The Journal of Organic Chemistry
Page 12 of 16
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(cm ) 2919, 2840, 1657, 1576, 1511, 1450, 1144, 870, 824,
1H), 8.54 (dd, J = 4.8, 1.2 Hz, 1H), 7.57−7.50 (m, 1H),
+
+
737. HRMS(ESI): calculated for C15
258.0947, found: 258.0946.
H16NOS [M+H] m/z:
7.35−7.20 (m, 2H), 6.21−6.17 (dd, J = 8.8, 0.8 Hz, 1H),
6.17−6.13 (dd, J = 7.2, 1.2 Hz, 1H), 3.47 (d, J = 11.6 Hz,
1H), 3.43 (d, J = 11.6 Hz, 1H), 2.24 (s, 3H). 13C{ H} NMR
1
(
±)-3,4-Dihydro-2H,2'H,5'H-spiro[naphthalene-1,3'-thia-
zolo[3,2-a]pyridin]-5'-one (8n) was synthesized according
to General Procedure B from 1-methylene-1,2,3,4-tetrahy-
dronaphthalene (116 mg, 2.0 eq, 0.8 mmol), to give 72 mg
3
(100 MHz, CDCl ) δ 162.1, 148.8, 148.1, 146.4, 140.0,
137.9, 132.5, 123.3, 116.9, 100.5, 73.1, 44.0, 22.8. IR (KBr)
-
1
ν (cm ) 3038, 2977, 2936, 1654, 1577, 1508, 1419, 1400,
product 8n as colorless oil liquid in 67% yield; R
f
= 0.35 (2:1
petroleum ether/ethyl acetate). H NMR (400 MHz, CDCl
δ 7.20 (dd, J = 8.8, 7.2 Hz, 1H), 7.16−7.11 (m, 3H),
1376, 1278, 1227, 1147, 1103, 1021, 780, 711. HRMS(ESI):
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
+
+
3
)
calculated for C13
245.0745.
13 2
H N OS [M+H] m/z: 245.0743, found:
7
1
2
1
.06−7.00 (m, 1H), 6.16− 6.07 (m, 2H), 3.58 (dd, J = 12.0,
.6 Hz, 1H), 3.45 (d, J = 12.0 Hz, 1H), 3.13−2.98 (m, 1H),
.88−2.74 (m, 1H), 2.59 (t, J = 12.8 Hz, 1H), 2.35 (d, J =
(±)-3-Methyl-3-(thiophen-3-yl)-2,3-dihydro-5H-thia-
zolo[3,2-a]pyridin-5-one (8r) was synthesized according to
General Procedure B from 3-(prop-1-en-2-yl)thiophene (50
mg, 1.0 eq, 0.4 mmol), to give 54 mg product 8r as yellow
13
1
2.8 Hz, 1H), 2.15−2.00 (m, 1H), 1.89−1.70 (m, 1H). C{ H}
) δ 161.4, 148.2, 139.3, 138.5, 137.1,
128.9, 127.1, 126.7, 125.1, 117.0, 99.9, 74.3, 42.0, 29.3, 28.7,
NMR (100 MHz, CDCl
3
oil liquid in 54% yield; R
acetate). H NMR (400 MHz, CDCl ) δ 7.27 (dd, J = 4.8, 2.8
f
= 0.30 (2:1 petroleum ether/ethyl
1
3
-
1
21.3. IR (KBr) ν (cm ) 3019, 2927, 2863, 1651, 1574, 1513,
1446, 1400, 1351, 1220, 1124, 1144, 1109, 1040, 1025, 966,
37, 764, 742. HRMS(ESI): calculated for C16H16NOS
M+H] m/z: 270.0947, found: 270.0945.
