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cmꢁ1): 3412, 2923, 1736, 1624, 1608, 1585, 1466, 1337, 1226,
1182, 826, 516. HRMS (ESIꢁ): calcd for C13H7Br2O3 [M ꢁ H]ꢁ
368.8762; found 368.8767.
3.6.24a White solid (33 mg, 50%); mp 210–212 ꢀC, Rf (3%
EtOAc/hexane) 0.5. 1H NMR (400 MHz, CDCl3) d 8.29 (d, J ¼ 2.6
Hz, 2H, Ar–H), 7.69 (dd, J ¼ 8.8, 2.7 Hz, 2H, Ar–H), 7.47 (d, J ¼
9.0 Hz, 2H, Ar–H) ppm. 13C NMR (100 MHz, CDCl3) d 175.24,
154.56, 135.45, 130.32, 126.28, 122.50, 119.96 ppm. IR (KBr,
cmꢁ1): 3084, 1669, 1610, 1462, 1289, 825, 816. HRMS (EI+): calcd
for C13H6Cl2O2 [M]+ 263.9745; found 263.9742.
2.10.23c White solid (22 mg, 30%); mp 146–148 ꢀC, Rf (3%
1
EtOAc/hexane) 0.36. H NMR (400 MHz, CDCl3) d 10.29 (s, 2H,
–OH), 7.56 (d, J ¼ 2.6 Hz, 2H, Ar–H), 7.50 (dd, J ¼ 8.9, 2.6 Hz, 2H,
Ar–H), 7.07 (d, J ¼ 8.9 Hz, 2H, Ar–H) ppm. 13C NMR (100 MHz,
CDCl3) d 200.27, 160.31, 136.38, 131.59, 124.32, 120.56, 120.32
ppm. IR (KBr, cmꢁ1): 3263, 2926, 1625, 1611, 1585, 1465, 1339,
1224, 1185, 960, 830, 718. HRMS (ESIꢁ): calcd for C13H7Cl2O3 [M
ꢁ H]ꢁ 280.9772; found 280.9776.
3.7.24b White solid (38 mg, 54%); mp 202–204 ꢀC, Rf (20%
EtOAc/hexane) 0.2. 1H NMR (400 MHz, CDCl3) d 8.91 (d, J ¼ 2.2
Hz, 2H, Ar–H), 8.41 (dd, J ¼ 8.8, 2.3 Hz, 2H, Ar–H), 7.62 (d, J ¼
8.8 Hz, 2H, Ar–H), 2.74 (s, 6H, –COCH3) ppm. 13C NMR (100
MHz, CDCl3) d 196.38, 176.42, 158.78, 134.58, 133.68, 128.41,
121.30, 119.14, 26.85 ppm. IR (KBr, cmꢁ1): 2925, 2854, 1679,
1664, 1602, 1480, 1361, 1256, 1245, 1120, 830, 587. HRMS (EI+):
calcd for C17H12O4 [M]+ 280.0736; found 280.0733.
2.11. White solid (32 mg, 43%); mp 178–180 ꢀC, Rf (20%
1
EtOAc/hexane) 0.18. H NMR (400 MHz, CDCl3) d 10.94 (s, 2H,
–OH), 8.30 (t, J ¼ 2.4 Hz, 2H, Ar–H), 8.17 (dt, J ¼ 8.8, 2.2 Hz, 2H,
Ar–H), 7.19–7.16 (m, 2H, Ar–H), 2.56 (s, 6H, –COCH3) ppm. 13
C
3.8. White solid (34 mg, 54%); mp 228–230 ꢀC, Rf (20%
NMR (100 MHz, CDCl3) d 201.63, 195.58, 165.59, 136.22, 134.08,
129.03, 119.28, 118.94, 26.40 ppm. IR (KBr, cmꢁ1): 3141, 2925,
1678, 1627, 1588, 1482, 1360, 1272, 1214, 836. HRMS (ESI+):
calcd for C17H18NO5 [M + NH4]+ 316.1185; found 316.1184.
