Molecules 2019, 24, 3649
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31.0, 36.8, 39.6, 40.5, 108.5, 121.4, 121.9, 130.0, 132.8, 133.1, 144.1, 168.0. HRMS (ESI) [M + Na]+ calcd for
C26H28N4O6S2Na 551.1035, found, 551.1060.
(E)-1,1’-bis((1-(m-tolylsulfonyl)aziridin-2-yl)methyl)[3,3’-biindolinylidene]-2,2’-dione (7e). Red powder,
Yield 57%, m.p. 138 ◦C. IR (KBr) (
ν
max/cm−1): 1682, 1606, 1466, 1354, 1155, 1091, 740, 687.
λ
max/nm
1
(ꢀ
, M−1 cm−1) 223 (1740), 272 (868). H NMR (400.1 MHz, CDCl3):
δ
2.08 (s, 6H), 2.28 (d, J = 4.2 Hz,
2H), 2.77–2.81 (m, 2H), 3.03–3.05 (m, 2H), 3.44–3.55 (m, 2H), 4.03–4.41 (m, 2H), 6.62 (d, J = 7.8 Hz, 2H),
6.92–7.16 (m, 6H), 7.19 (d, J = 6.2 Hz, 2H), 7.16–7.20 (m, 2H), 7.40–7.44 (m, 2H), 8.90 (d, J = 7.9 Hz,
2H). 13C NMR (100.6 MHz, CDCl3):
δ 20.1, 30.2, 36.6, 39.7, 39.9, 107.2, 107.3, 120.2, 121.4, 123.7, 127.0,
127.6, 128.7, 128.8, 131.4, 131.6, 133.5, 135.9, 138.2, 142.7, 166.5. HRMS (ESI) [M + Na]+ calcd for
C36H32N4O6S2Na 703.1661, found, 703.1674.
(E)-1,◦1’-bis((1-tosylaziridin-2-yl)methyl)[3,3’-biindolinylidene]-2,2’-dione (7f). Red powder, Yield 53%,
m.p. 144 C. IR (KBr) (ν λmax/nm (ꢀ,
max/cm−1): 1688, 1603, 1466, 1321, 1259, 1175, 1088, 1014, 793.
M−1 cm−1) 212 (1438), 272 (966). 1H NMR (400.1 MHz, CDCl3):
δ 2.10 (b, 6H), 2.28 (s, 2H), 2.79 (t,
J = 6.2 Hz, 2H), 3.00 (s, 2H), 3.35–3.47 (m, 2H), 4.08 (td, J = 14.3, 2.6 Hz, 2H), 6.60–6.61 (m, 2H), 6.85 (t,
J = 7.7 Hz, 4H), 6.95 (t, J = 7.6 Hz, 2H), 7.19 (b, 2H), 7.47 (t, J = 7.16 Hz, 4H), 8.92 (d, J = 7.8 Hz, 2H).
13C NMR (100.6 MHz, CDCl3):
δ 20.4, 30.1, 30.2, 36.7, 36.8, 39.9, 40.0, 107.3, 107.4, 120.2, 121.3, 126.5,
128.2, 128.36, 128.39, 131.56, 131.59, 133.0, 133.1, 142.7, 143.7, 166.5 HRMS (ESI) [M + Na]+ calcd for
C36H32N4O6S2Na 703.1661, found, 703.1655.
(E)-1,1’-bis((1-(phenylsulfonyl)aziridin-2-yl)methyl)[3,3’-biindolinylidene]-2,2’-dione (7g). Red powder,
◦
Yield 54%, m.p. 148 C. IR (KBr) (
ν
max/cm−1): 1679, 1612, 1435, 1353, 1318, 1084, 745.
λ
max/nm (
ꢀ,
1
M−1 cm−1) 218 (1251), 245 (1857). H NMR (400.1 MHz, CDCl3):
δ 2.36–2.37 (m, 2H), 2.84–2.87 (m,
2H), 3.10–3.12 (m, 2H), 3.51–3.60 (m, 2H), 4.08–4.15 (m, 2H), 6.67 (d, J = 7.8, 2H), 7.01 (t, J = 7.7 Hz,
2H), 7.16–7.21 (m, 6H), 7.23–7.35 (m, 2H), 7.68 (d, J = 8.0 Hz, 2H), 8.93 (d, J = 7.9 Hz, 2H). 13C NMR
(100.6 MHz, CDCl3):
δ 31.40, 31.43, 37.66, 37.69, 40.7, 40.8, 108.30, 108.34, 121.3, 122.4, 127.5, 128.75,
128.77, 129.64, 129.69, 132.5, 132.7, 133.7, 137.0, 137.1, 143.7, 169.5. HRMS (ESI) [M + Na]+ calcd for
C36H32N4O6S2Na 675.1345, found, 675.1371.
