The Journal of Organic Chemistry
Page 12 of 14
145.0, 144.7, 134.4, 130.2, 127.2, 97.3, 32.2, 29.7; IR (NaCl): 3099, 2963, 1682, 1621, 1600, 1433, 1367, 1352; HRMS
(ESI): m/z calcd for C11H13NO4S: 278.0458 [M+Na]+, found: 278.0458.
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(E)ꢀN,4ꢀDimethylꢀNꢀ(2ꢀ(phenylsulfonyl)vinyl)benzenesulfonamide (3ig). This compound was obtained as a white solid
(35.8mg, 51%) by following general procedure: mp 147ꢀ149 °C;
1H NMR (400 MHz, CDCl3) δ 8.18 (d, J = 13.4 Hz, 1H),
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7.90 (d, J = 7.6 Hz, 2H), 7.72 (d, J = 8.2 Hz, 2H), 7.61 (t, J = 7.2 Hz, 1H), 7.54 (t, J = 7.5 Hz, 2H), 7.38 (d, J = 8.1 Hz, 2H),
5.52 (d, J = 13.4 Hz, 1H), 2.93 (s, 3H), 2.47 (s, 3H); 13C NMR (,100 MHz, CDCl3) δ 145.4, 142.0, 141.7, 134.0, 133.0,
130.4, 129.3, 127.3, 127.1, 107.8, 32.5, 21.7; IR (NaCl): 3077, 2928, 1614, 1447, 1367; HRMS (ESI): m/z calcd for
C16H17NO4S2: 374.0492 [M+Na]+, found: 374.0493.
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(E)ꢀDimethyl (2ꢀ(N,4ꢀdimethylphenylsulfonamido)vinyl)phosphonate (3ih). This compound was obtained as a colorless
sticky oil (37.0mg, 58%) by following general procedure; 1H NMR (400 MHz, CDCl3) δ 7.82 (dd, J = 16.5, 15.4 Hz, 1H),
7.69 (d, J = 8.2 Hz, 2H), 7.35 (d, J = 8.1 Hz, 2H), 4.57 (dd, J = 15.2, 11.4 Hz, 1H), 3.73 (d, J = 11.2 Hz, 6H), 2.95 (s, 3H),
2.44 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 144.9, 144.8 (J = 19.5), 134.5, 130.2, 127.1, 89.7 (J = 202.7), 52.4 (J = 5.6),
31.7, 21.6; 31P NMR (CDCl3, 162 MHz) δ 23.8; IR (NaCl): 2953, 2871, 1614, 1457, 1362; HRMS (ESI): m/z calcd for
C12H18NO5PS: 342.0536 [M+Na]+, found: 342.0547.
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N,4ꢀDimethylꢀNꢀ(3ꢀoxopentyl)benzenesulfonamide (4ii). This compound was obtained as a colorless sticky oil (39.9mg, 74%)
by following general procedure;
1H NMR (400 MHz, CDCl3) δ 7.68 (d, J = 8.2 Hz, 2H), 7.33 (d, J = 8.1 Hz, 2H), 3.27 (t, J =
7.0 Hz, 2H), 2.80ꢀ 2.73 (m, 5H), 2.48 (t, J = 7.3 Hz, 2H), 2.44 (s, 3H), 1.07 (t, J = 7.3 Hz, 3H); 13C NMR (100 MHz, CDCl3)
δ 209.5, 143.5, 134.1, 129.8, 127.5, 45.4, 41.6, 36.3, 36.1, 21.5, 7.6; IR (NaCl): 2977, 2938, 1715, 1597, 1457, 1378, 1339;
HRMS (ESI): m/z calcd for C13H19NO3S: 292.0978 [M+Na]+, found: 292.0986.
Methyl (E)ꢀ3ꢀ((Nꢀbutylꢀ4ꢀmethylphenyl)sulfonamido)acrylate (3ja). This compound was obtained as a white solid (42.4mg,
68%) by following general procedure: mp 71ꢀ72 °C;
1H NMR (400 MHz, CDCl3) δ 8.12 (d, J = 14.0 Hz, 1H), 7.71 (d, J =
8.0 Hz, 2H), 7.35 (d, J = 8.0 Hz, 2H), 5.08 (d, J = 14.0 Hz, 1H), 3.75 (s, 3H), 3.42 – 3.30 (m, 2H), 2.46 (s, 3H), 1.57 (t, J =
7.9 Hz, 2H), 1.40 – 1.24 (m, 2H), 0.92 (t, J = 7.4 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 167.6, 144.7, 142.0, 135.5, 130.1,
127.1, 97.4, 51.4, 46.0, 28.7, 21.6, 20.0, 13.6; IR (NaCl): 2958, 2875, 1715, 1622, 1457, 1367; HRMS (ESI): m/z calcd for
C15H21NO4S: 334.1084 [M+Na]+, found: 334.1089.
