Organic & Biomolecular Chemistry
Paper
4e: Yellow solid (73.3 mg, 56% yield), mp 156–158 °C; IR
Notes and references
(KBr, cm−1) 3311, 2961, 1722, 1702, 1649, 1580, 1503, 1411,
1
1338, 1314, 1165, 1122, 862, 764, 698 cm−1; H NMR (CDCl3,
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500 MHz): δ 9.45 (s, 1H), 7.59 (d, J = 8.1 Hz, 1H), 7.43 (d, J =
7.3 Hz, 1H), 7.05 (t, J = 7.4 Hz, 1H), 6.97 (s, 2H), 3.93 (s, 3H),
3.88 (s, 6H), 3.58 (s, 2H); 13C NMR (CDCl3, 125 MHz) δ 195.7,
176.5, 153.0, 145.5, 141.8, 133.0, 130.7, 128.9, 127.1, 120.9,
118.0, 107.1, 61.0, 56.3, 35.2. HRMS (ESI) m/z calcd for
C18H18NO5+ [M + H]+ 328.1179, found 328.1183.
5c: Yellow solid (76.4 mg, 76% yield), mp 156–158 °C;
IR (KBr) 3358, 1628, 1586, 1586, 1513, 1406, 1265, 1035, 872,
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P. Bondiskey, G. B. McGaughey, M. G. Bock,
G. D. Hartman, C. Tang, J. Ballard, Y. Kuo,
T. Prueksaritanont, C. E. Nuss, S. M. Doran, S. V. Fox,
1
856 cm−1. H NMR (CDCl3, 500 MHz) δ 10.36 (s, 1H), 7.91 (d,
J = 7.8 Hz, 1H), 7.82 (d, J = 8.7 Hz, 2H), 7.63 (d, J = 7.5 Hz, 1H),
7.37 (s, 1H), 7.17 (t, J = 7.7 Hz, 1H), 7.01 (d, J = 8.7 Hz, 2H),
6.65 (s, 1H), 3.90 (s, 3H); 13C NMR (CDCl3, 125 MHz) δ 196.8,
162.6, 135.8, 131.9, 131.6, 129.4, 127.6, 126.7, 125.7, 119.8,
+
118.6, 113.6, 102.5, 55.5. HRMS (ESI) m/z calcd for C16H14NO2
[M + H]+ 252.1019, found 252.1026.
5d: Yellow solid (91.1 mg, 81% yield), mp 98–100 °C;
IR (KBr) 3351, 2914, 1626, 1596, 1580, 1510, 1404, 1265, 1139,
1023, 888, 867, 734, 627 cm−1 1H NMR (CDCl3, 500 MHz):
;
δ 10.32 (s, 1H), 7.91 (d, J = 7.8 Hz, 1H), 7.65 (d, J = 7.5 Hz, 1H),
7.44–7.42 (m, 2H), 7.37 (s, 1H), 7.16 (t, J = 7.7 Hz, 1H),
6.95–6.92 (m, 1H), 6.65 (s, 1H), 3.97 (s, 3H), 3.95 (s, 3H); 13C
NMR (CDCl3, 125 MHz) δ 196.7, 152.3, 148.9, 135.8, 131.6,
129.5, 127.5, 126.7, 125.7, 124.3, 119.2, 118.4, 112.2, 109.9,
+
102.6, 56.1, 56.1. HRMS (ESI) m/z calcd for C17H16NO3 [M +
H]+ 282.1125, found 282.1132.
5f: Yellow solid (102.3 mg, 86% yield), mp 155–157 °C; IR
(KBr) 3361, 1636, 1581, 1576, 1532, 1404, 1143, 1013, 877, 721,
1
636 cm−1; H NMR (CDCl3, 500 MHz): δ 10.48 (s, 1H), 7.96 (d,
J = 7.8 Hz, 1H), 7.88 (d, J = 8.4 Hz, 2H), 7.75 (d, J = 8.3 Hz, 2H),
7.70–7.68 (m, 3H), 7.51 (t, J = 7.6 Hz, 2H), 7.44–7.40 (m, 2H),
7.19 (t, J = 7.7 Hz, 1H), 6.69 (s, 1H); 13C NMR (CDCl3,
125 MHz) δ 197.8, 144.4, 140.2, 137.8, 135.7, 130.1, 129.5,
129.0, 128.1, 127.2, 126.5, 125.9, 119.7, 119.5, 118.7, 103.7,
102.7. HRMS (ESI) m/z calcd for C21H16NO+ [M + H]+ 298.1226,
found 298.1231.
5g: Yellow solid (98.7 mg, 91% yield), mp 87–89 °C; IR (KBr)
3345, 1631, 1592, 1570, 1512, 1408, 1255, 1141, 1033, 871, 743,
1
631 cm−1; H NMR (CDCl3, 500 MHz): δ 10.48 (s, 1H), 8.27 (s,
1H), 8.00–7.93 (m, 4H), 7.90–7.87 (m, 2H), 7.69 (d, J = 8.2 Hz,
1H), 7.43 (s, 1H), 7.32 (s, 1H), 7.15–7.20 (m, 2H); 13C NMR
(CDCl3, 125 MHz) δ 198.1, 136.3, 134.8, 132.3, 130.5, 129.5,
129.2, 128.2, 127.9, 127.2, 126.8, 126.5, 126.1, 125.9, 125.8,
119.7, 118.7. HRMS (ESI) m/z calcd for C19H14NO+ [M + H]+
272.1070, found 272.1076.
Acknowledgements
Financial support was provided by the National Natural
Science Foundation of China (no. 21102105) and Zhejiang
Provincial Natural Science Foundation (no. LY14B020009).
This journal is © The Royal Society of Chemistry 2014
Org. Biomol. Chem.