Y. Fu, J.-Y. Wang, W.-G. Chen, Y. Li, L.-X. Zhao, S. Gao, and F. Ye
Vol 000
7
(
2
.33 (s, 4H, Ar-H), 5.13–5.14 (m, 2H, 2 × CO-CH), 4.92–4.97
d, J = 14.4 Hz, 2H, 2 × COCHO), 4.47–4.51 (d, J = 14.4 Hz,
H, 2 × N-CH), 2.12 (s, 6H, 2 × O═C-CH ), 1.01–1.03 (d,
Calcd. for C H Cl N O: 320.0250. Found: 343.0143
13 15 3 2
[M + Na] .
+
N-trichloroacetyl-2,3,7-trimethyl-1,2,3,4-tetrahydroquinoxaline
3
13
(4m). White solid. Yield 80%. mp 160–161°C. IR (KBr,
J = 6.3 Hz, 6H, 2 × CH ). C NMR (150 MHz, CDCl , ppm):
3
3
ꢀ
1
cm ) v: 3344 (N–H), 2996–2864 (C–H), 1655 (C═O),
δ: 170.54, 170.39, 165.74, 165.43, 133.44, 133.44, 127.53,
27.53, 124.57, 123.41, 61.66, 61.66, 49.31, 49.31, 20.44,
0.44, 15.19, 9.81; HRMS m/z. Calcd. for C H N O :
1
1
617–1447 (C═C). H NMR (300 MHz, DMSO-d6,
ppm): δ: 8.31 (s, 1H, Ar-H), 6.17 (s, 2H, Ar-H), 5.08 (s,
1H, N–H), 2.72 (s, 2H, 2 × N-CH), 2.03 (s, 3H, Ar-CH ),
1
2
18 22 2 6
+
3
62.1477. Found: 363.1555 [M + H] .
3
13
0
N,N -bis(phenoxyacetyl)-2,3-dimethyl-1,2,3,4-tetrahydroquinoxaline
4i).
1.01–1.03 (d, J = 5.7 Hz, 6H, 2 × CH ). C NMR
3
(
White solid. Yield 75%. mp 161–162°C. IR (KBr,
(75 MHz, DMSO-d , ppm): δ: 160.47, 137.47, 136.14,
6
ꢀ
1
cm ) v: 3060–2857 (C–H), 1688 (C═O), 1598–1445
127.88, 125.70, 116.36, 114.82, 94.22, 52.49, 50.44,
1
(C═C). H NMR (600 MHz, DMSO-d , ppm): δ: 6.75–7.61
22.22, 21.29, 17.39; HRMS m/z. Calcd. for
6
+
(m, 14H, Ar-H), 5.02–5.04 (d, J = 14.4 Hz, 4H, 2 × Ar-O-
C H Cl N O: 320.0250. Found: 343.0143 [M + Na] .
13
15
0
3 2
N,N -bis(acetoxyacetyl)-2,3,6-trimethyl-1,2,3,4-tetrahydro-
CH ), 4.67–4.70 (d, J = 15.0 Hz, 2H, 2 × N-CH), 0.96–
2
13
quinoxaline (4n).
cm ) v: 2960–2854 (C–H), 1748 (C═O), 1680 (C═O),
Yellow liquid. Yield 59%. IR (KBr,
0.97 (d, J = 6.0 Hz, 6H, 2 × CH3). C NMR (150 MHz,
ꢀ
1
DMSO-d , ppm): δ: 165.81, 165.81, 157.68, 157.68,
6
1
1
7
2
614–1434 (C═C). H NMR (300 MHz, CDCl , ppm): δ:
.09–7.71 (m, 3H, Ar-H), 4.76–5.10 (m, 4H,
1
1
32.74, 132.74, 129.35, 129.35, 129.35, 129.35, 127.04,
27.04, 125.87, 125.87, 120.94, 120.94, 114.33, 114.33,
3
× COCH O), 4.09–4.51 (m, 2H, 2 × N-CH), 2.31–2.38
114.33, 114.33, 65.77, 65.77, 52.96, 52.96, 15.09, 15.09;
2
(
d, J = 19.2 Hz, 3H, Ar-CH ), 2.02–2.14 (m, 6H,
HRMS m/z. Calcd. for C H N O : 430.1892. Found:
3
26 26 2 4
+
2 × COCH ), 1.16–1.26 (m, 3H, CH ), 0.98–1.00 (d,
3 3
431.1966 [M + H] .
13
J = 5.7 Hz, 3H, CH3). C NMR (75 MHz, CDCl , ppm):
N-chloroacetyl-2,3,6-trimethyl-1,2,3,4-tetrahydroquinoxaline
3
ꢀ
1
(
4j). White oil. Yield 70%. IR (KBr, cm ) v: 3311 (N–H),
δ: 170.62, 170.62, 165.47, 165.47, 138.01, 133.17, 130.64,
128.23, 126.65, 125.87, 62.27, 61.54, 53.58, 53.58, 29.73,
21.25, 20.55, 15.24, 15.20; HRMS m/z. Calcd. for
1
2
973–2873 (C–H), 1663 (C═O), 1613–1447 (C═C). H
NMR (300 MHz, CDCl , ppm): δ: 7.01–7.50 (m, 3H,
Ar-H), 5.14 (s, 1H, N–H), 4.28–4.29 (m, 2H, 2 × N-CH),
4
3
+
C H N O : 376.1634. Found: 377.1711 [M + H] .
19
24
0
2
6
N,N -bis(phenoxyacetyl)-2,3,6-trimethyl-1,2,3,4-tetrahydro-
.12–4.14 (d, J = 6.3 Hz, 2H, 2 × CH-Cl ), 2.47 (s, 3H,
2
1
3
quinoxaline (4o).
