6
Tetrahedron
4.2.15(Z)-4-Methyl-N-(3-(3-(trifluoromethyl)phenyl)-2H-
116.13, 111.54, 21.67.; HRMS Mass Chemical Formula:
ACCEPTED MANUSCRIPT
chromen-2-ylidene)benzenesulfonamide : 3ab
C22H17N2O5S [M + H]+: 421.0853; Found: 421.0863.
The obtained residue after work up was purified by column
chromatography over silica gel using EtOAc/petroleum ether
(20:80) to furnish the pure compound 3ab 100 mg scale reaction
(371 mg, 87%) as pale brown solid, m.p.175-176°C; IR (ν/cm-1):
4.2.19 (Z)-N-(6-Chloro-3-phenyl-2H-chromen-2-ylidene)-4-
methylbenzenesulfonamide : 3af
The obtained residue after work up was purified by column
chromatography over silica gel using EtOAc/petroleum ether
(15:85) to furnish the pure compound 3af 100 mg scale reaction
(190 mg, 72%) as yellow solid, m.p.162-163°C; IR (ν/cm-1):
1
3056, 2852, 1627, 1557, 1303, 1152, 1085, 694.; H-NMR (400
MHz, CDCl3) δ: 7.93 – 7.82 (m, 3H), 7.81 – 7.73 (m, 2H), 7.66 –
7.46 (m, 5H), 7.37 (t, J = 7.4 Hz, 1H), 7.27 (d, J = 7.5 Hz, 2H),
2.39 (s, 3H).; 13C-NMR (100 MHz, CDCl3) δ: 156.82, 152.45,
143.15, 140.15, 139.05, 135.12, 132.47, 132.38, 129.22, 128.79,
128.61, 128.30, 126.98, 125.99, 125.95, 125.89, 125.65, 125.61,
119.42, 116.69, 21.51.; HRMS Mass Chemical Formula:
C23H17F3NO3S [M + H]+: 444.0876; Found: 444.0876.
1
3066, 1640, 1510, 1450, 1324, 1120, 1085, 756.; H-NMR (400
MHz, CDCl3) δ: 7.89 (d, J = 8.2 Hz, 2H), 7.61 – 7.52 (m, 2H),
7.47 (dd, J = 5.1, 2.2 Hz, 1H), 7.38 (dd, J = 10.7, 7.7 Hz, 2H),
7.26 (d, J = 8.2 Hz, 1H), 2.38 (s, 3H).; 13C-NMR (100 MHz,
CDCl3) δ: 150.55, 143.17, 139.00, 137.98, 133.94, 131.72,
131.36, 130.98, 129.26, 129.22, 129.01, 128.29, 127.23, 127.11,
120.82, 117.88, 21.54.; HRMS Mass Chemical Formula:
C22H17ClNO3S [M + H]+: 410.0612; Found: 410.0589.
4.2.16
(Z)-N-(3-(4-Chlorophenyl)-2H-chromen-2-ylidene)-4-
methylbenzenesulfonamide : 3ac
The obtained residue after work up was purified by column
chromatography over silica gel using EtOAc/petroleum ether
(20:80) to furnish the pure compound 3ac 100 mg scale reaction
(263 mg, 78%) as white solid, m.p.161-162°C; IR (ν/cm-1): 3070,
4.2.20 (Z)-N-(6-chloro-3-(4-nitrophenyl)-2H-chromen-2-
ylidene)-4-methylbenzene sulfonamide : 3ag
The obtained residue after work up was purified by column
chromatography over silica gel using EtOAc/petroleum ether
(35:65) to furnish the pure compound 3ag 100 mg scale reaction
(179 mg, 61%) as yellow solid, m.p.189-190°C; IR (ν/cm-1):
3096, 2942, 1592, 1468, 1342, 1191, 1084, 841.; 1H-NMR (400
MHz, CDCl3) δ: δ 8.29 (dd, J = 8.6, 3.2 Hz, 2H), 8.03 (d, J = 2.3
Hz, 1H), 7.91 – 7.82 (m, 1H), 7.68 (d, J = 8.7 Hz, 2H), 7.54 (dd,
J = 19.4, 5.8 Hz, 3H), 7.46 – 7.30 (m, 1H), 7.17 (dd, J = 16.8, 8.4
Hz, 2H), 2.33 (s, 3H).; 13C-NMR (100 MHz, CDCl3) δ: 148.29,
147.95, 146.58, 146.33, 140.22, 139.07, 137.05, 133.58, 132.33,
131.27, 130.31, 129.49, 128.57, 128.36, 126.82, 125.24, 124.31,
123.69, 118.10, 115.57, 112.84, 21.69.; HRMS Mass Chemical
Formula: C22H15ClN2NaO5S [M + Na]+: 477.0282; Found:
477.0282.
