Beilstein J. Org. Chem. 2019, 15, 2822–2829.
77.05; H, 6.13; N, 10.39 %; ESIMS (MeOH, m/z): 263 Skłodowska-Curie actions (MSCA), under grant agreement No
[Z-1a − H]−, 264 [Z − 1a]+, 265 [Z-1a + H]+.
749788 – PHOTORNA. I thank Prof. Dr. Heiko Ihmels
(Universität Siegen, Germany) for fruitful discussions and valu-
able advices.
(Z)-2-(4-Methoxybenzylidene)indolin-3-one (Z-1b)
Brownish-golden powder, yield 60% (172 mg, 0.68 mmol); mp
180–181 °С (lit. [20]: 180–181 °С); Rf 0.75 (hexane/EtOAc 1:1,
v/v); 1H NMR (500 MHz, DMSO-d6) δ 3.82 (s, 3H, H-17), 6.65
(s, 1H, H-10), 6.90 (t, , J = 7.8 Hz, 1H, H-5), 7.04 (d, J =
8.8 Hz, 2H, H-13, H-15), 7.14 (d, J = 8.1 Hz, 1H, H-3), 7.51
(ddd, J = 8.4, 7.1, 1.1 Hz, 1H, H-4), 7.57 (d, J = 7.6 Hz, 1H,
H-6), 7.71 (d, J = 8.8 Hz, 2H, H-12, H-16), 9.68 (s, 1H, H-1)
ppm; 13C NMR (126 MHz, DMSO-d6) δ 55.3 (1C, C-17), 110.5
(1C, C-10), 112.6 (1C, C-3), 114.6 (2C, C-13, C-15), 119.5 (1C,
C-5), 120.2 (1C, C-7), 123.9 (1C, C-6), 126.6 (1C, C-11), 131.7
(2C, C-12, C-16), 133.1 (1C, C-9), 136.0 (1C, C-4), 153.9 (1C,
C-2), 159.6 (1C, C-14), 186.0 (1C, C-8) ppm); Anal. calcd for
C16H13NO2: C, 76.48; H, 5.21; N, 5.57; found: C, 76.31 H,
5.15; N, 5.50 %; ESIMS (MeOH, m/z): 250 [Z-1b − H]−.
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References
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(Z)-2-(3,4-Dimethoxybenzylidene)indolin-3-one
(Z-1c)
Orange crystals, yield 66% (211 mg, 0.75 mmol); mp
191–192 °С; Rf 0.56 (hexane/EtOAc 1:1, v/v); 1H NMR
(500 MHz, DMSO-d6) δ 3.82 (s, 3H, H-18), 3.85 (s, 3H, H-17),
6.66 (s, 1H, H-10), 6.91 (t, J = 7.8 Hz, 1H, H-5), 7.06 (d, J =
8.4 Hz, 1H, H-15), 7.14 (d, J = 8.1 Hz, 1H, H-3), 7.29 (d, J =
2.0 Hz, 1H, H-12), 7.35 (dd, J = 8.7, 2.0 Hz, 1H, H-16), 7.51
(ddd, J = 8.3, 6.9, 1.1 Hz, 1H, H-4), 7.58 (d, J = 7.6 Hz, 1H,
H-6), 9.66 (s, 1H, H-1) ppm; 13C NMR (126 MHz, DMSO-d6)
δ 55.6 (1C, C-18), 55.7 (1C, C-17), 111.1 (1C, C-10), 112.0
(1C, C-15), 112.7 (1C, C-3), 113.8 (1C, C-12), 119.6 (1C, C-5),
120.4 (1C, C-7), 123.3 (1C, C-16), 123.9 (1C, C-6), 126.8 (1C,
C-11), 133.3 (1C, C-9), 136.0 (1C, C-4), 148.9 (1C, C-14),
149.5 (1C, C-13), 154.0 (1C, C-2), 186.0 (1C, C-8) ppm; Anal.
calcd for C17H15NO3: C, 72.58; H, 5.37; N, 4.98; found C,
72.80; H, 5.27; N, 4.89 %; ESIMS (MeOH, m/z): 280
[Z-1c − H]−.
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Supporting Information
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Supporting Information File 1
Additional spectral data, detailed description of the
experiments performed, NMR of compounds Z-1a–c and
LED characteristics.
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Acknowledgements
This project has received funding from the European Union’s
Horizon 2020 research and innovation programme, Marie
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