X. Xiong et al.
(
s, 2H), 2.46 (s, 2H), 2.30 (s, 2H), 1.13 (d, J = 7.8 Hz,
Ethyl 4-(4-chlorophenyl)-1,4,5,6,7,8-hexahydro-2,7,7-
3
H), 1.10 (s, 3H). ESI–MS calcd m/z 284.1, ꢀound 285.1
trimethyl-5-oxoquinoline-3-carboxylate (13): m.p.
+
−1
[
(M + 1)] .
231–232 °C. FT-IR (KBr disc) cm : 3275, 3207, 3076,
2
,7,7-Trimethyl-5-oxo-4-phenyl-1,4,5,6,7,8-hexahydro-
2960, 1705, 1645, 1602, 1489, 1381, 1280, 1215, 1107,
1
quinoline-3-carboxylic acid ethyl ester (8): m.p. 208–209 °C.
1080. H NMR (400 MHz, CDCl ) δ: 7.26 (d, J=8.5 Hz,
3
−
1
FT-IR (KBr disc) cm : 3292, 3220, 3080, 2962, 2930,
2H), 7.18 (d, J=8.4 Hz, 2H), 5.99 (s, 1H), 5.05 (s, 1H), 4.08
(q, J=7.1 Hz, 2H), 2.44–2.32 (m, 4H), 2.29–2.14 (m, 3H),
1.21 (t, J=7.1 Hz, 3H), 1.10 (s, 3H), 0.95 (s, 3H). ESI–MS
1
1
2
700, 1643, 1610, 1483, 1381, 1309, 1278, 1210, 1109,
1
070. H NMR (400 MHz, CDCl ) δ: 7.32 (d, J=7.3 Hz,
3
+
H), 7.21 (t, J=7.5 Hz, 2H), 7.11 (t, J=7.3 Hz, 1H), 5.83
calcd m/z 373.1, ꢀound 374.1 [(M+1)] .
(
s, 1H), 5.08 (s, 1H), 4.13–4.01 (m, 2H), 3.75 (q, J=7.0 Hz,
Ethyl 4-(ꢀuran-2-yl)-1,4,5,6,7,8-hexahydro-2,7,7-trime-
2
3
H), 2.40 (s, 2H), 1.31–1.24 (m, 3H), 1.21 (t, J = 7.1 Hz,
thyl-5-oxoquinoline-3-carboxylate (14): m.p. 247–248 °C.
−1
H), 1.10 (s, 3H), 0.96 (s, 3H). ESI–MS calcd m/z 339.1,
FT-IR (KBr disc) cm : 3288, 3221, 3084, 2966, 2935, 2877,
+
ꢀ
ound 340.1 [(M+1)] .
1678, 1608, 1491, 1396, 1377, 1320, 1220, 1180, 1145,
1
Ethyl 1,4,5,6,7,8-hexahydro-4-(4-methoxyphenyl)-2,7,7-
1105, 1074, 1010, 927, 796. H NMR (400 MHz, CDCl ) δ:
3
trimethyl-5-oxoquinoline-3-carboxylate (9): m.p.
6.95 (s, 1H), 6.74 (dd, J =17.4, 8.2 Hz, 2H), 5.82 (s, 1H),
5.00 (s, 1H), 4.10 (q, J=7.1 Hz, 2H), 2.38 (d, J=22.2 Hz,
4H), 2.24 (q, J=16.5 Hz, 3H), 1.24 (t, J=6.1 Hz, 3H), 1.11
(s, 3H), 0.98 (s, 3H). ESI–MS calcd m/z 329.1, ꢀound 330.1
−
1
2
3
1
57–258 °C. FT-IR (KBr disc) cm : 3277, 3244, 3207,
078, 2963, 2936, 1705, 1647, 1604, 1491, 1381, 1309, 1280,
1
215, 1190, 1167, 1153, 1107, 1072. H NMR (400 MHz,
+
CDCl ) δ: 7.23 (t, J=5.8 Hz, 2H), 6.75 (t, J=5.8 Hz, 2H),
[(M+1)] .
