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Organic & Biomolecular Chemistry
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ARTICLE
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on silica gel (PE/EA 8:1→5:1) afforded the title compound 3at (34.2
mg, 60% yield) as a yellow solid. mp 177 – 179 °C. 1H NMR (400 MHz,
CDCl3) δ 8.94 (brs, 1H), 8.09 (d, J = 1.0 Hz, 1H), 8.03 (d, J = 8.4 Hz, 1H),
7.97 (d, J = 8.0 Hz, 1H), 7.93 (d, J = 8.0 Hz, 1H), 7.67 – 7.59 (m, 3H),
7.09 (dd, J = 8.0, 0.6 Hz, 1H), 7.02 (td, J = 7.7, 1.2 Hz, 1H), 6.73 (td, J =
7.6, 1.2 Hz, 1H), 6.36 (dd, J = 7.8, 0.8 Hz, 1H), 5.64 (brs, 1H). 13C NMR
(101 MHz, CDCl3) δ 171.2, 161.2, 149.9, 134.4, 133.1, 132.3, 129.4,
128.7, 128.1, 128.0, 127.7, 127.4, 125.3, 124.6, 124.4, 122.8, 118.5,
DOI: 10.1039/C9OB01553A
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+
110.2, 91.0. HRMS (ESI) m/z calculated for C19H14NO2 [M+H+]
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288.1019, found 288.1027.
(Z)-3-(Amino(thiophen-2-yl)methylene)benzofuran-2(3H)-one
(3au). According to the general procedure, the reaction was carried
out using 1a (30.2 mg, 0.2 mmol) and 2u (30.4 mg, 0.2 mmol).
Purification of the crude product by flash column chromatography
on silica gel (PE/EA 8:1→5:1) afforded the title compound 3au (32.0
mg, 66% yield) as a yellow solid. mp 185 – 186 °C. 1H NMR (400 MHz,
CDCl3) δ 8.83 (brs, 1H), 7.61 (dd, J = 5.0, 1.2 Hz, 1H), 7.54 (dd, J = 3.6,
1.2 Hz, 1H), 7.23 (dd, J = 5.0, 3.6 Hz, 1H), 7.11 – 7.05 (m, 2H), 6.90 –
6.86 (m, 1H), 6.83 – 6.81 (m, 1H), 5.47 (brs, 1H). 13C NMR (101 MHz,
CDCl3) δ 171.1, 153.6, 149.9, 134.9, 130.1, 129.3, 128.2, 125.0, 124.9,
122.9, 118.7, 110.3, 92.1. HRMS (ESI) m/z calculated for C13H10NO2S+
[M+H+] 244.0427, found 244.0435.
(Z)-3-(Amino(thiophen-3-yl)methylene)benzofuran-2(3H)-one
(3av). According to the general procedure, the reaction was carried
out using 1a (30.2 mg, 0.2 mmol) and 2v (30.4 mg, 0.2 mmol).
Purification of the crude product by flash column chromatography
on silica gel (PE/EA 8:1→4:1) afforded the title compound 3av (26.9
mg, 55% yield) as a yellow solid. mp 206 – 207 °C. 1H NMR (400 MHz,
CDCl3) δ 8.84 (brs, 1H), 7.73 (dd, J = 2.9, 1.2 Hz, 1H), 7.55 (dd, J = 5.0,
3.0 Hz, 1H). 7.33 (dd, J = 5.0, 1.1 Hz, 1H), 7.11 – 7.03 (m, 2H), 6.87 (td,
J = 7.5, 1.3 Hz, 1H), 6.65 (d, J = 7.4 Hz, 1H), 5.46 (brs, 1H). 13C NMR
(101 MHz, CDCl3) δ 171.2, 155.9, 149.9, 135.7, 127.9, 127.1, 127.0,
125.2, 124.6, 122.9, 118.5, 110.3, 91.4. HRMS (ESI) m/z calculated for
C13H10NO2S+ [M+H+] 244.0427, found 244.0425.
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Conflicts of interest
There are no conflicts to declare.
Acknowledgements
The authors acknowledge the financial support from, the
Transforming Medicine Cross Research Fund of SJTU (ZH2018
QNA44), the Innovation Fund (IFPM016A002) from Joint
Research Center for Precision Medicine of Shanghai Jiao Tong
University, the Municipal Human Resources Development
Program for Outstanding Young Talents in Medical and Health
Sciences in Shanghai (2017YQ048) and the Drug Innovation
Major Project of the Ministry of Science and Technology of
China (2018ZX09711001-005-002). We are grateful to Mr. Zhao-
Yang Zhang (Shanghai Jiao Tong University) for providing the
assistance in the UV-visible spectra tests.
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Notes and references
10 | J. Name., 2012, 00, 1-3
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