White solid. Yield 63%. mp
Ar-CH ), 1.01–1.20 (m, 6H, 2 × CH ). C NMR
3
3
ꢀ
1
1
36–137°C. IR (KBr, cm ) v: 3064–2862 (C–H), 1667
(75 MHz, CDCl , ppm): δ: 165.03, 138.29, 133.70,
3
1
(C═O), 1589–1449 (C═C).
H NMR (600 MHz,
1
2
31.22, 128.57, 126.34, 124.00, 54.11, 42.09, 41.29,
1.13, 17.61, 15.23. HRMS m/z. Calcd. for
DMSO-d , ppm): δ: 6.90–7.81 (m, 13H, Ar-H), 5.01–5.11
6
+
(m, 4H, 2 × Ar-O-CH ), 4.35–4.36 (d, J = 4.8 Hz, 2H,
2
C H ClN O: 252.1029. Found: 252.0310 [M + H] .
13
17
0
2
N,N -bis(dichloroacetyl)-2,3,6-trimethyl-1,2,3,4-tetrahydro-
2 × N-CH) 2.22 (s, 3H, Ar-CH ), 1.11–1.12 (d, J = 6.6 Hz,
3
13
quinoxaline (4k). White solid. Yield 69%. mp 127–128°C.
IR (KBr, cm ) v: 3036–2871 (C–H), 1683 (C═O), 1586–
6H, 2 × CH3). C NMR (150 MHz, DMSO-d , ppm): δ:
6
ꢀ
1
167.64, 167.45, 157.72, 157.71, 132.99, 129.48, 129.48,
129.48, 129.48, 125.38, 124.56, 123.68, 123.36, 123.12,
121.10, 121.10, 114.51, 114.51, 114.50, 114.50, 66.82,
66.82, 50.77, 50.77, 20.57, 16.63, 16.59; HRMS m/z.
Calcd. for C H N O : 310.1681. Found: 333.1571
1
1
7
2
2
2
1
6
462 (C═C). H NMR (300 MHz, CDCl , ppm): δ: 7.23–
.33 (m, 3H, Ar-H), 6.33–6.35 (d, J = 7.2 Hz, 2H,
3
× CH-Cl ), 5.19–5.20 (d, J = 2.4 Hz, 2H, 2 × N-CH),
2
.47 (s, 3H, Ar-CH ), 1.04–1.06 (d, J = 5.7 Hz, 6H,
3
27 28 2 4
13
+
× CH3). C NMR (75 MHz, CDCl , ppm): δ: 162.51,
[M + Na] .
3
0
62.48, 139.68, 133.15, 130.61, 129.63, 126.44, 125.67,
3.99, 63.96, 54.95, 54.95, 21.41, 15.04, 15.00; HRMS
N,N -bis(dichloroacetyl)-2,3-dimethyl-6-methoxyl-1,2,3,4-
tetrahydroquinoxaline (4p). White solid. Yield 70%. mp
ꢀ
1
1
(
31–132°C. IR (KBr, cm ) v: 3017–2853 (C–H), 1697
m/z. Calcd. for C H Cl N O : 395.9965. Found:
15
16
4 2 2
1
+
C═O), 1597–1462 (C═C). H NMR (300 MHz, CDCl ,
3
97.0042 [M + H] .
3
N-trichloroacetyl-2,3,6-trimethyl-1,2,3,4-tetrahydroquinoxaline
4l). Yellow solid. Yield 72%. mp 138–139°C. IR (KBr,
ppm): δ: 6.95–7.34 (m, 3H, Ar-H), 6.31, 6.37 (s, 2H,
(
2 × CHCl ), 5.18–5.21 (t, J = 5.4 Hz, 2H, 2 × N-CH), 3.89
2
ꢀ
1
cm ) v: 3324 (N–H), 2980–2852 (C–H), 1664 (C═O),
1
(s, 3H, Ar-CH ), 1.04–1.09 (dd, J = 6.3 Hz, J = 9.0 Hz,
3
1
2
1
13
620–1446 (C═C). H NMR (300 MHz, DMSO-d , ppm):
6H, 2 × CH3). C NMR (75 MHz, CDCl , ppm): δ:
6
3
δ: 6.39–7.11 (m, 3H, Ar-H), 6.30–6.33 (d, J = 8.4 Hz, 1H,
N–H), 4.48–4.50 (d, J = 6.0 Hz, 1H, N-CH), 3.43–3.46 (t,
J = 4.8 Hz, 1H, N-CH), 2.13–2.15 (d, J = 6.3 Hz, 3H,
Ar-CH ), 1.06–1.13 (dd, J = 6.3 Hz, J = 14.1 Hz, 6H,
162.52, 162.52, 159.74, 134.42, 126.80, 126.65, 113.78,
111.89, 63.92, 63.92, 55.99, 55.99, 54.74, 15.05, 15.05;
HRMS m/z. Calcd. for C H Cl N O : 411.9915. Found:
15
16
4 2 3
+
3
1
2
412.9990 [M + H] .
13
2
1
9
× CH3). C NMR (75 MHz, DMSO-d , ppm): δ:
60.47, 137.47, 136.14, 127.88, 125.70, 116.36, 114.82,
4.22, 52.49, 50.44, 22.22, 21.29, 17.39; HRMS m/z.
N-dichloroacetyl-3-phenyl-1,2-dihydro-2H-quinoxaline (6).
6
ꢀ
1
Yellow solid. Yield 49%. mp 151–152°C. IR (KBr, cm
)
v: 3065–3027 (C–H), 1676 (C═O), 1606–1445 (C═C),
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet