D. Sureshkumar, S. Koutha, S. Chandrasekaran
FULL PAPER
(
1
1
d, J = 8.1 Hz, 2 H), 5.33 (d, J = 15.3 Hz, 1 H), 4.64 (d, J = 8.7 Hz,
δ = 143.8, 138.2, 129.9, 126.9, 64.9, 59.2, 35.9, 35.3, 31.0, 21.5,
7
7
H), 3.69 (m, 1 H), 3.25 (dd, J = 10.8, 3.3 Hz, 1 H), 3.06 (d, J =
13.9 ppm. Se NMR (76 MHz, CDCl
(neat): ν˜ max = 3275, 1337, 1159, 1092, 814, 659 cm . HR-MS:
calcd. for C15 23NO SSe
[M + Na]+ 463.9678; found 463.9680.
3
): δ = 332.2, 205.5 ppm. IR
1
3
–1
0.8 Hz, 1 H), 2.45 (s, 3 H), 1.37 (d, J = 6.9 Hz, 3 H) ppm.
): δ = 143.8, 138.1, 129.9, 126.9, 66.2, 51.9,
4.6, 22.8, 21.6 ppm. 77Se NMR (76 MHz, CDCl
): δ = 360.4,
05.4 ppm. IR (neat): ν˜ max = 3275, 1333, 1159, 1092, 1040, 814,
C
NMR (75 MHz, CDCl
3
H
2
2
3
2
6
3
Compounds 3g and 3gЈ: R = 0.65 (EtOAc/toluene, 3:7). Yield:
.063 g, 56%. H NMR (400 MHz, CDCl ): δ = 7.77–7.74 (m, 4
H), 7.32–7.27 (m, 4 H), 5.63–5.25 (m, 2 H), 5.05 (d, J = 17.2 Hz,
H), 4.96 (d, J = 10.4 Hz, 1 H), 4.72 (d, J = 7.2 Hz, 1 H), 4.52 (t,
f
1
0
3
–1
+
2 2
58 cm . HR-MS: calcd. for C11H15NO SSe [M + Na] 407.9052;
found 407.9058.
1
Compound 3d: R
H NMR (300 MHz, CDCl
f
= 0.65 (EtOAc/toluene, 3:7). Yield: 0.082 g, 65%.
): δ = 7.75 (d, J = 8.1 Hz, 2 H), 7.31
J = 6.6 Hz, 1 H), 3.93–3.86 (m, 1 H), 3.61 (t, J = 8.4 Hz, 1 H),
2.43 (s, 3 H), 2.42 (s, 3 H), 1.54 (d, J = 6.8 Hz, 3 H), 1.16 (d, J =
1
3
1
3
(
(
(
3
1
d, J = 8.1 Hz, 2 H), 5.59–5.48 (m, 1 H), 5.36–5.26 (m, 1 H), 4.39 6.8 Hz, 3 H) ppm. C NMR (100 MHz, CDCl
t, J = 5.4 Hz, 1 H), 3.52 (t, J = 6.0 Hz, 2 H), 2.43 (s, 3 H), 1.93 138.9, 137.9, 136.9, 129.6, 128.8, 127.2, 127.1, 115.1, 51.6, 39.8,
q, J = 13.8, 6.9 Hz, 2 H), 1.37–1.22 (m, 2 H), 0.84 (t, J = 7.2 Hz, 21.5, 21.4, 12.8 ppm. IR (neat): ν˜ max = 3283, 1456, 1166, 1092, 817,
3
): δ = 143.4, 143.2,
H) ppm. 13C NMR (75 MHz, CDCl
29.7, 127.1, 124.5, 45.4, 34.1, 22.0, 21.5, 13.6 ppm. IR (neat): ν˜ max
): δ = 143.4, 137.0, 134.9,
651 cm . HR-MS: calcd. for C11
found 248.0725.
