5,9b-tetrahydro-1H-pyrrolo[3,4-c]qui-
123.28, 119.41, 116.64, 112.67, 110.50, 62.69, 56.55, 56.22, 43.54, noline-1,3(2H)-dione (8a): Yield 62% (38.0 mg), light yellow solid. 1H
28.85, 14.24. The data was consistent with the known literature.6f
NMR (400 MHz, CDCl3) δ = 7.36 (t, J = 7.5 Hz, 2H), 7.31–7.25 (m, 2H),
7.24–7.17 (m, 2H), 6.96 (dd, J = 15.6, 8.7 Hz, 1H), 6.59 (d, J = 8.3 Hz,
8,10-diphenyl-5H-pyrrolo[3',4':3,4]pyrrolo[2,1-a]isoquinoline-9,11
(6H, 10H)-dione (6ka): Yield 56% (43.7 mg), light yellow solid. 1H 1H), 4.05 (d, J = 9.6 Hz, 1H), 3.52 (dd, J = 11.4, 2.6 Hz, 1H), 3.48–3.42
NMR (400 MHz, CDCl3) δ = 8.59 (d, J = 7.3 Hz, 1H), 7.69 (d, J = 6.8 Hz, (m, 1H), 2.99 (dd, J = 11.4, 4.3 Hz, 1H), 2.73 (s, 3H), 2.23 (s, 3H); 13
C
2H), 7.59–7.25 (m, 11H), 4.31 (s, 2H), 3.16 (s, 2H); 13C NMR (101 NMR (101 MHz, CDCl3) δ = 177.95, 176.04, 146.43, 132.24, 131.04,
MHz, CDCl3) δ = 163.91, 163.74, 133.29, 132.98, 132.09, 130.59, 129.47, 129.36, 129.19, 128.70, 126.59, 118.76, 112.86, 51.15,
129.75, 129.59, 129.46, 129.06, 128.95, 128.38, 128.31, 127.79, 43.71, 42.37, 39.84, 20.65. The data was consistent with the known
127.63, 127.56, 127.20, 126.97, 118.26, 115.77, 43.38, 29.26. HRMS literature.11b
(ESI): m/z [M+H]+ calcd for C26H19N2O2: 391.1441, found 391.1440.
2-(4-chlorophenyl)-5,8-dimethyl-3a,4,5,9b-tetrahydro-1H-pyrrolo-
10-(4-chlorophenyl)-8-phenyl-5H-pyrrolo[3',4':3,4]pyrrolo[2,1-a]is- [3,4-c]quinoline-1,3(2H)-dione (8b): Yield 57% (38.8 mg), light
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oquinoline-9,11(6H,10H)-dione (6kb): Yield 33% (28.0 mg), light yellow solid. H NMR (400 MHz, CDCl3) δ 7.39–7.30 (m, 2H), 7.23–
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yellow solid. H NMR (400 MHz, CDCl3) δ = 8.56 (d, J = 7.6 Hz, 1H), 7.10 (m, 3H), 7.03–6.94 (m, 1H), 6.61 (d, J = 8.3 Hz, 1H), 4.06 (d, J =
7.67 (d, J = 7.2 Hz, 2H), 7.61–7.48 (m, 3H), 7.48–7.27 (m, 7H), 4.31 9.6 Hz, 1H), 3.52 (dd, J = 11.4, 2.6 Hz, 1H), 3.49-3.42 (m, 1H), 3.00
(t, J = 6.7 Hz, 3H), 3.16 (t, J = 6.4 Hz, 3H); 13C NMR (101 MHz, CDCl3) (dd, J = 11.4, 4.3 Hz, 1H), 2.74 (s, 3H), 2.24 (s, 3H); 13C NMR (101
δ = 163.59, 163.43, 133.20, 133.10, 132.11, 131.81, 130.80, 129.95, MHz, CDCl3) δ 177.68, 175.77, 146.36, 134.46, 131.01, 130.69,
129.71, 129.59, 129.11, 129.10, 128.33, 128.28, 128.25, 127.84, 130.37, 129.58, 129.38, 127.80, 118.61, 112.98, 51.11, 43.70, 42.35,
127.58, 126.83, 117.98, 115.47, 43.37, 29.21. HRMS (ESI): m/z 39.87, 20.66. The data was consistent with the known literature.11b
[M+H]+ calcd for C26H18ClN2O2: 425.1051, found 425.1054.
