S. Periyaraja, P. Shanmugam, A. B. Mandal
FULL PAPER
H), 7.55 (d, J = 8.5 Hz, 2 H) ppm. 13C NMR (125.7 MHz, CDCl3/
TMS): δ = 21.6, 27.3, 62.5, 70.7, 109.7, 110.2, 117.5, 118.3, 119.2,
119.9, 121.2, 122.2, 124.2, 124.4, 125.9, 127.0, 127.1, 128.1, 128.3,
128.6, 128.9, 129.3, 129.4, 129.5, 129.9, 136.6, 138.9, 142.2, 143.2,
144.6, 163.2, 172.9 ppm. HRMS: calcd. for C31H25F3N3O4S [M +
H]+ 592.1518; found 592.1521.
122.9, 125.3, 126.0, 127.1, 127.3, 127.8, 128.4, 128.5, 128.7, 129.1,
129.4, 129.9, 130.3, 133.6, 136.8, 138.0, 139.5, 139.9, 140.5, 142.9,
1 4 3 . 1 , 1 6 3 . 8 p p m . H R M S : c a l c d . fo r C 3 4 H 2 5 N 2 O 2 S
[M + H]+ 527.1793; found 527.1793.
(R)-N-(1Ј,3Ј-Dioxo-1,3-diphenyl-1Ј,3Ј-dihydrospiro[azetidine-2,2Ј-
indene]-4-ylidene)-4-methylbenzenesulfonamide (5m): White powder
4-Methyl-N-{(2S,3S)-1Ј-methyl-2Ј-oxo-1-p-tolyl-3-[4-(trifluoro-
methyl)phenyl]spiro(azetidine-2,3Ј-indoline)-4-ylidene}benzene-
sulfonamide (4k): White powder (29 mg, 10% yield). FTIR (KBr):
(182 mg, 72% yield). FTIR (KBr): ν
= 3450, 3.61, 2924, 1751,
˜
max
1718, 1632, 1595, 1498, 1458, 1410, 1314, 1226, 1154, 1090, 882,
755, 728, 694, 554, 530 cm–1. 1H NMR (500.1 MHz, CDCl3/TMS):
δ = 2.40 (s, 3 H), 5.26 (s, 1 H), 7.06 (d, J = 7.5 Hz, 1 H), 7.11–7.14
(m, 1 H), 7.17–7.29 (m, 10 H), 7.54 (d, J = 7.5 Hz, 2 H), 7.75 (d,
J = 7.5 Hz, 1 H), 7.90 (t, J = 7.5 Hz, 1 H), 7.98 (t, J = 7.5 Hz, 1
H), 8.14 (d, J = 7.5 Hz, 1 H) ppm. 13C NMR (125.7 MHz, CDCl3/
TMS): δ = 21.6, 62.7, 74.1, 118.1, 124.2, 124.4, 126.1, 127.0, 128.6,
128.9, 129.1, 129.7, 129.2, 129.3, 129.4, 129.9, 136.2, 137.2, 137.6,
138.6, 139.7, 140.4, 143.1, 162.1, 191.6, 193.6 ppm. HRMS: calcd.
for C30H23N2O4S [M + H]+ 507.1378; found 507.1374.
