10.1002/ejoc.202000791
European Journal of Organic Chemistry
FULL PAPER
7-chloro-4-phenylpyrrolo[1,2-a]quinoxaline (3g)
114.63. HRMS (ESI): m/z [M + H]+ calculated for C21H14N2: 295.1229;
found:295.1229
Yellow solid. (74%). mp 137-139 ℃. 1H NMR(500 MHz, CDCl3) δ 8.03 (d, J =
3,7-dimethyl-6-phenylindolo[1,2-a]quinoxaline (3n)
2.0 Hz, 1H), 7.98 (m, 2H), 7.94 (dd, J = 3.0, 1.5 Hz, 1H), 7.78 (d, J = 8.5 Hz,
1H), 7.54 (m, 3H), 7.45 (dd, J = 4.0, 2.5 Hz, 1H), 7.01 (dd, J = 4.0, 1.0 Hz, 1H).
13C NMR (125 MHz, CDCl3) δ 155.39, 138.03, 137.16, 130.38, 130.11, 129.53,
128.63, 127.43, 125.28, 125.24, 114.97, 114.76, 114.40, 109.39. HRMS (ESI):
m/z [M + H]+ calculated for C17H11CIN2: 279.0683; found: 279.0689.
Light yellow solid. (73%). mp 180-182 ℃. 1H NMR(500 MHz, CDCl3) δ 8.43 (d,
J = 8.5 Hz, 1H), 8.35 (d, J = 8.5 Hz, 1H), 7.87 (d, J = 8.5 Hz, 1H), 7.83 (s, 1H),
7.62 (m, 2H), 7.56 (m, 1H), 7.52 (m, 3H), 7.42 (t, J = 7.5 Hz, 1H), 7.38 (dd, J
= 8.5, 1.5 Hz, 1H), 2.48 (s, 3H), 2.05 (s, 3H). 13C NMR (125 MHz, CDCl3) δ
157.56, 133.49, 131.96, 130.22, 130.14, 129.19, 129.14, 128.62, 128.42,
128.31, 125.72, 124.60, 121.85, 120.72, 114.32, 114.14, 20.82, 11.11. HRMS
(ESI): m/z [M + H]+ calculated for C23H18N2: 323.1542; found: 323.1545.
8-chloro-4-phenylpyrrolo[1,2-a]quinoxaline (3h)
Light yellow solid. (77%). mp 175-177 ℃. 1H NMR(500 MHz, CDCl3) δ 7.98 (m,
3H), 7.92 (m, 1H), 7.86 (d, J = 2.0 Hz, 1H), 7.54 (m, 3H), 7.40 (dd, J = 4.0, 2.0
Hz, 1H), 7.02 (d, J = 4.0 Hz, 1H), 6.91 (m, 1H). 13C NMR (125 MHz, CDCl3) δ
154.48, 138.07, 134.78, 132.88, 131.35, 130.04, 128.64, 127.75, 125.73,
125.29, 114.93, 114.60, 113.80, 109.35. HRMS (ESI): m/z [M + H]+ calculated
for C17H11CIN2: 279.0683; found: 279.0682.
3-bromo-7-methyl-6-phenylindolo[1,2-a]quinoxaline (3o)
Yellow solid. (88%). mp 175-177 ℃. 1H NMR(400 MHz, CDCl3) δ 8.29 (d, J =
8.8 Hz, 1H), 8.22 (d, J = 8.8 Hz, 1H), 8.10 (d, J = 2.4 Hz, 1H), 7.85 (d, J = 4 Hz,
1H), 7.55 (m, 7H), 7.42 (m, 1H), 2.02 (s, 3H). 13C NMR (75 MHz, CDCl3) δ
158.72, 139.20, 137.00, 132.47, 131.96, 130.65, 130.30, 129.50, 129.48,
128.54, 128.49, 125.42, 125.17, 122.29, 120.96, 115.92, 115.52, 114.14,
111.78, 11.20. HRMS (ESI): m/z [M + H]+ calculated for C22H15BrN2: 387.0491;
found: 387.0494
7-bromo-4-phenylpyrrolo[1,2-a]quinoxaline (3i)
Yellow solid. (76%). mp 175-177 ℃. 1H NMR(500 MHz, CDCl3) δ 8.21 (s, 1H),
7.98 (dd, J = 7.0, 1.5 Hz, 2H), 7.96 (d, J = 1.5 Hz, 1H), 7.74 (d, J = 8.5 Hz, 1H),
7.60 (dd, J = 9.0, 2.5 Hz, 1H), 7.54 (m, 3H), 7.02 (d, J = 3.5 Hz, 1H), 6.91 (m,
1H). 13C NMR (125 MHz, CDCl3) δ 155.37, 138.03, 137.50, 132.66, 130.21,
130.14, 128.67, 128.64, 126.25, 125.32, 117.88, 115.06, 115.01, 114.47,
109.48. HRMS (ESI): m/z [M + H]+ calculated for C17H11BrN2: 323.0178; found:
323.0178.
