G
C. Raji Reddy et al.
Paper
Synthesis
1H NMR (500 MHz, CDCl3): = 8.37 (s, 1 H), 8.14 (d, J = 16.4 Hz, 1 H),
8.06 (d, J = 8.5 Hz, 1 H), 7.81 (d, J = 8.2 Hz, 1 H), 7.76–7.71 (m, 1 H),
7.55 (dd, J = 8.0, 7.1 Hz, 1 H), 6.87 (d, J = 16.4 Hz, 1 H), 2.58 (t, J = 7.1
Hz, 2 H), 2.46 (s, 3 H), 1.77 (dd, J = 14.5, 7.3 Hz, 2 H), 1.14 (t, J = 7.4 Hz,
3 H).
13C NMR (100 MHz, CDCl3): = 198.0, 148.5, 143.8, 139.8, 133.4,
131.1, 129.9, 129.3, 128.9, 128.1, 127.6, 126.7, 97.0, 79.1, 27.2, 21.9,
21.7, 13.8.
8-(2-Oxopropyl)-13-pentylisoindolo[2′,1′:3,4]pyrimido[1,6-a]-
indol-6(8H)-one (5c)
Yellow solid; yield: 119 mg (78%); mp 178–180 °C.
IR (KBr): 3710, 3523, 3425, 3141, 2925, 1691, 1377, 760 cm–1
.
1H NMR (500 MHz, CDCl3): = 8.69–8.64 (m, 1 H), 7.78 (d, J = 7.8 Hz, 1
H), 7.70–7.64 (m, 1 H), 7.53 (d, J = 7.6 Hz, 1 H), 7.47 (t, J = 7.4 Hz, 1 H),
7.41 (t, J = 7.2 Hz, 1 H), 7.38–7.32 (m, 2 H), 6.68 (s, 1 H), 5.98 (dd, J =
8.3, 3.0 Hz, 1 H), 3.86 (dd, J = 17.7, 3.1 Hz, 1 H), 3.04–2.97 (m, 2 H),
2.91 (dd, J = 17.7, 8.4 Hz, 1 H), 2.22 (s, 3 H), 1.81–1.74 (m, 2 H), 1.59–
1.50 (m, 2 H), 1.47–1.40 (m, 2 H), 0.95 (t, J = 7.3 Hz, 3 H).
HRMS-ESI: m/z calcd for C18H18NO [M + H]+: 264.1388; found:
264.1382.
13C NMR (100 MHz, CDCl3): = 205.9, 147.1, 142.6, 138.4, 134.2,
133.3, 132.7, 130.8, 129.9, 129.0, 123.8, 123.8, 123.5, 122.7, 119.7,
116.1, 108.4, 97.4, 58.9, 47.3, 32.3, 30.7, 28.7, 27.0, 22.8, 14.3.
HRMS (ESI): m/z calcd for C26H27N2O2 [M + H]+: 399.2073; found:
399.2057.
(E)-1-Ethynyl-2-[2-(methylsulfinyl)vinyl]benzene (4m)
To a stirred solution of (E)-trimethyl({2-[2-(methylsulfinyl)vinyl]phe-
nyl}ethynyl)silane (800 mg, 3.00 mmol) was added K2CO3 (1.20 g, 9.1
mmol) in MeOH at 0 °C and the mixture was stirred for 30 min to
complete the reaction at rt. The obtained crude product was purified
by column chromatography over silica gel (7% EtOAc in PE) to afford
4m as a pale yellow oil; yield: 464 mg (80%).
13-(Hydroxymethyl)-8-(2-oxopropyl)isoindolo[2′,1′:3,4]-
pyrimido[1,6-a]indol-6(8H)-one (5d)
IR (KBr): 3292, 2923, 1733, 1592, 1446, 1242, 944, 761, 654 cm–1
.
Yellow solid; yield: 113 mg (82%); mp 181–183 °C.