1
2592, 1628, 1557, 1489, 1293, 1139, 1088, 835.; H-NMR (400
MHz, CDCl3) δ: 7.92 (d, J = 7.2 Hz, 2H), 7.79 (d, J = 7.2 Hz,
2H), 7.68 (s, 1H), 7.53 (dd, J = 12.9, 5.7 Hz, 3H), 7.45 (d, J = 8.3
Hz, 1H), 7.31 (dd, = 25.6, 8.1 Hz, 5H).; 13C-NMR (100 MHz,
CDCl3) δ: 157.06, 152.29, 143.19, 139.66, 139.00, 135.04,
132.75, 132.17, 130.37, 129.66, 129.24, 128.88, 128.48, 128.20,
127.22, 126.42, 125.83, 119.57, 116.47, 21.55.; HRMS Mass
Chemical Formula: C22H17ClNO3S [M + H]+: 410.0612; Found:
410.0592.
4.2.17 (Z)-4-Methyl-N-(3-(p-tolyl)-2H-chromen-2-
ylidene)benzene sulfonamide : 3ad
The obtained residue after work up was purified by column
chromatography over silica gel using EtOAc/petroleum ether
(20:80) to furnish the pure compound 3ad 100 mg scale reaction
(240 mg, 75%) as pale brown solid, m.p.196-197°C; IR (ν/cm-1):
4.2.21 (Z)-N-(7-(diethylamino)-3-(4-nitrophenyl)-2H-chromen-2-
ylidene)-4-methylbenzenesulfonamide : 3ah
1
3080, 1622, 1540, 1451, 1301, 1150, 1085, 818, 749.; H-NMR
The obtained residue after work up was purified by column
chromatography over silica gel using EtOAc/petroleum ether
(35:65) to furnish the pure compound 3ah 100 mg scale reaction
(170 mg, 67%) as orange solid, m.p.185-168°C; IR (ν/cm-1):
2889, 1615, 1572, 1406, 1373, 1265, 1169, 1072, 841.; 1H-NMR
(400 MHz, CDCl3) δ: 8.19 (dd, J = 12.8, 9.1 Hz, 3H), 7.57 (dd, J
= 32.8, 8.6 Hz, 4H), 7.37 (s, 1H), 7.11 (d, J = 8.2 Hz, 2H), 6.60
(dd, J = 9.2, 2.6 Hz, 1H), 6.44 (d, J = 2.6 Hz, 1H), 3.37 (q, J =
7.1 Hz, 4H), 2.27 (s, 3H), 1.17 (t, J = 7.1 Hz, 6H).; 13C-NMR
(100 MHz, CDCl3) δ: 151.11, 150.90, 146.88, 145.79, 141.38,
138.01, 131.83, 129.99, 129.49, 128.30, 125.58, 124.06, 117.95,
113.00, 110.16, 105.84, 102.70, 44.84, 21.60, 12.45.; HRMS
Mass Chemical Formula: C26H26N3O5S [M + H]+: 492.1588;
Found: 492.1591.
(400 MHz, CDCl3) δ: 7.94 (d, J = 8.2 Hz, 2H), 7.67 (s, 1H), 7.59
– 7.42 (m, 5H), 7.37 – 7.26 (m, 3H), 7.19 (d, J = 7.9 Hz, 2H),
2.38 (d, J = 8.0 Hz, 6H).; 13C-NMR (100 MHz, CDCl3) δ:
157.49, 152.18, 142.95, 139.26, 139.05, 139.02, 131.69, 131.45,
130.07, 129.16, 128.95, 128.92, 128.00, 127.26, 125.64, 119.86,
116.40, 21.53, 21.29.; HRMS Mass Chemical Formula:
C23H20NO3S [M + H]+: 390.1158; Found: 390.1139.
4.2.18 (Z)-4-Methyl-N-(3-(4-nitrophenyl)-2H-chromen-2-ylidene)
benzenesulfonamide : 3ae
The obtained residue after work up was purified by column
chromatography over silica gel using EtOAc/petroleum ether
(20:80) to furnish the pure compound 3ae 100 mg scale reaction
(272 mg, 79%) as yellow solid, m.p.197-198°C; IR (ν/cm-1):
3111, 2851, 1591, 1517, 1448, 1339, 1166, 1086, 881.; 1H-NMR
(400 MHz, CDCl3) δ: 8.28 (d, J = 8.9 Hz, 2H), 8.09 (d, J = 7.0
Hz, 1H), 7.68 (d, J = 8.9 Hz, 2H), 7.62 (s, 1H), 7.55 (d, J = 8.3
Hz, 2H), 7.52 – 7.38 (m, 2H), 7.27 (d, J = 8.1 Hz, 1H), 7.12 (d, J
= 8.1 Hz, 2H), 2.32 (s, 3H).; 13C-NMR (100 MHz, CDCl3) δ:
148.26, 148.06, 147.77, 146.05, 139.54, 138.59, 132.63, 131.51,
130.19, 128.84, 128.33, 127.79, 127.15, 126.66, 124.25, 124.00,
4.2.22 N-(3-(2-hydroxyphenyl)-2-phenylpropyl)-4-methylbenzene
sulfonamide: 5b
The compound 4a (200 mg) was dissolved in MeOH (25 mL)
and cooled to 0 °C on an ice-water bath. NaBH4 (0.180 g, 5.3
mmol) was then added in portion to the reaction mixture and
stirred at 0 °C for 3 hours. Then, solvent was evaporated under
reduced pressure and residue partitioned between ethyl acetate
(50 mL) and water (30 mL). Water layer was separated and ethyl