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doi.org/10.1002/ejoc.202001413
EurJOC
European Journal of Organic Chemistry
8.0 Hz, 1H), 7.70–7.63 (m, 2H), 7.52–7.46 (m, 1H), 7.40 (s, 1H), 6.68
13b-Methyl-6,7-dihydro-5H-benzo[1,2]indolizino[7,8-b]indol-
9(13bH)-one (5am): Pale yellow solid (43.6 mg, yield 76 %), m.p.
(s, 1H), 4.72–4.60 (m, 1H), 4.34 (dd, J = 13.3, 6.0 Hz, 1H), 3.67 (s, 3H),
3.39–3.36 (m, 1H), 2.81–2.64 (m, 2H), 1.79 (s, 3H), 1.26 (d, J = 6.1 Hz, 223–224 °C. 1H NMR (600 MHz, CDCl3) δ 8.36 (s, 1H), 8.11 (d, J =
3H), 1.20 (d, J = 6.1 Hz, 3H); 13C NMR (150 MHz, DMSO-d6) δ =
166.55, 151.22, 149.01, 145.13, 132.11, 130.86, 130.35, 128.30,
125.73, 123.28, 122.82, 114.34, 112.62, 70.51, 63.31, 55.45, 34.66,
7.8 Hz, 1H), 7.99 (d, J = 7.9 Hz, 1H), 7.85 (d, J = 7.5 Hz, 1H), 7.61–
7.55 (m, 1H), 7.45–7.37 (m, 1H), 7.32 (d, J = 8.0 Hz, 1H), 7.24–7.19
(m, 1H), 7.19–7.13 (m, 1H), 4.76 (dd, J = 13.2, 6.1 Hz, 1H), 3.43–3.25
28.79, 28.11, 22.09, 21.53; LRMS (ESI) m/z: 338 [M + H]+; HRMS (ESI) (m, 1H), 3.15–2.94 (m, 1H), 2.71 (dd, J = 15.8, 4.1 Hz, 1H), 1.94 (s,
m/z calculated for C21H23NO3 + H+ 338.1751, found 338.1751.
3H); 13C NMR (150 MHz, CDCl3) δ = 168.75, 151.40, 136.16, 132.11,
131.93, 130.84, 128.20, 124.84, 123.99, 122.83, 121.77, 120.03,
119.24, 113.15, 111.46, 64.24, 35.13, 26.29, 24.14; LRMS (ESI) m/z:
289 [M + H]+; HRMS (ESI) m/z calculated for C19H16N2O + H+
289.1335, found 289.1330.
11b-Methyl-4,5-dihydrothieno[3′,2′:3,4]pyrido[2,1-a]isoindol-
7(11bH)-one (5ah): Yellow solid (36.2 mg, yield 71 %), m.p. 199–
200 °C. 1H NMR (600 MHz, CDCl3) δ 7.85 (dd, J = 7.6, 0.9 Hz, 1H),
7.76–7.73 (m, 1H), 7.62–7.56 (m, 1H), 7.48–7.42 (m, 1H), 7.20 (d, J =
5.3 Hz, 1H), 7.15 (dd, J = 5.3, 0.8 Hz, 1H), 4.74 (ddd, J = 13.4, 6.4,
0.9 Hz, 1H), 3.36 (ddd, J = 13.4, 11.7, 4.6 Hz, 1H), 3.06–2.93 (m, 1H),
2.87 (dd, J = 16.1, 4.4 Hz, 1H), 1.76 (s, 3H); 13C NMR (150 MHz, CDCl3)
δ = 167.96, 150.16, 137.65, 133.51, 132.17, 131.00, 128.45, 124.25,
124.11, 123.81, 122.02, 63.86, 35.22, 27.78, 25.49; LRMS (ESI) m/z:
256 [M + H]+; HRMS (ESI) m/z calculated for C15H13NOS + H+
256.0791, found 256.0785.
13b-Methyl-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino-
[8,7-b]indol-5-one (5an): White solid (37.7 mg, yield 65 %), m.p.
283–284 °C. 1H NMR (500 MHz, CDCl3) δ 8.83 (s, 1H), 7.94 (d, J =
7.7 Hz, 1H), 7.89 (d, J = 7.5 Hz, 1H), 7.63–7.55 (m, 1H), 7.49–7.42 (m,
2H), 7.36 (d, J = 8.1 Hz, 1H), 7.20–7.13 (m, 1H), 7.11–7.06 (m, 1H),
4.83 (dd, J = 13.5, 5.7 Hz, 1H), 3.45 (ddd, J = 13.4, 11.6, 4.9 Hz, 1H),
2.99 (ddd, J = 15.5, 11.5, 6.3 Hz, 1H), 2.87 (dd, J = 15.5, 4.4 Hz, 1H),
1.92 (s, 3H); 13C NMR (125 MHz, CDCl3) δ = 168.41, 148.97, 136.53,
134.89, 132.28, 131.24, 128.88, 126.78, 124.51, 122.63, 121.54,
120.07, 118.87, 111.25, 108.30, 7 62.40, 35.85, 26.42, 21.95; LRMS
(ESI) m/z: 289 [M + H]+; HRMS (ESI) m/z calculated for C19H16N2O +
H+ 289.1335, found 289.1330.