(E)-1,1’-bis((1-((4-isopropylphenyl)sulfonyl)aziridin-2-yl)methyl)-3,3’-biindolinylidene]-2,2’-dione (7h).
Red powder, Yield 56%, m.p. 136 ◦C. IR (KBr) (
ν
max/cm−1): 1691, 1603, 1321, 1158, 1092, 744.
λ
max/nm
1
(ꢀ
, M−1 cm−1) 211 (634), 272 (604). H NMR (400.1 MHz, CDCl3):
δ
1.15 (b, 12H), 2.32 (s, 2H), 2.78 (d,
J = 6.7 Hz, 2H), 3.12 (s, 2H), 3.47–3.48 (m, 2H), 3.63–3.68 (m, 2H), 4.09–4.12 (m, 2H), 6.72 (d, J = 7.5 Hz,
2H), 7.02 (t, J = 7.3 Hz, 2H), 7.13 (s, 4H), 7.26 (s, 2H), 7.66 (d, J = 7.2 Hz, 4H), 8.99 (d, J = 7.4 Hz, 2H).
13C NMR (100.6 MHz, CDCl3):
δ 22.3, 22.4, 30.3, 32.9, 36.4, 39.7, 107.4, 120.2, 121.5, 125.9, 126.8, 128.5,
131.5, 131.7, 133.5, 142.9, 154.1, 166.7. HRMS (ESI) [M + H]+ calcd for C40H41N4O6S2 737.2468, found,
737.2501.
(E)-1,1’-bis((1-((((1S,4S/R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methyl)sulfon◦yl)aziridin-2-
yl)methyl)[3,3’-biindolinylidene]-2,2’-dione (7i). Red powder, Yield 52%, m.p. 186 C. IR (KBr)
(ν
max/cm−1): 1740, 1693, 1607, 1349, 1146, 1097, 665.
1H NMR (400.1 MHz, CDCl3):
λ
max/nm (
ꢀ
, M−1 cm−1) 201 (2550), 272 (1110).
δ
0.69 (s, 6H), 0.92 (s, 6H), 1.29–1.34 (m, 2H), 1.84–1.99 (m, 8H), 2.25
(b, 5H), 2.60–2.62 (m, 2H), 2.80–2.87 (m, 2H), 3.02–3.09 (m, 2H), 3.38–3.53 (m, 3H), 3.80–4.11 (m, 4H),
6.89 (d, J = 7.2 Hz, 2H), 6.98 (d, J = 7.2 Hz, 2H), 7.30 (d, J = 7.6 Hz, 2H), 9.02–9.05 (m, 2H). 13C NMR
(100.6 MHz, CDCl3):
δ 14.2, 18.5, 18.61, 18.69, 18.7, 23.7, 25.8, 30.3, 30.5, 35.5, 35.9, 39.30, 39.36, 39.42,
39.46, 41.3, 41.4, 41.5, 46.9, 47.0, 48.0, 48.2, 57.1, 64.8, 107.4, 107.5, 120.5, 121.6, 121.7, 129.0, 129.1, 131.5,
131.6, 131.7, 132.1, 143.13, 143.17, 143.2, 166.90, 166.94, 212.6, 213.1. HRMS (ESI) [M
C42H47N4O8S2 799.2835, found, 799.2875.
−
H]+ calcd for
4.2.2. General procedure for the synthesis of 6
To a magnetically stirred solution of N-allylarylsulfonamide or N-allylalkylsulfonamide (20
mmol) in dry dichloromethane (25 mL) at 0 ◦C was added dropwise a solution bromine (25 mmol) in
dichloromethane (3 mL). The reaction mixture stirred for 30 min at 0 ◦C and the solvent was removed
in vacuo. The mixture was dissolved in ethanol (15 mL) and added to aqueous NaOH solution (1