3.1.23d White solid (23 mg, 47%); mp 162–164 ꢀC, Rf (3%
EtOAc/hexane) 0.5. 1H NMR (400 MHz, CDCl3) d 8.35 (dd, J ¼ 8.4,
1.3 Hz, 2H, –OH), 7.75–7.71 (m, 2H, Ar–H), 7.51–7.48 (m, 2H, Ar–
H), 7.41–7.36 (m, 2H, Ar–H) ppm. 13C NMR (100 MHz, CDCl3)
d 177.42, 156.34, 134.98, 126.89, 124.07, 122.00, 118.13 ppm. IR
(KBr, cmꢁ1): 2922, 1656, 1608, 1481, 1459, 1346, 1332, 752. HRMS
(ESI+): calcd for C13H9O2 [M + H]+ 197.0603; found 197.0604.
3.2.24a White solid (22 mg, 39%); mp 128–130 ꢀC, Rf (3%
EtOAc/hexane) 0.18. 1H NMR (400 MHz, CDCl3) d 8.11 (d, J ¼ 1.9
Hz, 2H, Ar–H), 7.51 (dd, J ¼ 8.3, 2.1 Hz, 2H, Ar–H), 7.37 (d, J ¼
8.5 Hz, 2H, Ar–H), 2.46 (s, 6H, –Me) ppm. 13C NMR (100 MHz,
CDCl3) d 177.56, 154.60, 136.09, 133.63, 126.18, 121.60, 117.87,
20.99 ppm. IR (KBr, cmꢁ1): 3466, 3057, 1660, 1619, 1481, 1308,
1218, 1142, 824, 809, 794, 539. HRMS (EI+): calcd for C15H12O2
[M]+ 224.0837; found 224.0835.
1
EtOAc/hexane) 0.3. H NMR (400 MHz, CDCl3) d 10.15 (s, 2H,
–CHO), 8.86 (d, J ¼ 1.9 Hz, 2H, Ar–H), 8.34 (dd, J ¼ 8.7, 2.0 Hz,
2H, Ar–H), 7.69 (d, J ¼ 8.7 Hz, 2H, Ar–H) ppm. 13C NMR (125
MHz, CDCl3) d 190.16, 175.79, 159.48, 133.90, 133.22, 131.64,
122.02, 119.83 ppm. IR (KBr, cmꢁ1): 3438, 3075, 2851, 1699,
1673, 1608, 1478, 1452, 1239, 1168, 1115, 832. HRMS (EI+): calcd
for C15H8O4 [M]+ 252.0423; found 252.0425.
3.9.25a Yellow solid (41 mg, 57%); mp 230–232 ꢀC, Rf (20%
1
EtOAc/hexane) 0.3. H NMR (400 MHz, CDCl3) d 9.11–9.07 (m,
2H, Ar–H), 8.56–8.52 (m, 2H, Ar–H), 7.68–7.64 (m, 2H, Ar–H)
ppm. 13C NMR (100 MHz, CDCl3) d 174.29, 158.60, 144.48,
129.94, 123.31, 121.18, 120.06 ppm. IR (KBr, cmꢁ1): 2917, 1669,
1610, 1533, 1464, 1345, 1284, 1083, 834, 747, 665. HRMS (EI+):
calcd for C13H6N2O6 [M]+ 286.0226; found 286.0220.
3.10.24b White solid (28 mg, 49%); mp 316–318 C, Rf (30%
ꢀ
1
EtOAc/hexane) 0.25. H NMR (400 MHz, DMSO-d6) d 11.28 (s,
2H, –OH), 7.18 (d, J ¼ 9.2 Hz, 2H, Ar–H), 6.33–6.30 (m, 4H, Ar–H)
ppm. 13C NMR (125 MHz, DMSO-d6) d 199.34, 162.87, 160.72,
133.58, 115.30, 107.41, 102.48 ppm. IR (KBr, cmꢁ1): 3401, 2255,
2128, 1651, 1049, 1026, 1004, 826, 764, 631. HRMS (ESIꢁ): calcd
for C13H7O4 [M ꢁ H]ꢁ 227.0344; found 227.0341.