3-(4-methoxyphenyl)-5,8-dimethyl-3a,4,5,9b-tetrahydro-1H-pyrro-
10-(4-methoxyphenyl)-8-phenyl-5H-pyrrolo[3',4':3,4]pyrrolo[2,1-a] lo[3,4-c]quinoline-1,3(2H)-dione (8c): Yield 68% (45.7 mg), light
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isoquinoline-9,11(6H,10H)-dione (6kc): Yield 52% (43.7 mg), light yellow solid. H NMR (400 MHz, CDCl3) δ = 7.36 (s, 1H), 7.22–7.13
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yellow solid. H NMR (400 MHz, CDCl3) δ = 8.57 (d, J = 7.6 Hz, 1H), (m, 2H), 7.05 (dd, J = 8.2, 1.6 Hz, 1H), 6.99–6.86 (m, 2H), 6.67 (d, J =
7.68 (d, J = 7.3 Hz, 2H), 7.60–7.27 (m, 8H), 6.99 (d, J = 8.4 Hz, 2H), 8.3 Hz, 1H), 4.12 (d, J = 9.5 Hz, 1H), 3.81 (s, 3H), 3.59 (dd, J = 11.4,
4.30 (t, J = 6.1 Hz, 2H), 3.85 (s, 3H), 3.15 (t, J = 5.9 Hz, 2H); 13C NMR 2.7 Hz, 1H), 3.55–3.47 (m, 1H), 3.07 (dd, J = 11.4, 4.4 Hz, 1H), 2.81
(101 MHz, CDCl3) δ 164.20, 164.04, 158.94, 132.86, 132.06, 130.46, (s, 3H), 2.31 (s, 3H); 13C NMR (101 MHz, CDCl3) δ = 178.18, 176.25,
129.72, 129.54, 129.40, 129.04, 128.50, 128.39, 128.29, 127.78, 159.63, 146.38, 131.06, 129.44, 129.39, 127.81, 124.91, 118.87,
127.59, 126.98, 126.02, 118.26, 115.78, 114.35, 55.70, 43.33, 29.25. 114.52, 112.88, 55.69, 51.17, 43.61, 42.30, 39.88, 20.67. The data
HRMS (ESI): m/z [M+H]+ calcd for C27H21N2O3: 421.1547, found was consistent with the known literature.11b
421.1544.
Ethyl 2-(1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)acetate (9): Yield
21% (19.5 mg), light yellow solid. 1H NMR (400 MHz, CDCl3) δ = 8.09
8-phenyl-5,6-dihydrobenzo[5,6]isoindolo[1,2-a]isoquinoline-9,14-
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dione (6kd): Yield 57% (42.8 mg), light yellow solid. H NMR (400 (d, J = 7.7 Hz, 1H), 7.44 (t, J = 7.5, 1.2 Hz, 1H), 7.35 (t, J = 7.5 Hz, 1H),
MHz, CDCl3) δ = 9.11 (d, J = 7.6 Hz, 1H), 8.33 (d, J = 7.0 Hz, 1H), 7.20 (d, J = 7.5 Hz, 1H), 4.35 (s, 2H), 4.23 (q, J = 7.1 Hz, 2H), 3.67 (t, J
8.15 (d, J = 7.0 Hz, 1H), 7.88–7.43 (m, 8H), 7.36 (t, J = 7.1 Hz, 1H), = 6.6 Hz, 2H), 3.08 (t, J = 6.6 Hz, 2H), 1.29 (t, J = 7.1 Hz, 3H); 13C NMR
7.25 (d, J = 6.4 Hz, 1H), 3.959 (t, J = 5.4 Hz, 2H), 3.00 (s, 2H); 13
C
(101 MHz, CDCl3) δ = 169.51, 165.21, 138.64, 132.15, 129.05,
NMR (101 MHz, CDCl3) δ = 180.38, 180.34, 138.08, 136.45, 135.51, 128.68, 127.26, 127.20, 61.49, 49.40, 47.62, 28.27, 14.40. HRMS
134.53, 134.00, 133.14, 132.95, 130.68, 129.71, 128.81, 128.64, (ESI): m/z [M+H]+ calcd for C13H15NO3: 233.1052, found 233.1055.
127.65, 127.57, 127.46, 127.33, 126.59, 119.73, 117.68, 42.51, The data was consistent with the known literature.14
29.76. HRMS (ESI): m/z [M+H]+ calcd for C26H18NO2: 376.1332, found
376.1336.
Conflicts of interest
3-phenyl-5,6-dihydropyrrolo[2,1-a]isoquinoline-1-carbonitrile (6ke)
8 | J. Name., 2012, 00, 1-3
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