1H NMR (400 MHz, CDCl3): = 7.48–7.42 (m, 2 H), 7.28 (td, J = 7.4, 3.9
Hz, 1 H), 7.13 (td, J = 7.5, 1.2 Hz, 1 H), 6.94 (d, J = 15.5 Hz, 1 H), 6.79 (d,
J = 15.5 Hz, 1 H), 3.32 (s, 1 H), 2.41 (s, 3 H).
13C NMR (100 MHz, CDCl3): = 139.11, 133.35, 129.13, 128.47,
126.30, 124.10, 122.15, 119.43, 82.30, 81.80, 14.80.
IR (KBr): 3513, 3023, 1694, 1387, 758 cm–1
.
1H NMR (400 MHz, CDCl3): = 8.52 (d, J = 7.0 Hz, 1 H), 8.02 (d, J = 7.9
Hz, 1 H), 7.54 (d, J = 7.4 Hz, 1 H), 7.47 (t, J = 6.6 Hz, 1 H), 7.42–7.35 (m,
2 H), 7.26 (d, J = 23.1 Hz, 3 H), 6.71 (s, 1 H), 5.77 (d, J = 7.9 Hz, 1 H),
5.12–4.99 (m, 2 H), 3.75 (d, J = 17.6 Hz, 1 H), 2.85 (dd, J = 17.7, 8.3 Hz,
1 H), 2.18 (s, 3 H), 1.71 (s, 1 H).
13C NMR (100 MHz, CDCl3): = 205.7, 146.8, 142.6, 137.5, 137.1,
133.0, 131.5, 130.6, 130.2, 129.2, 124.6, 123.9, 123.4, 122.8, 119.7,
115.8, 105.7, 97.2, 59.1, 57.3, 46.8, 30.7.
HRMS-ESI: m/z calcd for C11H11OS [M + H]+: 191.0531; found:
191.0525.
8-(2-Oxopropyl)-13-propylisoindolo[2′,1′:3,4]pyrimido[1,6-a]-
indol-6(8H)-one (5a)
HRMS (ESI): m/z calcd for C22H19N2O3 [M + H]+: 359.1394; found:
359.1396.
Yellow solid; yield: 115 mg (81%); mp 180–182 °C.
IR (KBr): 3515, 3379, 2963, 1682, 1381, 1170, 762 cm–1
.
1H NMR (300 MHz, CDCl3 + DMSO-d6): = 8.54 (d, J = 7.7 Hz, 1 H), 7.85
(d, J = 7.8 Hz, 1 H), 7.67 (d, J = 7.1 Hz, 1 H), 7.56–7.42 (m, 3 H), 7.36–
7.23 (m, 2 H), 6.80 (s, 1 H), 5.82 (dd, J = 6.9, 3.0 Hz, 1 H), 3.65 (dd, J =
17.5, 3.2 Hz, 1 H), 3.13 (dd, J = 17.5, 7.3 Hz, 1 H), 3.05–2.94 (m, 2 H),
2.13 (s, 3 H), 1.84–1.67 (m, 2 H), 1.11 (t, J = 7.3 Hz, 3 H).
13C NMR (75 MHz, CDCl3 + DMSO-d6): = 205.5, 145.9, 142.1, 138.0,
134.4, 132.4, 131.8, 130.2, 129.3, 128.7, 123.3, 123.2, 123.1, 121.9,
119.5, 115.2, 106.8, 96.8, 58.5, 45.8, 30.3, 27.8, 21.7, 13.8.
13-Cyclopropyl-8-(2-oxopropyl)isoindolo[2′,1′:3,4]pyrimido-
[1,6-a]indol-6(8H)-one (5e)
Yellow solid; yield: 105 mg (74%); mp 180–182 °C.
IR (KBr): 3893, 3015, 1694, 1467, 1379, 760 cm–1
.