3.3. White solid (33 mg, 35%); mp 152–154 ꢀC, Rf (40%
EtOAc/hexane) 0.32. 1H NMR (400 MHz, CDCl3) d 7.49 (s, 2H, Ar–
H), 4.12 (s, 6H, –OMe), 4.07 (s, 6H, –OMe), 3.98 (s, 6H, –OMe)
ppm. 13C NMR (125 MHz, CDCl3) d 175.68, 150.27, 148.20,
146.06, 141.82, 116.99, 100.94, 62.02, 61.66, 56.47 ppm. IR (KBr,
cmꢁ1): 2940, 2852, 1649, 1597, 1470, 1424, 1383, 1208, 1127,
1104, 1058, 860, 766. HRMS (EI+): calcd for C19H20O8 [M]+
376.1158; found 376.1151.
4.25b White solid (33 mg, 27%); mp 74–76 C, Rf (3% EtOAc/
ꢀ
1
hexane) 0.3. H NMR (400 MHz, CDCl3) d 11.63 (s, 1H, –OH),
10.29 (s, 1H, –OH), 7.60–7.55 (m, 2H, Ar–H), 7.50–7.46 (m, 1H,
Ar–H), 7.07 (dd, J ¼ 8.4, 1.1 Hz, 1H, Ar–H), 6.95–6.91 (m, 1H, Ar–
H), 6.54 (d, J ¼ 2.5 Hz, 1H, Ar–H), 6.48 (dd, J ¼ 9.0, 2.5 Hz, 1H,
Ar–H), 3.88 (s, 3H, –OMe) ppm. 13C NMR (100 MHz, CDCl3)
d 200.63, 166.35, 165.80, 160.98, 135.25, 135.18, 132.56, 120.45,
118.93, 118.56, 113.36, 107.68, 101.61, 55.83 ppm. IR (KBr,
cmꢁ1): 2936, 1615, 1585, 1482, 1347, 1269, 1237, 1151, 924, 759.
HRMS (ESI+): calcd for C14H13O4 [M + H]+ 245.0814; found
245.0811.
3.4.24a White solid (26 mg, 45%); mp 158–160 ꢀC, Rf (5%
1
EtOAc/hexane) 0.3. H NMR (400 MHz, CDCl3) d 7.95 (dd, J ¼
8.3, 2.9 Hz, 2H, Ar–H), 7.54–7.45 (m, 4H, Ar–H) ppm. 13C NMR
(125 MHz, CDCl3) d 176.04, 158.97 (d, JC–F ¼ 244.4 Hz), 152.51,
123.46 (d, JC–F ¼ 25.5 Hz), 122.01 (d, JC–F ¼ 7.1 Hz), 120.21 (d, JC–
¼ 8.0 Hz), 111.52 (d, JC–F ¼ 23.4 Hz) ppm. IR (KBr, cmꢁ1): 3055,
F
1671, 1626, 1475, 1291, 1166, 1134, 819, 776, 544. HRMS (EI+):
calcd for C13H6F2O2 [M]+ 232.0336; found 232.0330.
3.5.24a White solid (41 mg, 46%); mp 192–194 ꢀC, Rf (5%
Acknowledgements
1
EtOAc/hexane) 0.2. H NMR (400 MHz, CDCl3) d 8.43–8.42 (m,
2H, Ar–H), 7.81 (ddd, J ¼ 8.9, 2.5, 0.6 Hz, 2H, Ar–H), 7.39 (dd, J ¼ The authors thank the Science and Engineering Research Board
8.9, 0.4 Hz, 2H, Ar–H) ppm. 13C NMR (100 MHz, CDCl3) (SERB) under Department of Science and Technology (DST),
d 174.94, 154.97, 138.21, 129.48, 122.95, 120.21, 117.65 ppm. IR New Delhi for funding this work (SR/S1/OC-20/2012). B. S. R.
(KBr, cmꢁ1): 1661, 1608, 1458, 1289, 1127, 813. HRMS (EI+): acknowledges the Council of Scientic and Industrial Research
calcd for C13H6Br2O2 [M]+ 351.8735; found 351.8735.
(CSIR), New Delhi for research fellowship.
75510 | RSC Adv., 2016, 6, 75505–75511
This journal is © The Royal Society of Chemistry 2016