11b-Methyl-4,5-dihydrothieno[2′,3′:3,4]pyrido[2,1-a]isoindol-
7(11bH)-one (5ai): Pale yellow solid (40.9 mg, yield 80 %), m.p.
155–156 °C. 1H NMR (500 MHz, CDCl3) δ 7.83 (d, J = 7.6 Hz, 1H),
7.75 (d, J = 7.6 Hz, 1H), 7.64–7.57 (m, 1H), 7.50 –7.41 (m, 1H), 7.16
(d, J = 5.0 Hz, 1H), 6.73 (d, J = 5.0 Hz, 1H), 4.68 (dd, J = 13.5, 6.3 Hz,
1H), 3.39–3.28 (m, 1H), 2.90–2.79 (m, 1H), 2.77–2.65 (m, 1H), 1.84 (s,
3H); 13C NMR (100 MHz, CDCl3) δ = 167.81, 150.33, 138.44, 133.50,
132.22, 130.88, 128.58, 127.08, 124.01, 123.69, 122.01, 63.71, 34.95,
29.56, 26.24; LRMS (ESI) m/z: 256 [M + H]+; HRMS (ESI) m/z calcu-
lated for C15H13NOS + H+ 256.0791, found 256.0796.
12b-Benzyl-5,6-dihydro-[1,3]dioxolo[4,5-g]isoindolo[1,2-a]iso-
quinolin-8(12bH)-one (5ao): Colorless oil (51.6 mg, yield 70 %). 1H
NMR (600 MHz, DMSO-d6) δ 8.44 (d, J = 7.8 Hz, 1H), 7.80 (s, 1H),
7.69–7.58 (m, 1H), 7.39 (d, J = 7.1 Hz, 1H), 7.37–7.33 (m, 1H), 7.05–
6.92 (m, 3H), 6.81 (dd, J = 6.3, 3.0 Hz, 2H), 6.72 (s, 1H), 6.04 (s, 1H),
5.95 (s, 1H), 4.39–4.25 (m, 1H), 3.70 (d, J = 13.9 Hz, 1H), 3.54–3.43
(m, 2H), 2.82–2.66 (m, 2H); 13C NMR (150 MHz, CDCl3) δ = 168.10,
148.31, 146.86, 146.63, 134.85, 131.92, 131.60, 131.26, 129.93,
128.41, 127.87, 127.58, 126.91, 123.75, 122.85, 109.31, 106.34,
101.32, 67.35, 46.91, 35.56, 29.92; LRMS (ESI) m/z: 370 [M + H]+;
HRMS (ESI) m/z calculated for C24H19NO3 + H+ 370.1438, found
370.1436.
12b-Methyl-5,6-dihydropyrrolo[2′,1′:3,4]pyrazino[2,1-a]iso-
indol-8(12bH)-one (5aj): Pale yellow solid (41.8 mg, yield 88 %),
m.p. 156–157 °C. 1H NMR (500 MHz, CDCl3) δ 7.83 (d, J = 7.6 Hz,
1H), 7.76 (d, J = 7.6 Hz, 1H), 7.65–7.55 (m, 1H), 7.51–7.38 (m, 1H),
6.53 (dd, J = 2.4, 1.8 Hz, 1H), 6.25 (dd, J = 3.6, 1.5 Hz, 1H), 6.20–6.11
(m, 1H), 4.72–4.68 (m, 1H), 4.03–3.91 (m, 2H), 3.61–3.55 (m, 1H), 1.80
(s, 3H); 13C NMR (100 MHz, CDCl3) δ = 168.12, 150.96, 132.61, 130.66,
130.39, 128.44, 123.99, 122.08, 119.61, 108.61, 104.22, 61.87, 44.46,
35.33, 28.99; LRMS (ESI) m/z: 239 [M + H]+; HRMS (ESI) m/z calcu-
lated for C15H14N2O + H+ 239.1179, found 239.1177.
12b-Benzyl-2-ethoxy-3-methoxy-5,6-dihydroisoindolo[1,2-a]-
isoquinolin-8(12bH)-one (5ap): White solid (54.2 mg, yield 68 %),
m.p. 170–171 °C. 1H NMR (600 MHz, DMSO-d6) δ 8.44 (d, J = 7.7 Hz,
1H), 7.68–7.62 (m, 1H), 7.61 (s, 1H), 7.39 (d, J = 7.1 Hz, 1H), 7.37–
7.32 (m, 1H), 7.02–6.97 (m, 3H), 6.83 (dd, J = 6.5, 2.9 Hz, 2H), 6.72
(s, 1H), 4.42–4.32 (m, 1H), 4.28–4.19 (m, 1H), 4.13–4.06 (m, 1H), 3.77
(d, J = 13.8 Hz, 1H), 3.71 (s, 3H), 3.47–3.41 (m, 2H), 2.81–2.69 (m,
2H), 1.37 (t, J = 6.9 Hz, 3H); 13C NMR (150 MHz, CDCl3) δ = 168.10,
148.82, 148.59, 146.92, 134.99, 132.02, 131.53, 130.03, 129.94,
128.34, 127.87, 126.90, 126.72, 123.84, 122.73, 112.27, 111.66, 67.04,
65.11, 55.99, 47.00, 35.65, 29.44, 15.00; LRMS (ESI) m/z: 400 [M +
H]+; HRMS (ESI) m/z calculated for C26H25NO3 + H+ 400.1907, found
400.1908.