3
6
.06 (s, 1H), 5.02 (s, 1H), 4.08 (q, J=7.1 Hz, 2H), 3.74 (d,
Acknowledgements This work was ꢀinancially supported by the
National Natural Science Foundation oꢀ China (21004024), the Natu-
ral Science Foundation oꢀ Fujian province (2016J01063), the Program
J = 7.9 Hz, 3H), 2.39 (s, 3H), 2.30–2.12 (m, 3H), 1.22 (t,
J=7.1 Hz, 3H), 1.09 (s, 3H), 0.96 (s, 3H). ESI–MS calcd
+
m/z 369.2, ꢀound 370.2 [(M+1)] .
ꢀ
or New Century Excellent Talents in University oꢀ Fujian province
Ethyl 1,4,5,6,7,8-hexahydro-4-(4-hydroxyphenyl)-2,7,7-
(2012FJ-NCET-ZR03) and the Promotion Program ꢀor Young and
Middle-aged Teacher in Science and Technology Research oꢀ Huaqiao
University (ZQN-YX103).
trimethyl-5-oxoquinoline-3-carboxylate (10): m.p.
−
1
2
3
1
45–246 °C. FT-IR (KBr disc) cm : 3146, 3282, 3209,
078, 2958, 1685, 1650, 1615, 1508, 1485, 1381, 1307,
1
284, 1220, 1168, 1138, 1120. H NMR (400 MHz,
References
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3
5
2
1
3
.96–5.86 (m, 1H), 5.00 (s, 1H), 4.08 (q, J =7.1 Hz, 2H),
.41 (s, 3H), 2.33–2.14 (m, 4H), 1.22 (t, J = 7.1 Hz, 3H),
.10 (s, 3H), 0.96 (s, 3H). ESI–MS calcd m/z 355.1, ꢀound
1
.
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3
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.
.
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ylate (11): m.p. 210–212 °C. FT-IR (KBr disc) cm : 3398,
3
1
298, 3072, 2955, 1700, 1643, 1591, 1510, 1485, 1381,
1
3
:1375
310, 1273, 1215, 1168, 1128, 1070. H NMR (400 MHz,
5
.
Kemnitzer W, Drewe J, Jiang S, Zhang H, Wang Y, Zhao J, Jia S,
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3
5
3
3
.86–5.72 (m, 1H), 5.00 (s, 1H), 4.10 (q, J =6.8 Hz, 2H),
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6
.
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+
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ꢀound 386.2 [(M+1)] .
Ethyl 1,4,5,6,7,8-hexahydro-2,7,7-trimethyl-4-(4-
8
.
Valente S, Mellini P, Spallotta F, Caraꢀa V, Nebbioso A, Polletta
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nitrophenyl)-5-oxoquinoline-3-carboxylate (12): m.p.
−
1
2
3
1
40–241 °C. FT-IR (KBr disc) cm : 3443, 3275, 3192,
074, 2966, 1703, 1650, 1606, 1518, 1492, 1381, 1345,
(
2016) J Med Chem 59:1471
1
307, 1280, 1215, 1189, 1150, 1109, 1070. H NMR
9
.
Moghaddas M, Davoodnia A (2015) Res Chem Intermed 41:4373
(
400 MHz, CDCl ) δ: 8.10 (d, J = 7.9 Hz, 2H), 7.52 (t,
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3
1
1
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J = 10.0 Hz, 2H), 5.90 (s, 1H), 5.18 (s, 1H), 4.07 (q,
J = 7.0 Hz, 2H), 2.45 (s, 3H), 2.22 (dd, J = 37.9, 15.9 Hz,
4
H), 1.19 (t, J = 7.1 Hz, 3H), 1.12 (s, 3H), 0.94 (s, 3H).
1
3. Sharma P, Gupta M (2015) Green Chem 17:1100
+
ESI–MS calcd m/z 384.1, ꢀound 385.1 [(M+1)] .
14. Khurana JM, Nand B, Saluja P (2010) Tetrahedron 66:5637
1
3