The Journal of Organic Chemistry
Article
6-(4-Fluorophenyl)indolo[1,2-c]quinazoline (4f).7c Petroleum
ether/ethyl acetate (30:1) as eluent; yellow solid (79 mg, 63%), mp
217−219 °C. 1H NMR (CDCl3, 400 MHz) δ 6.54 (d, J = 8.8 Hz, 1H),
7.05 (t, J = 8.0 Hz, 1H), 7.23 (s, 1H), 7.29−7.35 (m, 3H), 7.47−7.56
(m, 2H), 7.65−7.68 (m, 2H), 7.77 (d, J = 7.6 Hz, 1H), 7.84 (d, J = 8.0
Hz, 1H), 8.06 (d, J = 7.6 Hz, 1H); 13C NMR (CDCl3, 100 MHz) δ
96.0, 114.8, 116.5 (d, J = 22.1 Hz, 2C), 120.5, 120.7, 121.6, 122.8,
123.6, 127.6, 127.8, 129.2, 130.5, 130.6 (d, J = 8.4 Hz, 2C), 131.6,
132.1 (d, J = 3.8 Hz, 1C), 135.2, 139.0, 148.4, 163.9 (d, J = 249.2 Hz,
1C). MS (ESI) m/z 313 [M + H]+.
6-(4-Bromophenyl)indolo[1,2-c]quinazoline (4g). Petroleum
ether/ethyl acetate (40:1) as eluent; yellow solid (47 mg, 31%), mp
204−206 °C. 1H NMR (CDCl3, 400 MHz) δ 6.61 (d, J = 8.8 Hz, 1H),
7.06 (t, J = 8.0 Hz, 1H), 7.26 (s, 1H), 7.34 (t, J = 8.0 Hz, 1H), 7.49−
7.58 (m, 4H), 7.75−7.83 (m, 4H), 8.09 (d, J = 7.2 Hz, 1H); 13C NMR
(CDCl3, 100 MHz) δ 96.0, 114.7, 120.6, 120.7, 121.7, 122.8, 123.7,
124.9, 127.7, 127.9, 129.2, 130.1, 130.4, 131.4, 132.5, 134.8, 135.2,
139.0, 148.2. HRMS (ESI) calcd for C21H14BrN2 [M + H]+ 373.0335,
found 373.0364.
1H), 7.41−7.56 (m, 6H), 7.68−7.74 (m, 3H), 7.83 (d, J = 8.0 Hz,
1H), 7.88 (d, J = 8.4 Hz, 1H), 7.97 (d, J = 16.0 Hz, 1H), 8.05 (t, J =
8.4 Hz, 2H); 13C NMR (CDCl3, 100 MHz) δ 95.6, 115.0, 120.3, 120.9,
121.2, 122.2, 122.7, 123.6, 127.1, 127.4, 127.8, 129.06, 129.13, 129.7,
130.6, 131.6, 135.1, 135.6, 138.9, 139.8, 147.7. MS (ESI) m/z 321 [M
+ H]+.
6-Propylindolo[1,2-c]quinazoline (4n).7b Petroleum ether/ethyl
acetate (20:1) as eluent; yellow solid (36 mg, 35%), mp 95−97 °C. 1H
NMR (CDCl3, 400 MHz) δ 1.23 (t, J = 7.6 Hz, 3H), 2.04−2.11 (m,
2H), 3.40 (t, J = 7.6 Hz, 2H), 7.23 (s, 1H), 7.38−7.48 (m, 3H), 7.53
(t, J = 7.6 Hz, 1H), 7.77 (d, J = 7.6 Hz, 1H), 7.84 (d, J = 7.2 Hz, 1H),
7.99 (d, J = 7.6 Hz, 1H), 8.05 (d, J = 8.0 Hz, 1H); 13C NMR (CDCl3,
100 MHz) δ 13.8, 19.6, 38.6, 95.6, 115.0, 120.3, 120.8, 122.2, 122.6,
123.3, 126.8, 127.0, 129.0, 130.6, 131.2, 135.2, 138.6, 151.6. MS (ESI)
m/z 261 [M + H]+.
Indolo[1,2-c]quinazoline (4o).7b Petroleum ether/ethyl acetate
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(10:1) as eluent; yellow solid (26 mg, 30%), mp 199−200 °C. H
NMR (CDCl3, 400 MHz) δ 7.14 (s, 1H), 7.40−7.47 (m, 2H), 7.50−
7.58 (m, 2H), 7.82−7.84 (m, 2H), 7.96 (d, J = 8.0 Hz, 1H), 8.06 (d, J
= 8.0 Hz, 1H), 9.06 (s, 1H); 13C NMR (CDCl3, 100 MHz) δ 94.9,
109.9, 121.0, 121.3, 122.4, 123.2, 124.2, 127.8, 128.0, 129.2, 129.8,
130.4, 132.8, 137.2, 139.1. MS (ESI) m/z 219 [M + H]+.
6-(4-Chlorophenyl)indolo[1,2-c]quinazoline (4h).7b Petroleum
ether/ethyl acetate (40:1) as eluent; yellow solid (79 mg, 60%), mp
201−203 °C. 1H NMR (CDCl3, 400 MHz) δ 6.60 (d, J = 8.0 Hz, 1H),
7.06 (t, J = 8.0 Hz, 1H), 7.23 (s, 1H), 7.34 (t, J = 7.6 Hz, 1H), 7.47−
7.56 (m, 2H), 7.58−7.63 (m, 4H), 7.77 (d, J = 7.6 Hz, 1H), 7.83 (d, J
= 7.6 Hz, 1H), 8.06 (d, J = 7.2 Hz, 1H); 13C NMR (CDCl3, 100 MHz)
δ 96.0, 114.8, 120.5, 120.7, 121.7, 122.8, 123.7, 127.6, 127.9, 129.2,
129.6, 129.9, 130.4, 131.4, 134.3, 135.2, 136.6, 139.0, 148.2. MS (ESI)
m/z 329 [M + H]+.
6-(3-Chlorophenyl)indolo[1,2-c]quinazoline (4i). Petroleum
ether/ethyl acetate (40:1) as eluent; yellow solid (73 mg, 55%), mp
167−169 °C. 1H NMR (CDCl3, 400 MHz) δ 6.56 (d, J = 8.8 Hz, 1H),
7.05 (t, J = 8.0 Hz, 1H), 7.25 (s, 1H), 7.34 (t, J = 7.6 Hz, 1H), 7.49−
7.56 (m, 4H), 7.65 (s, 1H), 7.71 (s, 1H), 7.78 (d, J = 8.0 Hz, 1H), 7.84
(d, J = 7.2 Hz, 1H), 8.09 (d, J = 7.6 Hz, 1H); 13C NMR (CDCl3, 100
MHz) δ 96.1, 114.7, 120.6, 120.7, 121.8, 122.8, 123.7, 126.6, 127.7,
127.9, 128.6, 129.2, 130.4, 130.6, 130.7, 131.4, 135.1, 135.4, 137.4,
138.9, 147.8. HRMS (ESI) calcd for C21H14ClN2 [M + H]+ 329.0840,
found 329.0862.
6-(2-Chlorophenyl)indolo[1,2-c]quinazoline (4j). Petroleum
ether/ethyl acetate (15:1) as eluent; yellow solid (82 mg, 62%), mp
119−121 °C. 1H NMR (CDCl3, 400 MHz) δ 6.37 (d, J = 8.0 Hz, 1H),
7.05 (t, J = 8.0 Hz, 1H), 7.31 (s, 1H), 7.35 (t, J = 8.0 Hz, 1H), 7.52−
7.66 (m, 6H), 7.80 (d, J = 8.0 Hz, 1H), 7.90 (d, J = 7.6 Hz, 1H), 8.14
(d, J = 7.6 Hz, 1H); 13C NMR (CDCl3, 100 MHz) δ 96.0, 113.4,
120.7, 120.8, 122.3, 122.9, 123.7, 127.8, 128.0, 129.2, 130.31, 130.32,
130.4, 131.3, 131.7, 133.4, 134.7, 135.2, 139.0, 146.7 (one 13C signal
was not observed). HRMS (ESI) calcd for C21H14ClN2 [M + H]+
329.0840, found 329.0862.