ν
max = 3439, 3063, 2987, 2927, 1730, 1632, 1515, 1471, 1324, 1247,
˜
1155, 1121, 1091, 1069, 922, 861, 815, 754, 685, 661, 540 cm–1; H
NMR (500.1 MHz, CDCl3/TMS): δ = 2.25 (s, 3 H), 2.40 (s, 3 H),
3.06 (s, 3 H), 5.28 (s, 1 H), 6.9 (d, J = 8 Hz, 1 H), 7.03 (d, J =
8.5 Hz, 2 H), 7.13 (t, J = 8.5 Hz, 4 H), 7.18 (t, J = 8 Hz, 1 H), 7.24
(d, J = 8.5 Hz, 2 H), 7.37 (d, J = 8 Hz, 2 H), 7.45 (d, J = 8 Hz, 3
H), 7.50 (d, J = 7 Hz, 1 H) ppm. 13C NMR (125.7 MHz, CDCl3/
TMS): δ = 21.0, 21.5, 26.9, 63.6, 71.2, 109.4, 118.4, 122.9, 123.7,
123.8, 123.9, 124.8, 124.9, 125.1, 125.1, 126.6, 129.2, 129.9, 130.1,
130.2, 130.5, 131.6, 133.6, 133.9, 136.0, 138.7, 143.1, 143.2, 162.6,
169.4 ppm. HRMS: calcd. for C31H27F3N3O3S [M + H]+ 590.1725;
found 590.1734.
1
4-Methyl-N-[(1ЈS,2R,3S,4ЈR)-1Ј,7Ј,7Ј-trimethyl-3Ј-oxo-1,3-diphenyl-
spiro(azetidine-2,2Ј-bicyclo[2.2.1]heptane)-4-ylidene]benzenesulfon-
amide (4n): White powder (51 mg, 20% yield). FTIR (KBr): ν
˜
max
= 3430, 3063, 3035, 2965, 2934, 2875, 1744, 1627, 1593, 1454, 1408,
4-Methyl-N-{(2S,3R)-1Ј-methyl-2Ј-oxo-1-p-tolyl-3-[4-(trifluoro-
methyl)phenyl]spiro(azetidine-2,3Ј-indoline)-4-ylidene}benzene-
sulfonamide (5k): White powder (212 mg, 72% yield). FTIR (KBr):
1
1310, 1154, 1091, 1008, 915, 881, 827, 768, 734, 684, 553 cm–1. H
NMR (500.1 MHz, CDCl3/TMS): δ = 0.79 (s, 3 H), 0.84 (s, 3 H),
0.95 (s, 3 H), 1.22–1.28 (m, 1 H), 1.29–1.34 (m, 1 H), 1.54–1.59 (m,
1 H), 1.61–1.67 (m, 1 H), 2.27 (s, 3 H), 2.61 (d, J = 4.5 Hz, 1 H),
4.94 (s, 1 H), 6.89 (s, 4 H), 7.28 (t, J = 6.5 Hz, 3 H), 7.33–7.37 (m,
5 H), 7.45 (d, J = 7.5 Hz, 2 H) ppm. 13C NMR (125.7 MHz,
CDCl3/TMS): δ = 9.6, 18.9, 20.9, 21.5, 22.3, 31.3, 45.0, 55.5, 60.2,
65.2, 81.7, 124.5, 126.5, 127.9, 128.1, 128.3, 128.6, 128.8, 129.5,
130.8, 137.2, 138.5, 142.2, 166.8, 213.1 ppm. HRMS: calcd. for
C31H33N2O3S [M + H]+ 513.2212; found 513.2226.
ν
max = 3435, 3063, 2925, 1731, 1633, 1614, 1517, 1406, 1371, 1251,
˜
1158, 1115, 1091, 1068, 1018, 918, 834, 812, 754, 731, 709, 662,
1
550, 537 cm–1. H NMR (500.1 MHz, CDCl3/TMS): δ = 2.21 (s, 3
H), 2.41 (s, 3 H), 3.34 (s, 3 H), 5.37 (s, 1 H), 6.59 (d, J = 7.5 Hz,
1 H), 6.71 (t, J = 7.5 Hz, 1 H), 6.89 (d, J = 7.5 Hz, 1 H), 6.98 (d,
J = 8.5 Hz, 2 H), 7.05 (d, J = 7.05 Hz, 2 H), 7.22–7.28 (m, 5 H),
7.47 (d, J = 8.5 Hz, 2 H), 7.75 (d, J = 7.5 Hz, 2 H) ppm. 13C NMR
(125.7 MHz, CDCl3/TMS): δ = 21.0, 21.6, 27.2, 61.5, 70.9, 109.2,
118.4, 120.3, 122.8, 123.1, 125.0, 125.6, 125.7, 125.9, 126.7, 126.9,
129.0, 129.2, 129.4, 130.2, 131.4, 134.1, 135.9, 136.7, 139.1, 143.2,
143.7, 143.7, 162.4, 172.7 ppm. HRMS: calcd. for C31H27F3N3O3S
[M + H]+ 590.1725; found 590.1731.