–1
H15NO
2
S [M + Na]+ 248.0721;
3
–1
=
C
3283, 1325, 1159, 1094, 813, 667 cm . HR-MS: calcd. for
Compound 4g: R
H NMR (300 MHz, CDCl ): δ = 7.79 (d, J = 8.1 Hz, 2 H), 7.32
f
= 0.65 (EtOAc/toluene, 3:7). Yield: 0.027 g, 14%.
+
13
H19NO
2
S [M + Na] 276.1034; found 276.1040.
= 0.70 (EtOAc/toluene, 3:7). Yield: 0.031 g, 15%.
H NMR (300 MHz, CDCl ): δ = 7.78 (d, J = 8.1 Hz, 2 H), 7.33
d, J = 8.1 Hz, 2 H), 5.20 (d, J = 10.2 Hz, 1 H), 4.73 (brd, J =
1
3
Compound 4d: R
f
(d, J = 8.4 Hz, 2 H), 5.21 (d, J = 9.9 Hz, 1 H), 4.97–4.73 (m, 1 H),
3.99–3.91 (m, 1 H), 3.21 (dd, J = 10.5, 3.3 Hz, 1 H), 2.84 (dd, J =
10.6, 2.4 Hz, 1 H), 2.44 (s, 3 H), 1.39 (d, J = 6.9 Hz, 3 H) ppm.
1
3
(
1
3
9.9 Hz, 1 H), 3.52–3.48 (m, 1 H), 3.19 (dd, J = 10.5, 3.6 Hz, 3 H),
C NMR (75 MHz, CDCl
3
7
): δ = 143.5, 138.3, 129.5, 126.1, 62.7,
7
3.07 (d, J = 10.5 Hz, 1 H), 2.44 (s, 3 H), 1.53–1.21 (m, 4 H), 0.83 53.7, 35.4, 23.3, 21.5 ppm. Se NMR (76 MHz, CDCl
3
): δ = 245.3,
13
(
1
(
t, J = 6.9 Hz, 3 H) ppm. C NMR (75 MHz, CDCl
38.2, 129.9, 64.9, 58.9, 38.1, 35.3, 21.5, 21.4, 13.4 ppm. 77Se NMR 654 cm . HR-MS: calcd. for C11
76 MHz, CDCl ): δ = 330.2, 203.9 ppm. IR (neat): ν˜ max = 3278, found 407.9056.
3
): δ = 143.8,
297.6 ppm. IR (neat): ν˜ max = 3280, 1335, 1163, 1096, 1039, 816,
–1
+
2 2
H15NO SSe [M + Na] 407.9052;
3
–1
1334, 1160, 1095, 816, 672 cm . HR-MS: calcd. for
Compound 3h: R
H NMR (300 MHz, CDCl ): δ = 7.70 (d, J = 8.1 Hz, 2 H), 7.37–
f
= 0.65 (EtOAc/toluene, 3:7). Yield: 0.051 g, 31%.
C
13
H19NO
2
SSe
2
[M + Na]+ 435.9365; found 435.9386.
1
3
Compound 3e: R = 0.65 (EtOAc/toluene, 3:7). Yield: 0.092 g, 69%.
H NMR (300 MHz, CDCl ): δ = 7.76 (d, J = 8.4 Hz, 2 H), 7.30
f
7.26 (m, 7 H), 5.72–5.65 (m, 1 H), 5.54–5.46 (m, 1 H), 4.43 (s, 2
H), 3.95 (d, J = 6.3 Hz, 2 H), 3.59 (d, J = 6.9 Hz, 2 H), 2.41 (s, 3
1
3
1
3
(
(
1
d, J = 8.4 Hz, 2 H), 5.59–5.49 (m, 1 H), 5.34–5.22 (m, 1 H), 4.67 H) ppm. C NMR (75 MHz, CDCl
t, J = 6.1 Hz, 1 H), 3.52 (dt, J = 6.9, 1.0 Hz, 2 H), 2.43 (s, 3 H), 130.0, 129.6, 128.4, 127.8, 127.7, 127.1, 72.5, 65.4, 40.3, 21.5 ppm.