11b-Methyl-4,5-dihydro-3H-pyrrolo[3′,2′:3,4]pyrido[2,1-a]iso-
indol-7(11bH)-one (5ak): Pale yellow solid (35.4 mg, yield 74 %),
m.p. 236–237 °C. 1H NMR (500 MHz, CDCl3) δ 7.97 (s, 1H), 7.81 (d,
J = 7.6 Hz, 1H), 7.72 (d, J = 7.6 Hz, 1H), 7.60–7.52 (m, 1H), 7.45–7.37
(m, 1H), 6.70–6.61 (m, 1H), 6.34–6.26 (m, 1H), 4.70 (dd, J = 13.4,
6.3 Hz, 1H), 3.36 (ddd, J = 13.3, 11.7, 4.8 Hz, 1H), 2.87 (ddd, J = 15.4,
11.6, 6.4 Hz, 1H), 2.62 (dd, J = 15.3, 4.7 Hz, 1H), 1.73 (s, 3H); 13C
NMR (150 MHz, CDCl3) δ = 168.29, 151.84, 132.06, 130.68, 128.03,
123.89, 123.63, 121.68, 120.84, 117.42, 104.56, 62.83, 34.85, 28.03,
23.20; LRMS (ESI) m/z: 239 [M + H]+; HRMS (ESI) m/z calculated for
C15H14N2O + H+ 239.1179, found 239.1177.
12b-Benzyl-10-methyl-5,6-dihydro-[1,3]dioxolo[4,5-g]isoind-
olo[1,2-a]isoquinolin-8(12bH)-one (5aq): White solid (50.1 mg,
yield 65 %), m.p. 220–221 °C. 1H NMR (600 MHz, CDCl3) δ 7.77 (d,
J = 7.9 Hz, 1H), 7.44 (s, 1H), 7.39 (d, J = 7.6 Hz, 1H), 7.30 (s,1H), 7.10–
6.99 (m, 3H), 6.79–6.73 (m, 2H), 6.57 (s, 1H), 5.98 (d, J = 1.3 Hz, 1H),
5.90 (d, J = 1.3 Hz, 1H), 4.55 (ddd, J = 13.0, 6.4, 1.3 Hz, 1H), 3.47 (d,
J = 14.1 Hz, 1H), 3.38 (d, J = 14.1 Hz, 1H), 3.29–3.21 (m, 1H), 3.00–
2.89 (m, 1H), 2.68 (dd, J = 16.1, 3.2 Hz, 1H), 2.36 (s, 3H). 13C NMR
13b-Methyl-6,7-dihydroisoindolo[1′,2′:3,4]pyrazino[1,2-a]indol-
9(13bH)-one (5al): Pale yellow solid (35.9 mg, yield 62 %), m.p.
1
235–236 °C. H NMR (500 MHz, CDCl3) δ 7.87 (dd, J = 13.5, 7.6 Hz,
2H), 7.70–7.64 (m, 1H), 7.57 (d, J = 7.8 Hz, 1H), 7.52–7.46 (m, 1H),
7.28–7.25 (m, 1H), 7.22–7.16 (m, 1H), 7.15–7.08 (m, 1H), 6.64 (s, 1H),
4.87 (dd, J = 13.8, 4.9 Hz, 1H), 4.27 (dd, J = 11.6, 4.6 Hz, 1H), 4.03–
3.93 (m, 1H), 3.70 (ddd, J = 13.6, 12.1, 4.8 Hz, 1H), 1.92 (s, 3H); 13C
NMR (125 MHz, CDCl3) δ = 167.79, 150.22, 137.85, 135.83, 132.73, (150 MHz, CDCl3) δ = 168.34, 146.82, 146.61, 145.69, 138.51, 135.06,
130.54, 128.77, 127.85, 124.13, 122.23, 121.95, 120.64, 120.55, 132.60, 132.06, 131.61, 129.98, 127.90, 127.50, 126.89, 124.03,
109.36, 98.06, 61.82, 41.47, 34.76, 28.85; LRMS (ESI) m/z: 289 [M + 122.58, 109.28, 106.40, 101.29, 67.20, 46.93, 35.63, 29.89, 21.29.
H]+; HRMS (ESI) m/z calculated for C19H16N2O + H+ 289.1335, found LRMS (ESI) m/z: 384 [M + H]+; HRMS (ESI) m/z calculated for
289.1332.
C25H21NO3 + H+ 384.1594, found 384.1586.
7354 © 2020 Wiley-VCH GmbH
Eur. J. Org. Chem. 2020, 7343–7357