4-Methyl-N-[(1ЈS,2R,3R,4ЈR)-1Ј,7Ј,7Ј-trimethyl-3Ј-oxo-1,3-diphen-
ylspiro(azetidine-2,2Ј-bicyclo[2.2.1]heptane)-4-ylidene]benzene-
sulfonamide (5n): White powder (184 mg, 72% yield). FTIR (KBr):
ν
˜
max = 3469, 3092, 3004, 3034, 2875, 1748, 1632, 1592, 1495, 1453,
1420, 1305, 1152, 1090, 1003, 914, 880, 833, 768, 686, 539 cm–1. 1H
NMR (500.1 MHz, CDCl3/TMS): δ = 0.07 (s, 3 H), 0.61 (s, 3 H),
0.83 (s, 3 H), 0.85–0.89 (m, 1 H), 1.38–1.40 (m, 1 H), 2.06–2.12 (m,
1 H), 2.29 (s, 3 H), 2.53 (d, J = 4 Hz, 1 H), 5.23 (s, 1 H), 6.97 (d,
J = 8.5 Hz, 2 H), 7.14–7.18 (m, 5 H), 7.22 (d, J = 7 Hz, 1 H), 7.26–
7.28 (m, 4 H), 7.32–7.36 (m, 3 H) ppm. 13C NMR (125.7 MHz,
CDCl3/TMS): δ = 9.3, 19.9, 21.5, 21.6, 25.4, 26.6, 46.2, 51.6, 57.5,
60.7, 82.3, 126.6, 128.0, 128.1, 128.8, 129.3, 129.5, 129.8, 129.9,
131.3, 135.2, 139.3, 143.1, 168.8, 211.1 ppm. HRMS: calcd. for
C31H33N2O3S [M + H]+ 513.2212; found 513.2196.
(R)-N-(1,3-Diphenylspiro[azetidine-2,9Ј-fluorene]-4-ylidene)-4-meth-
ylbenzenesulfonamide (5l): White powder (236 mg, 90 % yield).
FTIR (KBr): ν
= 3427, 3060, 2924, 2856, 1621, 1496, 1458,
˜
max
1408, 1311, 1241, 1155, 1091, 910, 808, 748, 686, 544 cm–1 1H
.
NMR (500.1 MHz, CDCl3/TMS): δ = 2.40 (s, 3 H), 5.44 (s, 1 H),
6.77 (d, J = 3.5 Hz, 2 H), 6.91–6.96 (m, 3 H), 7.02 (t, J = 7.5 Hz,
2 H), 7.06–7.10 (m, 3 H), 7.14 (d, J = 8.5 Hz, 2 H), 7.17–7.21 (m,
1 H), 7.26 (d, J = 7.5 Hz, 2 H), 7.28–7.31 (m, 1 H), 7.43 (t, J =
7.5 Hz, 1 H), 7.52 (d, J = 7.0 Hz, 1 H), 7.61 (d, J = 7.5 Hz, 1 H),
7.72 (d, J = 6.5 Hz, 1 H), 7.81 (d, J = 8.5 Hz, 2 H) ppm. 13C NMR
(125.7 MHz, CDCl3/TMS): δ = 21.7, 63.6, 76.7, 118.8, 120.5, 120.9,
122.9, 125.3, 126.0, 127.1, 127.3, 127.8, 128.4, 128.5, 128.7, 129.1,
129.4, 129.9, 130.3, 133.6, 136.8, 138.0, 139.5, 139.9, 140.5, 142.9,
1 4 3 . 1 , 1 6 3 . 8 p p m . H R M S : c a l c d . fo r C 3 4 H 2 5 N 2 O 2 S
[M + H]+ 527.1793; found 527.1793.
