10.1002/adsc.201901213
Advanced Synthesis & Catalysis
132.2, 130.3, 125.5, 123.1, 120.3, 120.1, 119.6, 115.2, 127.7, 126.8, 124.2, 123.7, 122.6, 119.4, 119.2, 112.5,
112.0, 111.3, 68.1, 55.5. MS (EI, 70 eV. m/z (relative 112.0, 66.7. MS (EI, 70 eV. m/z (relative intensity)): 429
intensity)): 455 (11), 453 (54), 311 (100), 309 (51), 246 (89), 302 (100), 222 (62), 207 (22), 177 (29), 151 (39).
(30), 217 (38). HRMS: calcd for C17H13INOSe (ESI-TOF, HRMS: calcd for C14H9INSSe (ESI-TOF, M + H+)
M + H+) 453.9207, found: 424.9198.
429.8666, found: 429.8657.
3-Iodo-2-(pyridin-3-yl)-4H-selenopheno[3,2-b]indole
(2j). The product was isolated by column
chromatography (hexane and ethyl acetate 95:5 as
eluent) as a yellow solid. Yield: 0.058g (55%); mp
175.5-181.3 °C. 1H NMR (DMSO-d6 400 MHz): δ (ppm)
11.68 (s, 1H), 8.85 (s, 1H), 8.63 (s, 1H), 8.03 (d, J = 8.0
Hz, 1H), 7.81 (d, J = 7.9 Hz, 1H), 7.59 (d, J = 8.2 Hz,
1H), 7.55-7.52 (m, 1H), 7.26 (t, J = 8.0 Hz, 1H), 7.13 (t,
J = 8.0 Hz, 1H). 13C{1H}(NMR DMSO-d6 100 MHz): δ
(ppm) 149.1, 149.0, 147.0, 139.8, 139.6, 136.7, 124.2,
123.8, 123.1, 119.7, 119.6, 114.1, 112.7, 69.6. MS (EI,
70 eV. m/z (relative intensity)): 424 (32), 297 (31), 281
(30), 207 (100), 190 (15), 73 (34). HRMS: calcd for
C15H10IN2Se (ESI-TOF, M + H+) 424.9054, found:
424.9045.
2-(4-Chlorophenyl)-3-iodo-4H-selenopheno[3,2-
b]indole (2f). The product was isolated by column
chromatography (hexane and ethyl acetate 99:1 as
eluent) as a brown solid. Yield: 0.074g (65%), mp 174.4-
175.5 °C. 1H NMR (DMSO-d6 400 MHz): δ (ppm) 11.61
(s, 1H), 7.80-7.77 (m, 1H), 7.64 (d, J = 8.0 Hz, 2H),
7.59-7.55 (m, 3H), 7.25 (t, J = 8.0 Hz, 1H), 7.12 (t, J =
8.0 Hz, 1H). 13C NMR (100 MHz, DMSO): δ (ppm)
146.1, 142.3, 139.5, 135.7, 133.1, 130.8, 128.8, 124.2,
122.9, 119.5, 119.5, 113.4, 112.7, 68.5. MS (EI, 70 eV.
m/z (relative intensity)): 459 (35), 457 (85), 330 (100),
295 (61), 214 (46), 187 (25). HRMS: calcd for
C16H10IClNSe (ESI-TOF, M + H+) 457.8712, found:
457.8703.
2-Butyl-3-iodo-4H-selenopheno[3,2-b]indole (2k). The
product was isolated by column chromatography (hexane
and ethyl acetate 99:1 as eluent) as a brown oil. Yield:
0.079g (79%). 1H NMR (CDCl3 400 MHz): δ (ppm) 8.18
(s, 1H), 7.59 (d, J = 7.8 Hz, 1H), 7.42 (d, J = 8.0 Hz, 1H),
7.22 (t, J = 7.4 Hz, 1H), 7.16 (t, J = 7.4 Hz, 1H), 2.91 (t,
J = 7.5 Hz, 2H), 1.71 (quint, J = 7.5 Hz, 2H), 1.45 (sex, J
= 7.4 Hz, 2H), 0.96 (t, J = 7.3 Hz, 3H). 13C{1H}(NMR
CDCl3 100 MHz): δ (ppm) 149.1, 144.7, 138.5, 125.5,
122.7, 120.1, 119.1, 112.2, 111.1, 66.1, 35.1, 33.7, 22.2,
13.9. MS (EI, 70 eV. m/z (relative intensity)): 403 (59),
360 (100), 358 (51), 233 (34), 195 (26), 167 (36).
HRMS: calcd for C14H15INSe (ESI-TOF, M + H+)
403.9414, found: 403.9416.
3-Iodo-2-pentyl-4H-selenopheno[3,2-b]indole (2l). The
product was isolated by column chromatography (hexane
and ethyl acetate 99:1 as eluent) as a brow oil. Yield:
0.075g (73%). 1H NMR (CDCl3 400 MHz): δ (ppm) 8.22
(s, 1H), 7.61 (d, J = 8.0 Hz, 1H), 7.46 (d, J = 8.1 Hz, 1H),
7.27-7.23 (m, 1H), 7.17 (t, J = 7.6, 1H), 2.93 (t, J = 8.0
Hz, 2H), 1.74 (quint, J = 7.6 Hz, 2H), 1.46-1.35 (m, 4H),
0.92 (t, J = 7.1 Hz, 3H). 13C{1H}(NMR CDCl3 100
MHz): δ (ppm) 149.2, 144.7, 138.6, 125.6, 122.8, 120.2,
119.2, 112.2, 111.1, 66.1, 35.3, 31.1, 31.2, 22.4, 13.1.