(E)ꢀMethyl 3ꢀ(Nꢀ(2ꢀmethoxyꢀ2ꢀoxoethyl)ꢀ4ꢀmethylphenylsulfonamido)acrylate (3ka). This compound was obtained as a white
solid (40.6mg, 62%) by following general procedure: mp 146ꢀ148 °C;
1H NMR (400 MHz, CDCl3) δ 8.10 (d, J = 13.9 Hz,
1H), 7.76 (d, J = 8.0 Hz, 2H), 7.37 (d, J = 8.0 Hz, 2H), 4.95 (d, J = 14.0 Hz, 1H), 4.30 (s, 2H), 3.73 (s, 3H), 3.65 (s, 3H),
2.46 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 167.0, 166.8, 145.2, 141.5, 135.0, 130.0, 127.6, 98.4, 52.7, 51.5, 46.7, 21.7; IR
(KBr): 3104, 2953, 2849, 1753, 1717, 1630 1598, 1498, 1428, 1375, 1301; HRMS (ESI): m/z calcd for C14H17NO6S:
350.0669 [M+Na]+, found: 350.0678.
Ethyl (E)ꢀ3ꢀ((Nꢀ(2ꢀbromoethyl)ꢀ4ꢀmethylphenyl)sulfonamido)acrylate (3mb). This compound was obtained as a white solid
(15.0mg, 20%) by following general procedure: mp 68ꢀ70 °C;
1H NMR (400 MHz, CDCl3) δ 8.04 (d, J = 14.1 Hz, 1H), 7.70
(d, J = 8.3 Hz, 2H), 7.35 (d, J = 8.0 Hz, 2H), 5.14 (d, J = 14.1 Hz, 1H), 4.19 (d, J = 7.1 Hz, 2H), 3.70 (dd, J = 9.2, 7.1 Hz,
2H), 3.39 (dd, J = 9.1, 7.1 Hz, 2H), 2.44 (s, 3H), 1.28 (t, J = 7.1 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 166.7, 145.3, 140.9,
134.8, 130.4, 127.2, 98.4, 60.4, 47.0, 25.5, 21.6, 14.4; IR(KBr): 3072, 2984, 2939, 1723, 1631, 1597, 1451, 1374; HRMS
(ESI): m/z calcd for C14H18BrNO4S: 398.0033 [M+Na]+, found: 398.0042.
(E)ꢀMethyl 3ꢀ(Nꢀ(4ꢀfluorobenzyl)ꢀ4ꢀmethylphenylsulfonamido)acrylate (3oa). This compound was obtained as a white solid
(48.0mg, 66%) by following general procedure: mp 93ꢀ94 °C;
1H NMR (400 MHz, CDCl3) δ 8.18 (d, J = 13.9 Hz, 1H), 7.73
(d, J = 7.9 Hz, 2H), 7.36 (d, J = 7.9 Hz, 2H), 7.22 (dd, J = 8.3, 5.2 Hz, 2H), 7.01 (t, J = 8.5 Hz, 2H), 4.97 (d, J = 14.0 Hz,
1H), 4.58 (s, 2H), 3.69 (s, 3H), 2.47 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 167.2, 162.3 (J = 245.2), 145.1, 141.6, 135.2,
130.2, 129.6 (J = 3.2), 128.5 (J = 8.1), 127.2, 115.8 (J = 21.6), 99.4, 51.4, 49.1, 21.7; 19F NMR (376 MHz, CDCl3) δ ꢀ114.24;
IR (KBr): 3010, 3069, 2947, 2851, 1706, 1622, 1509, 1434, 1362; HRMS (ESI): m/z calcd for C18H18FNO4S: 386.0833
[M+Na]+, found: 386.0840.
1ꢀTosylꢀ2,3,5,6,7,7aꢀhexahydroꢀ1Hꢀindole (7v): This compound was obtained as a white solid (12.8mg, 23%) by following
general procedure: mp 78ꢀ80 °C;
1H NMR (400 MHz, CDCl3) δ 7.75 (d, J = 8.2 Hz, 2H), 7.34 (d, J = 7.9 Hz, 2H), 5.51 (t, J
= 3.1 Hz, 1H), 3.60 – 3.50 (m, 1H), 3.43 – 3.35 (m, 1H), 3.34 – 3.26 (m, 1H), 2.57 – 2.48 (m, 1H), 2.45 (s, 3H), 2.30 – 2.20
(m, 1H), 2.10 – 1.96 (m, 3H), 1.89 – 1.80 (m, 1H), 1.55 – 1.30 (m, 2H); 13C NMR (100 MHz, CDCl3) δ 143.3, 137.4, 134.6,
129.6, 127.6, 121.1, 58.7, 58.7, 47.6, 29.9, 24.3, 21.5, 20.2; IR (KBr): 3028, 2927, 1598, 1494, 1478, 1455, 1401, 1337;
HRMS (ESI): m/z calcd for C15H19NO2S: 300.1029 [M+Na]+, found: 300.1034.
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