(S)-N-[1Ј-(4-Chlorophenyl)-2-oxo-3Ј-phenyl-2H-spiro(acenaphth-
ylene-1,2Ј-azetidine)-4Ј-ylidene]-4-methylbenzenesulfonamide (4o):
White powder (207 mg, 74 % yield). FTIR (KBr): ν
= 3434,
˜
max
3057, 2924, 1730, 1634, 1494, 1401, 1313, 1153, 1014, 931, 857,
1
834, 733, 691, 552 cm–1. H NMR (500.1 MHz, CDCl3/TMS): δ =
(R)-N-(1,3-Diphenylspiro[azetidine-2,9Ј-fluorene]-4-ylidene)-4-meth-
ylbenzenesulfonamide (5l): White powder (236 mg, 90 % yield).
2.43 (s, 2 H), 2.44 (s, 3 H), 5.32 (s, 1 H), 5.40 (s, 1 H), 7.04 (s, 2
H), 7.08–7.17 (m, 8 H), 7.19 (d, J = 8.5 Hz, 2 H), 7.23 (t, J = 8 Hz,
FTIR (KBr): ν
= 3427, 3060, 2924, 2856, 1621, 1496, 1458, 1 H), 7.28–7.30 (m, 2 H), 7.54 (d, J = 7.5 Hz, 2 H), 7.43–7.79 (m,
˜
max
1408, 1311, 1241, 1155, 1091, 910, 808, 748, 686, 544 cm–1
.
1H
5 H), 7.82–7.86 (m, 1 H), 8.04 (t, J = 4.5 Hz, 1 H), 8.14 (d, J =
7.0 Hz, 1 H), 8.19–8.23 (m, 1 H) ppm. 13C NMR (125.7 MHz,
CDCl3/TMS): δ = 21.7, 22.6, 62.5, 65.5, 75.6, 75.7, 119.6, 119.7,
NMR (500.1 MHz, CDCl3/TMS): δ = 2.40 (s, 3 H), 5.44 (s, 1 H),
6.77 (d, J = 3.5 Hz, 2 H), 6.91–6.96 (m, 3 H), 7.02 (t, J = 7.5 Hz,
2 H), 7.06–7.10 (m, 3 H), 7.14 (d, J = 8.5 Hz, 2 H), 7.17–7.21 (m, 120.4, 122.9, 123.3, 123.4, 126.5, 126.9, 127.1, 128.2, 128.3, 128.4,
1 H), 7.26 (d, J = 7.5 Hz, 2 H), 7.28–7.31 (m, 1 H), 7.43 (t, J = 128.5, 128.6, 128.7, 128.9, 129.0, 129.2, 129.3, 129.5, 130.5, 130.6,
7.5 Hz, 1 H), 7.52 (d, J = 7.0 Hz, 1 H), 7.61 (d, J = 7.5 Hz, 1 H), 130.7, 130.8, 130.9, 132.7, 132.8, 133.5, 134.9, 135.5, 140.9, 141.8,
7.72 (d, J = 6.5 Hz, 1 H), 7.81 (d, J = 8.5 Hz, 2 H) ppm. 13C NMR 143.2, 143.3, 163.7, 163.8, 195.9, 199.3 ppm. HRMS: calcd. for
(125.7 MHz, CDCl3/TMS): δ = 21.7, 63.6, 76.7, 118.8, 120.5, 120.9, C33H24ClN2O3S [M + H]+ 563.1196; found 563.1210.
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Eur. J. Org. Chem. 2014, 954–965