.93–191 (m, 2 H), 1.27–1.21 (m, 4 H), 0.65 (t, J = 7.5 Hz, 3 H) IR (neat): ν˜ max = 3279, 1597, 1330, 1160, 1093, 814, 699, 665 cm .
3
): δ = 143.4, 137.7, 136.8,
–
1
13
H21NO
2
S [M + Na]+ 354.1140; found
ppm. C NMR (75 MHz, CDCl
3
): δ = 143.3, 137.0, 134.9, 129.6,
HR-MS: calcd. for C18
354.1125.
1
27.1, 124.2, 45.3, 34.7, 30.9, 22.0, 21.4, 13.8 ppm. IR (neat): ν˜ max
–1
=
C
3282, 1326, 1168, 1094, 813, 664 cm . HR-MS: calcd. for
Compound 3hЈ: R
H NMR (300 MHz, CDCl ): δ = 7.71 (d, J = 8.4 Hz, 2 H), 7.37–
f
= 0.60 (EtOAc/toluene, 3:7). Yield: 0.052 g, 32%.
+
14
H21NO
2
S [M + Na] 290.1191; found 290.1190.
= 0.70 (EtOAc/toluene, 3:7). Yield: 0.036 g, 17%.
H NMR (300 MHz, CDCl ): δ = 7.78 (d, J = 8.1 Hz, 2 H), 7.32
d, J = 8.1 Hz, 2 H), 5.23 (d, J = 9.9 Hz, 1 H), 3.50–3.45 (m, 1 H),
1
3
Compound 4e: R
f
7.21 (m, 7 H), 5.75–5.63 (m, 1 H), 5.19–5.07 (m, 2 H), 5.01 (d, J
= 6.6 Hz, 1 H), 4.40 (s, 3 H), 3.96–3.88 (m, 1 H), 3.44–3.35 (m, 2
1
3
1
3
(
H) ppm. C NMR (75 MHz, CDCl
3
): δ = 143.2, 137.6, 137.4,
3
2
6
1
.20 (dd, J = 11.1, 3.6 Hz, 1 H), 3.08 (dd, J = 11.1, 2.1 Hz, 1 H),
135.1, 129.5, 128.4, 127.8, 127.6, 127.2, 117.4, 73.1, 71.7, 55.7,
–
1
.44 (s, 3 H), 1.57–1.35 (m, 3 H), 1.28–1.19 (m, 3 H), 0.85 (t, J = 21.5 ppm. IR (neat): ν˜ max = 3284, 1328, 1160, 1091, 815, 666 cm .
.6 Hz, 3 H) ppm. 13C NMR (75 MHz, CDCl
29.9, 126.9, 64.9, 59.1, 35.7, 35.3, 30.4, 21.9, 21.5, 13.8 ppm. Se
): δ = 331.9, 205.1 ppm. IR (neat): ν˜ max =
): δ = 143.8, 138.1,
HR-MS: calcd. for C18
354.1146.
H21NO
2
S [M + Na]+ 354.1140; found
3
7
7
NMR (76 MHz, CDCl
3
Compound 4h: R
f
= 0.70 (EtOAc/toluene, 3:7). Yield: 0.036 g, 15%.
H NMR (300 MHz, CDCl ): δ = 7.76 (d, J = 8.4 Hz, 2 H), 7.39–
.28 (m, 7 H), 5.43 (d, J = 9.9 Hz, 1 H), 4.92–4.86 (m, 1 H), 4.45
–1
3281, 1336, 1165, 1094, 817, 673 cm . HR-MS: calcd. for
1
+
3
C
14
H21NO
2
SSe
2
[M + Na] 449.9521; found 449.9549.
7
Compound 3f: R
f
= 0.65 (EtOAc/toluene, 3:7). Yield: 0.089 g, 64%.