MS (EI, 70 eV. m/z (relative intensity)): 417 (32), 359
(60), 233 (21), 207 (100), 167 (25), 154 (37). HRMS:
calcd for C15H17INSe (ESI-TOF, M + H+) 417.9571,
found: 417.9564.
2-(2-Chlorophenyl)-3-iodo-4H-selenopheno[3,2-
b]indole (2g). The product was isolated by column
chromatography (hexane and ethyl acetate 99:1 as
eluent) as a brown solid. Yield: 0.068g (60%), mp 222.8-
224.4 °C. 1H NMR (DMSO-d6 400 MHz): δ (ppm) 11.63
(s, 1H), 7.78 (d, J = 7.9 Hz, 1H), 7.63-7.57 (m, 2H),
7.53-7.44 (m, 3H), 7.26 (t, J = 8.0, 1H), 7.13 (t, J = 8.0,
1H). 13C{1H}(NMR DMSO-d6 100 MHz): δ (ppm) 145.7,
141.2, 139.4, 135.8, 133.1, 132.6, 130.6, 129.6, 127.1,
124.2, 122.8, 119.5, 119.4, 114.2, 112.6, 72.1. MS (EI,
70 eV. m/z (relative intensity)): 459 (30), 457 (86), 330
(54), 295 (85), 250 (81), 214 (100). HRMS: calcd for
C16H10IClNSe (ESI-TOF, M + H+) 457.8712, found:
457.8710.
3-Iodo-2-(naphthalen-1-yl)-4H-selenopheno[3,2-
b]indole (2h). The product was isolated by column
chromatography (hexane and ethyl acetate 99:1 as
eluent) as a brown solid. Yield: 0.104g (88%), mp 180.5-
1
183.9 °C. H NMR (CDCl3 400 MHz): δ (ppm) 8.35 (s,
1H), 7.95-7.87 (m, 3H), 7.69 (d, J = 7.8 Hz, 1H), 7.52
(m, 5H), 7.31 (t, J = 8.0 Hz, 1H), 7.22 (t, J = 8.0 Hz, 1H).
13C{1H}(NMR CDCl3 100 MHz): δ (ppm) 145.1, 143.8,
138.8, 134.4, 133.6, 131.7, 129.4, 129.1, 128.2, 126.5,
126.4, 126.2, 125.4, 125.0, 123.4, 120.4, 119.6, 115.7,
112.1, 69.3. 77Se NMR (77 MHz, in CDCl3 with
diphenyl diselenide as external reference) δ (ppm)
575.32. MS (EI, 70 eV. m/z (relative intensity)): 474 (15),
473 (73), 346 (100), 264 (61), 207 (26), 172 (49).
HRMS: calcd for C20H13INSe (ESI-TOF, M + H+)
473.9258, found: 473.9249.
2-Hexyl-3-iodo-4H-selenopheno[3,2-b]indole
(2m).
The product was isolated by column chromatography
(hexane and ethyl acetate 99:1 as eluent) as a black oil.
1
Yield: 0.083g (78%). H NMR (CDCl3 400 MHz): δ
(ppm) 8.21 (s, 1H), 7.60 (d, t, J = 8.0 Hz, 1H), 7.45 (d, J
= 8.0 Hz, 1H), 7.24 (t, J = 8.0 Hz, 1H), 7.17 t, J = 8.0 Hz,
1H), 2.93 (t, J = 8.0 Hz, 2H), 1.74 (quint, 7.9 Hz, 2H),
1.48-1.41 (m, 2H), 1.36-1.32 (m, 4H), 0.90 (t, J = 8.0 Hz,
3H). 13C{1H}(NMR CDCl3 100 MHz): δ (ppm) 149.2,
144.7, 138.5, 125.5, 122.8, 120.1, 119.1, 112.2, 111.1,
66.1, 35.4, 31.6, 28.7, 22.5, 14.0. MS (EI, 70 eV. m/z
(relative intensity)): 431 (58), 360 (100), 356 (60), 233
(33), 167 (29), 154 (35). HRMS: calcd for C16H19INSe
(ESI-TOF, M + H+) 431.9727, found: 431.9719.
3-Iodo-2-(thiophen-3-yl)-4H-selenopheno[3,2-b]indole
(2i). The product was isolated by column
chromatography (hexane and ethyl acetate 99:1 as
eluent) as a brown solid. Yield: 0.041g (39%); mp 184.8-
186.8 °C. 1H NMR (DMSO-d6 400 MHz): δ (ppm) 11.51
(s, 1H), 7.90 (dd, J = 2.9, 1.3 Hz, 1H), 7.74 (d, J = 8.0
Hz, 1H), 7.70 (dd, J =5.0, 3.9 Hz, 1H), 7.57 (d, J = 8.2
Hz, 1H), 7.50 (dd, J = 5.0, 1.3 Hz, 1H), 7.24 (t, J = 8.0
Hz, 1H), 7.11 (t, J = 8.0 Hz, 1H). 13C{1H}(NMR
DMSO-d6 100 MHz): δ (ppm) 146.9, 139.5, 138.6, 137.0,
8
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