2-methoxy-7-methyl-6-phenylindolo[1,2-a]quinoxaline (3p)
Yellow solid. (83%). mp 171-173 ℃. 1H NMR(500 MHz, CDCl3) δ 8.39 (d, J =
8.5 Hz, 1H), 7.93 (m, 2H), 7.85 (d, J = 8.0 Hz, 1H), 7.61 (m, 2H), 7.53 (m, 4H),
7.43 (t, J = 7.5 Hz, 1H), 6.95 (dd, J = 8.5, 2.5 Hz, 1H), 3.99 (s, 3H), 2.03 (s,
3H). 13C NMR (125 MHz, CDCl3) δ 159.67, 154.85, 139.70, 131.84, 131.34,
131.05, 130.47, 130.15, 129.03, 128.67, 128.40, 125.65, 124.38, 122.05,
120.58, 114.21, 110.35, 109.31, 100.21, 55.80, 11.09. HRMS (ESI): m/z [M +
H]+ calculated for C23H18N2O: 339.1491; found: 339.1490.
7,8-dimethyl-4-phenylpyrrolo[1,2-a]quinoxaline (3j)
Yellow solid. (79%). mp 104-106 ℃. 1H NMR(300 MHz, CDCl3) δ 7.98 (m, 2H),
7.90 (dd, J = 2.7, 1.2 Hz, 1 H), 7.80 (s, 1H), 7.60 (s, 1H), 7.50 (m, 3H), 6.93
(dd, J = 4.2, 1.2 Hz, 1H), 6.83 (dd, J = 4.2, 2.7 Hz, 1H), 2.43 (s, 3H), 2.38 (s,
3H). 13C NMR (75 MHz, CDCl3) δ 153.36, 138.71, 136.97, 134.49, 134.09,
130.31, 129.57, 128.63, 128.57, 125.38, 125.11, 114.09, 113.60, 108.10,
20.27, 19.56. HRMS (ESI): m/z [M + H]+ calculated for C19H16N2: 273.1385;
found: 273.1381.
6-phenylpyrido[3,2-e]pyrrolo[1,2-a]pyrazine (3q)
Yellow solid. (76%). mp 136-138 ℃. 1H NMR(400 MHz, CDCl3) δ 8.52 (d, J =
4.0 Hz, 1H), 8.47 (s, 1H), 8.30 (d, J = 4.0 Hz, 1H), 8.00 (m, 2H), 7.54 (m, 3H),
7.43 (dd, J = 8.0, 4.4 Hz, 1H), 7.05 (d, J = 4.0 Hz, 1H), 6.92 (t, J = 3.2 Hz, 1H).
13C NMR (75 MHz, CDCl3) δ 155.26, 146.64, 139.35, 138.01, 137.34, 131.72,
130.15, 128.66, 126.84, 121.63, 116.05, 114.49, 110.38. HRMS (ESI): m/z [M
+ H]+ calculated for C16H11N3: 246.1025; found: 246.1030.
7,8-difluoro-4-phenylpyrrolo[1,2-a]quinoxaline (3k)
Light yellow solid. (85%). mp 102-104 ℃. 1H NMR(500 MHz, CDCl3) δ 7.97 (m,
2H), 7.84 (m, 2H), 7.65 (dd, J = 10.5, 7.0 Hz, 1H), 7.55 (m, 3H), 7.02 (dd, J =
4.0, 0.5 Hz, 1H), 6.92 (dd, J = 4.0, 3.0 Hz, 1H). 13C NMR (125 MHz, CDCl3) δ
154.79, 154.77, (J = 2.5 Hz), 150.60, 150.48, (J = 15 Hz), 149.10, 148.99, (J =
13.75 Hz), 148.60, 148.49, (J = 13.75 Hz), 147.14, 147.03, (J = 13.75 Hz),
137.88, 130.14, 128.68, 128.57, (J = 13.75 Hz), 124.94, 123.60, 123.58, (J =
2.5 Hz), 123.53, 123.51, (J = 2.5 Hz), 117.67, 117.53, (J = 17.5 Hz), 114.98,
114.16, 109.39, 102.33, 102.15, (J = 22.5 Hz). HRMS (ESI): m/z [M + H]+
calculated for C17H10N2F2: 281.0884; found: 281.0887.