1H NMR (500 MHz, CDCl3): = 8.65 (d, J = 7.8 Hz, 1 H), 8.29 (d, J = 7.8
Hz, 1 H), 7.67 (dd, J = 6.8, 1.4 Hz, 1 H), 7.52 (d, J = 7.6 Hz, 1 H), 7.47 (t,
J = 7.3 Hz, 1 H), 7.44–7.39 (m, J = 7.4, 0.9 Hz, 1 H), 7.37–7.30 (m, 2 H),
6.90 (s, 1 H), 5.96 (dd, J = 8.4, 2.9 Hz, 1 H), 3.85 (dd, J = 17.7, 3.1 Hz, 1
H), 2.90 (dd, J = 17.7, 8.4 Hz, 1 H), 2.21 (s, 3 H), 2.07–1.95 (m, 1 H),
1.32–1.19 (m, 2 H), 0.92–0.78 (m, 2 H).
HRMS-ESI: m/z calcd for C24H23N2O2 [M + H]+: 371.1760; found:
371.1760.
13C NMR (100 MHz, CDCl3): = 205.8, 147.0, 142.7, 138.5, 137.6,
133.1, 132.4, 130.8, 129.7, 128.6, 125.2, 123.8, 123.5, 122.6, 119.7,
116.0, 107.7, 98.8, 59.1, 47.2, 30.7, 9.1, 8.0.
HRMS-ESI: m/z calcd for C24H21N2O2 [M]+: 369.1603; found:
369.1603.
13-Butyl-8-(2-oxopropyl)isoindolo[2′,1′:3,4]pyrimido[1,6-a]indol-
6(8H)-one (5b)
Yellow solid; yield: 117 mg (79%); mp 190–192 °C.
IR (KBr): 3563, 3334, 2955, 1693, 1382, 761 cm–1
.
1H NMR (400 MHz, CDCl3): = 8.70–8.63 (m, 1 H), 7.79 (d, J = 7.8 Hz, 1
H), 7.70–7.64 (m, 1 H), 7.53 (d, J = 7.6 Hz, 1 H), 7.47 (t, J = 7.3 Hz, 1 H),
7.44–7.37 (m, 1 H), 7.37–7.30 (m, 2 H), 6.68 (s, 1 H), 5.98 (dd, J = 8.2,
2.5 Hz, 1 H), 3.86 (dd, J = 17.7, 3.1 Hz, 1 H), 3.09–2.97 (m, 2 H), 2.91
(dd, J = 17.7, 8.4 Hz, 1 H), 2.22 (s, 3 H), 1.83–1.71 (m, J = 12.2, 7.6 Hz, 2
H), 1.63–1.52 (m, 2 H), 1.03 (t, J = 7.3 Hz, 3 H).
13C NMR (100 MHz, CDCl3): = 205.8, 146.9, 142.5, 138.4, 134.2,
133.3, 132.6, 130.7, 129.4, 128.9, 123.8 (2 C), 123.4, 122.6, 119.6,
116.1, 108.3, 97.4, 58.9, 47.2, 31.1, 30.7, 26.7, 23.2, 14.2.
8-(2-Oxopropyl)isoindolo[2′,1′:3,4]pyrimido[1,6-a]indol-6(8H)-
one (5f)
Yellow solid; yield: 98 mg (78%); mp 175–177 °C.
IR (KBr): 3830, 3520, 3025, 1693, 1380, 759 cm–1
.
1H NMR (400 MHz, CDCl3): = 8.68–8.60 (m, 1 H), 7.69–7.60 (m, 2 H),
7.50 (d, J = 6.9 Hz, 1 H), 7.47–7.38 (m, 2 H), 7.37–7.29 (m, 2 H), 6.81 (s,
1 H), 6.58 (s, 1 H), 5.96 (dd, J = 8.5, 2.7 Hz, 1 H), 3.90 (dd, J = 17.8, 3.1
Hz, 1 H), 2.91 (dd, J = 17.8, 8.6 Hz, 1 H), 2.22 (s, 3 H).
HRMS (ESI): m/z calcd for C25H25N2O2 [M + H]+: 385.1916; found:
385.1917.
© 2020. Thieme. All rights reserved. Synthesis 2020, 52, A–J