±)-3-Methyl-3-(naphthalen-1-yl)-2,3-dihydro-5H-thia-
zolo[3,2-a]pyridin-5-one (8o) was synthesized according to
General Procedure B from 1-(prop-1-en-2-yl) naphthalene
134 mg, 2.0 eq, 0.8 mmol), to give 62 mg product 8o as
colorless oil liquid in 53% yield; R = 0.33 (2:1 petroleum
ether/ethyl acetate). H NMR (400 MHz, CDCl ) δ 7.88 (d,
J = 7.6 Hz, 1H), 7.83 (d, J = 8.0 Hz, 1H), 7.76 (d, J = 7.6 Hz,
H), 7.51 (t, J = 7.6 Hz, 1H), 7.47−7.20 (m, 3H), 7.20 (dd, J
7.2, 6.8 Hz, 1H), 6.23 (dd, J = 7.2, 0.8 Hz, 1H), 5.96 (d, J
= 9.2, 1H), 4.11 (d, J = 11.6 Hz, 1H), 3.20 (d, J = 11.2 Hz,
1H), 2.31 (s, 3H). C{ H} NMR (100 MHz, CDCl
147.3, 139.7, 137.2, 134.9, 130.2, 129.6, 126.4, 125.2(d),
125.1, 122.8, 116.5, 100.5, 74.8, 41.3, 23.4. IR (KBr) ν (cm
) 3084, 3050, 2978, 2876, 1654, 1577, 1508, 1458, 1400,
Hz, 1H), 7.20 (dd, J = 8.8, 6.8 Hz, 1H), 7.14 (dd, J = 2.8, 1.2
Hz, 1H), 6.99 (dd, J = 5.2, 1.2 Hz, 1H), 6.16 (d, J = 8.8 Hz,
1H), 6.09 (d, J = 7.2 Hz, 1H), 3.46 (d, J = 11.6 Hz, 1H), 3.39
+
8
[
+
13
1
(d, J = 11.6 Hz, 1H), 2.21 (s, 3H). C{ H} NMR (100 MHz,
CDCl ) δ 162.4, 148.1, 143.4, 139.6, 126.3, 125.1, 120.8,
(
3
-
1
116.9, 100.2, 72.4, 43.2, 24.0. IR (KBr) ν (cm ) 3088, 3046,
2975, 2933, 1654, 1578, 1511, 1440, 1400, 1375, 1267, 1146,
1114, 1029, 777, 737, 663. HRMS(ESI): calculated for
(
+
+
f
12
C H
12NOS
2
[M+H] m/z: 250.0355, found: 250.0357.
1
3
(±)-trans-2,3-Diphenyl-2,3-dihydro-5H-thiazolo[3,2-
a]pyridin-5-one (8s) was synthesized according to General
Procedure B from trans-1,2-diphenylethene (144 mg, 2.0 eq,
0.8 mmol), to give 83 mg product 8s as colorless oil liquid
1
=
in 68% yield; R
f
= 0.36 (2:1 petroleum ether/ethyl acetate).
H NMR (400 MHz, CDCl ) δ 7.45−7.21 (m, 11H), 6.29 (d,
J = 9.2 Hz, 1H), 6.24 (s, 1 H), 6.23 (d, 1H, overlap), 4.60 (s,
1
3
1
1
3
) δ 161.6,
3
-
13
1
1H). C{ H} NMR (100 MHz, CDCl
3
) δ 161.7, 148.0, 141.2,
1
1
40.4, 138.1, 129.3, 128.9, 128.6, 128.5, 126.3, 125.6, 115.6,
-
1
1375, 1261, 1198, 1177, 1141, 1092, 1032, 794, 742.
99.9, 72.7, 56.2. IR (KBr) ν (cm ) 3060, 3031, 2958, 1653,
16NOS+ [M+H] m/z:
+
HRMS(ESI): calculated for C18
94.0947, found: 294.0944.
±)-3-((Benzyloxy)methyl)-3-phenyl-2,3-dihydro-5H-thi-
azolo[3,2-a]pyridin-5-one (8p) was synthesized according
to General Procedure B from (3-(benzyloxy)prop-1-en-2-
yl)benzene (180 mg, 2.0 eq, 0.8 mmol), to give 36 mg prod-
H
1576, 1511, 1452, 1406, 1266, 1220, 1141, 1078, 1031, 779,
+
2
734, 696. HRMS(ESI): calculated for C19
[M+Na] m/z: 328.0767, found: 328.0769.