4-(p-tolyl)pyrrolo[1,2-a]quinoxaline (4a)
Brown solid. (76%). mp 61-63 ℃. 1H NMR(500 MHz, CDCl3) δ 8.02 (dd, J =
8.0, 1.5 Hz, 1H), 7.93 (dd, J = 2.5, 1.0 Hz, 1H), 7.90 (m, 2H), 7.81 (dd, J = 8.0,
1.0 Hz, 1H), 7.43 (m, 2H), 7.33 (d, J = 8.0 Hz, 1H), 6.97 (dd, J = 4.0, 1.5 Hz,
1H), 6.85 (dd, J = 3.5, 2.5 Hz, 1H), 2.44 (s, 3H). 13C NMR (125 MHz, CDCl3) δ
154.29, 139.87, 136.24, 135.62, 130.09, 129.23, 128.54, 127.24, 127.07,
125.36, 114.50, 113.86, 113.55, 108.67, 21.45. HRMS (ESI): m/z [M + H]+
calculated for C18H14N2: 259.1229; found: 259.1230.
7,8-dichloro-4-phenylpyrrolo[1,2-a]quinoxaline (3l)
4-(m-tolyl)pyrrolo[1,2-a]quinoxaline (4b)
Yellow solid. (74%). mp 156-158 ℃. 1H NMR(500 MHz, CDCl3) δ 8.12(s, 1H),
7.96(dd, J = 7.5, 2.5 Hz, 1H), 7.93(s, 1H), 7.89(dd, J = 2.5, 0.5 Hz, 1H), 7.55(d,
J = 2.5 Hz, 1H), 7.04(dd, J = 4.0, 0.5 Hz, 1H), 6.91(dd, J = 4.0, 3.0Hz, 1H). 13
NMR (125 MHz, CDCl3) δ 155.41, 137.49, 135.37, 131.01, 130.86, 130.39,
128.98, 128.70, 128.64, 126.23, 125.05, 115.50, 115.27, 115.00, 110.29.
HRMS (ESI): m/z [M + H]+ calculated for C17H10CI2N2: 295.1229; found:
312.0293
C
Light yellow solid. (82%). mp 53-55 ℃. 1H NMR(500 MHz, CDCl3) δ 8.03 (d, J
= 8.0 Hz, 1H), 7.93 (d, J = 1.0 Hz, 1H), 7.79 (m, 3H), 7.43 (m, 3H), 7.32 (d, J =
7.5 Hz, 1H), 6.97 (d, J = 3.0 Hz, 1H), 6.85 (m, 1H), 2.46 (s, 3H). 13C NMR (125
MHz, CDCl3) δ 154.55, 130.55, 130.16, 129.17, 128.35, 127.34, 125.72,
125.20, 114.52, 113.88, 113.57, 108.74, 21.53. HRMS (ESI): m/z [M + H]+
calculated for C18H14N2: 259.1229; found: 259.1231.
6-phenylindolo[1,2-a]quinoxaline (3m)
4-(4-(tert-butyl)phenyl)pyrrolo[1,2-a]quinoxaline (4c)
Yellow solid. (43%). mp 156-158 ℃. 1H NMR(500 MHz, CDCl3) δ 8.53 (m, 2H),
8.12 (d, J = 5.0 Hz, 1H), 8.03 (m, 2H), 7.94 (d, J = 8.0 Hz, 1H), 7.63 (td, J =
10.0, 1.5. Hz, 1H), 7.58 (m, 4H), 7.46 (m, 2H), 7.27 (s, 1H). 13C NMR (125
MHz, CDCl3) δ 156.26, 133.16, 130.48, 130.46, 130.23, 130.15, 130.13,
129.26, 128.69, 128.44, 124.53, 124.50, 124.27, 122.86, 122.74, 114.69,
Yellow solid. (67%). mp 112-114 ℃. 1H NMR(500 MHz, CDCl3) δ 8.04 (m, 1H),
7.97 (dd, J = 2.5, 1.0 Hz, 1H), 7.94 (m, 2H), 7.85 (dd, J = 4.0, 1.0 Hz, 1H),
7.56 (dt, J = 3.5, 1.5Hz, 1H), 7.49 (td, J = 7.5, 1.5Hz, 1H), 7.43 (td, J = 8.0,
1.5Hz, 1H), 7.03 (dd, J = 4.0, 1.0 Hz, 1H), 6.88 (dd, J = 4.0, 3.0 Hz, 1H), 1.39
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