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RSC Advances
Page 6 of 9
DOI: 10.1039/C5RA13932E
ARTICLE
Journal Name
148.7, 154.4, 161.4, 161.6; HRMS: m/z calculated for C17H12ClNO3 154.4, 160.3, 161.4; HRMS: m/z calculated for C16H17NO3 [M+Na]+:
[M+H]+: 314.0584, Found 314.0915.
294.1106, Found 294.2049.
N
-(2-Chlorobenzyl)-2-oxo-2
H
-chromene-3-carboxamide (3j). Yield-
N-Cyclohexyl-6-methyl-2-oxo-2H-chromene-3-carboxamide (3p).
79%, colorless crystalline solid, M.P. 196-198 °C; IR (KBr pellet): Yield- 60 %, colorless crystalline solid, M.P. 182-184 °C; 1H NMR
3055, 1712, 1664, 1525, 1454, 1255, 1035, 917, 802, 761, 632 cm-1; (300 MHz, CDCl3): δ 1.23-1.48 (m, 6H, -CH2-CH2-CH2-), 1.73-1.77 (m,
1H NMR (300 MHz, CDCl3): δ 4.75 (d, J= 5.8 Hz, 2H, -NH-CH2-), 7.22- 6H, -CH2-CH2-CH2-), 1.96-1.99 (m, 2H, -NH-CH-CH2-), 2.43 (s, 3H,
7.26 (m, 2H, ArH), 7.36-7.46 (m, 4H, ArH), 7.65-7.70 (2H, m, ArH), CH3), 3.96-3.99 (m, 2H,-NH-CH-CH2-), 7.26 (d, J= 4.5 Hz, 1H, H-8),
8.93 (s, 1H, H-4), 9.29 (br. s, 1H, NH); 13C NMR (100 MHz, CDCl3): δ 7.44 (d, J= 6.3 Hz, 2H, H-5, H-7), 8.40 (br. s, 1H, NH), 8.84 (s, 1H, H-
41.8, 116.7, 118.4, 118.6, 125.3, 127.0, 128.9, 129.6, 129.8, 133.7, 4); 13C NMR (75 MHz, CDCl3): δ 20.7, 24.7, 25.6, 32.8, 48.5, 116.3,
134.1, 135.3, 148.6, 154.5, 161.4, 161.7; HRMS: m/z calculated for 118.5, 118.6, 129.3, 135.0, 135.1, 148.1, 152.6, 160.5, 161.7;
C17H12ClNO3 [M+H]+: 314.0584, Found 314.0536.
HRMS: m/z calculated for C17H19NO3 [M+Na]+: 308.1263, Found
308.2237.
N
-(2-Chlorobenzyl)-8-methoxy-2-oxo-2H-chromene-3-
carboxamide (3k). Yield- 72%, colorless crystalline solid, M.P. 218-
N
-(1,3-Dihydroxy-2-(hydroxymethyl)propan-2-yl)-2-oxo-2H-
220 °C; 1H NMR (500 MHz, CDCl3): δ 4.00 (s, 3H, OCH3), 4.77 (d, chromene-3-carboxamide (3q). Yield- 70%, colorless crystalline
J=6.0 Hz, 2H, -NH-CH2-), 7.20-7.39 ( m, 5H, ArH), 7.40 (d, J= 6.5 Hz, solid, M.P. 194-196 °C; IR (KBr pellet): 2969, 1720, 1525, 1444,
1H, ArH), 7.45 (d, J= 6.5 Hz, 1H, ArH), 8.91( s, 1H, H-4), 9.31 (s, 1H, 1239, 1046, 956, 803, 745 cm-1; 1H NMR (500 MHz, DMSO-d6): δ3.66
NH); 13C NMR (125 MHz, CDCl3): δ41.9, 56.5, 115.8, 118.7, 119.4, (d, J=5.0 Hz, 6H, 3 × CH2), 4.81 (t, J=5.0 Hz, 3H, 3 × OH), 7.43(t, J= 7.5
121.1, 125.3, 127.1, 129.0, 129.7, 129.9, 133.8, 135.5, 144.3, 147.2, Hz, 1H, H-6), 7.50 (d, J= 8.5 Hz, 1H, H-8), 7.73 (t, J=8.0 Hz, 1H, H-7),
148.9, 161.0, 161.8; HRMS: m/z calculated for C18H14ClNO4 [M+H]+: 7.97 (d, J= 7.5 Hz, 1H, H-5), 8.89 and 8.96 (each s, 1H, NH and H-4);
344.0690, Found 344.0656.
13C NMR (75 MHz, DMSO-d6): δ 60.6, 62.9, 116.6, 118.9, 119.4,
125.6, 130.8, 134.6, 148.1, 154.4, 161.2, 161.4; HRMS: m/z
calculated for C14H15NO6 [M+H]+: 294.0978, Found 294.0884.
N
-((Furan-2-yl)methyl)-2-oxo-2
H
-chromene-3-carboxamide
(3l).
Yield- 89%, colorless crystalline solid, M.P. 180-182 °C; 1H NMR (300
MHz, CDCl3): δ4.66 (d, J= 6.0 Hz, 2H, -NH-CH2-), 6.32 (d, J= 6.0 Hz,
N,N-Dimethyl-2-oxo-2H-chromene-3-carboxamide (5a). Yield-
2H, furyl H-3,H-4), 7.28-7.42 (m, 3H, ArH), 7.61-7.71 (m, 2H, ArH), 74%,colorless crystalline solid, M.P. 150-152 °C; IR (KBr pellet):
8.93 (s, 1H, H-4), 9.12 (br. s, 1H, NH); 13C NMR (75 MHz, CDCl3): δ 3064, 2978, 2928, 2914, 1766, 1607, 1563, 1450, 1206, 1032, 1023,
36.8, 107.5, 110.4, 116.6, 118.3, 118.6, 125.3, 129.8, 134.1, 142.3, 775 cm-1; 1H NMR (300 MHz, CDCl3): δ 3.01 (s, 3H, CH3), 3.12 (s, 3H,
148.6, 151.0, 154.5, 161.3, 161.4; HRMS: m/z calculated for CH3), 7.29-7.37 (m, 2H, H-6, H-8), 7.52-7.61 (m, 2H, H-5, H-7), 7.91
C15H11NO4 [M+Na]+: 292.0586, Found 292.0483.
(s, 1H, H-4); 13C NMR (75 MHz, CDCl3): δ 35.3, 38.4, 116.8, 118.3,
124.9, 125.8, 128.5, 132.7, 142.9, 154.1, 157.8, 165.0; HRMS: m/z
calculated for C12H11NO3 [M+H]+: 218.0817, Found 218.1080.
N
-Isopropyl-2-oxo-2
colorless crystalline solid, M.P. 113-117 °C; 1H NMR (300 MHz,
CDCl3): δ 1.28 (d, J=6.6 Hz, 6H, 2 × CH3), 4.23-4.30 (m, 1H, CH), 7.35- 8-Methoxy-N,N-dimethyl-2-oxo-2H-chromene-3-carboxamide (5b).
H-chromene-3-carboxamide (3m). Yield- 79%,
7.42 (m, 2H, ArH), 7.63-7.70 (m, 2H, ArH), 8.68 (br. s, 1H, NH), 8.91 Yield- 70%, colorless crystalline solid, M.P. 162-164 °C; IR (KBr
(s, 1H, H-4); 13C NMR (75 MHz, CDCl3): δ 22.6, 41.9, 116.6, 118.7, pellet): 3410, 2942, 1710, 1638, 1612, 1579, 1478, 1282, 1260,
125.2, 129.7, 133.9, 148.1, 154.4, 160.5, 161.4; HRMS: m/z 1198, 1109, 771, 734, cm-1; 1H NMR (300 MHz, CDCl3): δ 3.02 (s, 3H,
calculated for C13H13NO3 [M+Na]+: 254.0793, Found 254.1358.
CH3), 3.13 (s, 3H, CH3), 3.99 (s, 3H, OCH3), 7.11-7.16 (m, 2H, H-5, H-
7), 7.27 (t, J= 8.0 Hz, 1H, H-6), 7.92(s, 1H, H-4); 13C NMR (75 MHz,
CDCl3): δ35.3, 38.3, 56.3, 114.5, 119.0, 119.8, 124.7, 126.0, 143.2,
143.8, 147.2, 157.3, 165.0; HRMS: m/z calculated for C13H13NO4
[M+Na]+: 270.0742, Found 270.0839.
N
-Isopropyl-8-methoxy-2-oxo-2 -chromene-3-carboxamide (3n).
H
Yield- 75%, colorless crystalline solid, M.P. 125-127 °C; 1H NMR (300
MHz, CDCl3): δ 1.28 (d, J= 6.6 Hz, 6H, 2×CH3), 3.99 (s, 3H, OCH3),
4.23-4.30 (m, 1H, CH), 7.17-7.32 (m, 3H, ArH), 8.69 (br. s, 1H, NH),
8.88 (s, 1H, H-4); 13C NMR (75 MHz, CDCl3): δ 22.4, 41.7, 56.1, 115.2, N,N-Tetramethylene-2-oxo-2
H
-chromene-3-carboxamide
(5c).
118.6, 119.1, 120.4, 124.5, 144.6, 146.8, 148.1, 160.3, 160.7; HRMS: Yield- 68%, colorless crystalline solid, M.P. 140-142 °C; IR (KBr
m/z calculated for C14H15NO4 [M+H]+: 262.1079, Found 262.1628.
-Cyclohexyl-2-oxo-2 -chromene-3-carboxamide (3o). Yield- 82 %,
colorless crystalline solid, M.P. 176-178 °C; 1H NMR (300 MHz,
CDCl3): δ 1.24-1.45 (m, 6H,-CH2-CH2-CH2-), 1.73-1.77 (m, 2H,-NH-CH-
CH2-), 1.78-2.00 (m, 2H,-NH-CH-CH2-), 3.94-4.03 (m, 2H, -NH-CH-
CH2-), 7.34-7.42 (m, 2H, H-6, H-8), 7.62-7.70 (m, 2H, H-5, H-7), 8.76
(br. s, 1H, NH), 8.90 (s, 1H, H-4); 13C NMR (75 MHz, CDCl3): δ 24.7,
25.6, 32.7, 48.5, 116.6, 118.7, 118.8, 125.2, 129.7, 133.8, 148.1,
pellet): 3423, 3053, 2971, 2875, 1723,620, 1627, 1570, 1425, 1337,
1192, 1049, 763, 971, 925, 806 cm-1; 1H NMR (300 MHz, CDCl3): δ
1.91-2.00 (m, 4H, -CH2-CH2-), 3.46 (t, J = 6.0 Hz, 2H, >N-CH2-), 3.64
(t, J = 6.0 Hz, 2H, >N-CH2-), 7.29-7.37 (m, 2H, H-6, H-8), 7.53-7.62
(m, 2H, H-5, H-7), 7.97 (s, 1H, H-4); 13C NMR (75 MHz, CDCl3): δ
24.2, 26.0, 46.2, 47.5, 116.7, 118.3, 124.9, 126.2, 128.6, 132.8,
143.1, 154.1, 157.7, 163.2; HRMS: m/z calculated for C14H13NO3
[M+Na]+: 266.0793, Found 266.1015.
N
H
6 | J. Name., 2012, 00, 1-3
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