H15NNaOS
+
(
(±)-Ethyl3-(3,3-dimethyl-5-oxo-2,3-dihydro-5H-thia-
zolo[3,2-a]pyridin-2-yl)propanoate (8t) was synthesized ac-
cording to General Procedure B from ethyl 5-methylhex-4-
enoate (62 mg, 1.0 eq, 0.4 mmol), to give 76 mg product 8t
uct 8p as colorless oil liquid in 26% yield; R
f
= 0.40 (2:1
petroleum ether/ethyl acetate). H NMR (400 MHz, CDCl
δ 7.38−7.15 (m, 10H), 6.20 (dd, J = 9.2, 0.8 Hz, 1H), 6.12
dd, J = 7.2, 1.2 Hz, 1H), 4.67 (d, J = 12.0 Hz, 1H), 4.65 (d,
J = 9.6 Hz, 1H), 4.62 (d, J = 12.0 Hz, 1H), 4.11 (d, J = 11.2
1
)
as colorless oil liquid in 68% yield; R
f
ether/ethyl acetate). H NMR (400 MHz, CDCl ) δ 7.12 (dd,
= 0.30 (2:1 petroleum
3
1
3
(
J = 9.2, 7.2 Hz, 1H), 6.18 (d, J = 8.8 Hz, 1H), 6.00 (dd, J =
7.2, 0.8 Hz, 1H), 4.17 (q, J = 7.2, 2H), 3.57 (dd, J = 12.0, 2.8
Hz, 1H), 2.55−2.45 (m, 1H), 2.44− 2.30 (m, 1H), 2.29−2.10
1
3
1
Hz), 3.30 (d, J = 11.2 Hz, 1H). C{ H} NMR (100 MHz,
CDCl ) δ 162.8, 149.8, 139.9, 139.6, 137.9, 128.6, 128.4,
128.0, 127.7, 125.0, 116.4, 100.3, 77.8, 73.4, 72.3, 39.7. IR
KBr) ν (cm ) 3029, 2865, 1651, 1574, 1504, 1402, 1265,
147, 1027, 850, 696. HRMS(ESI): calculated for
(m, 1H), 1.86 (s, 3H), 1.90−1.78 (m, 1H), 1.55 (s, 3H), 1.27
3
(t, J = 7.2 Hz, 3H). 13C{ H} NMR (100 MHz, CDCl
1
) δ
3
-
1
(
172.0, 163.1, 146.5, 138.9, 117.2, 100.5, 72.7, 60.9, 55.5,
-1
1
C
32.9, 25.3, 24.4, 17.8, 14.2. IR (KBr) ν (cm ) 2977, 2933,
+
+
H
20NO
2
S [M+H] m/z: 350.1209, found: 350.1206.
1733, 1655, 1579, 1517, 1442, 1385, 1247, 1181, 1091, 1038,
21
+
+
(
±)-3-Methyl-3-(pyridin-3-yl)-2,3-dihydro-5H-thia-
778. HRMS(ESI): calculated for C14
282.1158, found: 282.1161.
3
H20NO S [M+H] m/z:
zolo[3,2-a]pyridin-5-one (8q) was synthesized according to
General Procedure B from 3-(prop-1-en-2-yl)pyridine (48
mg, 1.0 eq, 0.4 mmol), to give 21 mg product 8q as yellow
oil liquid in 21% yield; R
acetate). H NMR (400 MHz, CDCl ) δ 8.60 (d, J = 2.0 Hz,
(±)-9A-methyl-5a,6,7,8,9,9a-hexahydro-1H-
benzo[4,5]thiazolo[3,2-a]pyridin-1-one (8u) was synthe-
sized according to General Procedure B from 1-methylcy-
clohex-1-ene (126 mg, 2.0 eq, 0.8 mmol), to give (44 mg
f
= 0.10 (2:1 petroleum ether/ethyl
1
3
12
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