(d, J = 3.0 Hz, 2 H), 4.04 (dt, J = 9.9, 3.3 Hz, 1 H), 3.89 (dd, J =
9.9, 6.9 Hz, 1 H), 3.61 (dd, J = 9.9, 7.8 Hz, 1 H), 3.23 (dd, J =
1
3
H NMR (300 MHz, CDCl ): δ = 7.75 (d, J = 8.4 Hz, 2 H), 7.31
(
(
d, J = 8.4 Hz, 2 H), 5.59–5.49 (m, 1 H), 5.34–5.25 (m, 1 H), 4.48 10.8, 3.3 Hz, 1 H), 2.89 (dd, J = 10.8, 3.2 Hz, 1 H), 2.42 (s, 3 H)
1
3
t, J = 6.0 Hz, 1 H), 3.54 (t, J = 6.0 Hz, 2 H), 2.43 (s, 3 H), 1.95–
3
ppm. C NMR (75 MHz, CDCl ): δ = 143.8, 137.9, 137.4, 129.9,
1
.89 (m, 2 H), 1.31–1.16 (m, 6 H), 0.66 (t, J = 7.5 Hz, 3 H) ppm. 128.5, 127.9, 127.7, 126.9, 73.5, 69.3, 60.9, 53.4, 35.9, 21.6 ppm.
13
77
C NMR (75 MHz, CDCl
3
): δ = 143.3, 137.1, 135.2, 129.6, 127.1,
3
Se NMR (76 MHz, CDCl ): δ = 287.0, 212.3 ppm. IR (neat): ν˜ max
–
1
124.2, 45.4, 32.0, 31.2, 28.5, 22.4, 21.5, 13.9 ppm. IR (neat): ν˜ max
= 3281, 1335, 1157, 1093, 812, 663 cm . HR-MS: calcd. for
–1
[M + Na]+ 513.9470; found 513.9486.
=
C
3279, 1326, 1159, 1094, 813, 665 cm . HR-MS: calcd. for
C
18
H21NO
2
SSe
2
+
15
H23NO
2
S [M + Na] 304.1347; found 304.1343.
= 0.70 (EtOAc/toluene, 3:7). Yield: 0.035 g, 16%.
H NMR (300 MHz, CDCl ): δ = 7.78 (d, J = 8.4 Hz, 2 H), 7.32
d, J = 8.4 Hz, 2 H), 5.21 (d, J = 9.9 Hz, 1 H), 4.75–4.69 (m, 1 H),
Compound 4i: R
f
= 0.70 (EtOAc/toluene, 3:7). Yield: 0.103 g, 50%;
1
Compound 4f: R
f
3
m.p. 128 °C. H NMR (300 MHz, CDCl ): δ = 7.79 (d, J = 8.1 Hz,
1
3
2 H), 7.32 (d, J = 8.1 Hz, 2 H), 5.23 (d, J = 10.2 Hz, 1 H), 4.82
(dd, J = 10.0, 2.4 Hz, 1 H), 3.87–3.81 (m, 1 H), 3.17 (dd, J = 10.0,
2.7 Hz, 1 H), 2.85 (dd, J = 11.1, 1.8 Hz, 1 H), 2.44 (s, 3 H), 1.83–
(
3
1
6
.51–3.45 (m, 1 H), 3.20 (dd, J = 10.8, 3.9 Hz, 1 H), 3.08 (dd, J =
0.8, 1.5 Hz, 1 H), 2.44 (s, 3 H), 1.54–1.35 (m, 2 H), 1.32–1.13 (m,
1.62 (m, 2 H), 1.33–1.21 (m, 2 H), 0.85 (t, J = 7.2 Hz, 3 H) ppm.
13
13
H), 0.86 (t, J = 6.6 Hz, 3 H) ppm. C NMR (75 MHz, CDCl
3
):
C NMR (75 MHz, CDCl
3
): δ = 143.7, 138.3, 129.8, 126.9, 62.1,
4
550 © 2007 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.eurjoc.org
Eur. J. Org. Chem. 2007, 4543–4551