10-Chloro-6-phenylindolo[1,2-c]quinazoline (4p).7b Petroleum
ether/ethyl acetate (15:1) as eluent; yellow solid (79 mg, 60%), mp
205−207 °C. 1H NMR (CDCl3, 400 MHz) δ 6.34 (d, J = 8.8 Hz, 1H),
6.92 (d, J = 8.8 Hz, 1H), 7.19 (s, 1H), 7.51−7.58 (m, 2H), 7.60−7.65
(m, 5H), 7.71 (s, 1H), 7.86 (d, J = 8.0 Hz, 1H), 8.09 (d, J = 8.0 Hz,
1H); 13C NMR (CDCl3, 100 MHz) δ 95.2, 115.9, 119.7, 120.2, 121.8,
122.9, 127.7, 127.9, 128.2, 129.3, 129.5, 129.6, 130.0, 130.7, 131.5,
135.4, 136.5, 139.1, 149.0. MS (ESI) m/z 329 [M + H]+.
10-Chloro-6-p-tolylindolo[1,2-c]quinazoline (4q). Petroleum
ether/ethyl acetate (15:1) as eluent; yellow solid (87 mg, 64%), mp
212−214 °C. 1H NMR (CDCl3, 400 MHz) δ 2.53 (s, 3H), 6.45 (d, J =
9.2 Hz, 1H), 6.94 (d, J = 9.2 Hz, 1H), 7.15 (s, 1H), 7.42 (d, J = 7.2 Hz,
2H), 7.48−7.57 (m, 4H), 7.69 (s, 1H), 7.85 (d, J = 7.6 Hz, 1H), 8.06
(d, J = 7.2 Hz, 1H); 13C NMR (CDCl3, 100 MHz) δ 21.7, 95.1, 116.0,
119.6, 120.1, 121.7, 122.8, 127.5, 127.9, 128.1, 129.2, 129.5, 130.0,
131.5, 132.6, 136.5, 139.3, 140.8, 149.1 (one 13C signal was not
observed). HRMS (ESI) calcd for C22H16ClN2 [M + H]+ 343.0997,
found 343.1018.
10-Chloro-6-(4-chlorophenyl)indolo[1,2-c]quinazoline (4r).7b Pe-
troleum ether/ethyl acetate (15:1) as eluent; yellow solid (110 mg,
1
76%), mp 244−246 °C. H NMR (CDCl3, 400 MHz) δ 6.49 (d, J =
9.2 Hz, 1H), 6.99 (d, J = 9.6 Hz, 1H), 7.20 (s, 1H), 7.51−7.62 (m,
6H), 7.73 (s, 1H), 7.83 (d, J = 8.0 Hz, 1H), 8.09 (d, J = 7.2 Hz, 1H);
13C NMR (CDCl3, 100 MHz) δ 95.4, 115.6, 119.9, 120.2, 121.9, 122.9,
127.9, 128.0, 129.5, 129.67, 129.73, 129.78, 129.82, 131.5, 133.8,
136.5, 136.9, 139.0, 147.8. MS (ESI) m/z 364 [M + H]+.
10-Chloro-6-(thiophen-2-yl)indolo[1,2-c]quinazoline (4s).7b Pe-
troleum ether/ethyl acetate (15:1) as eluent; yellow solid (104 mg,
6-(Naphthalen-1-yl)indolo[1,2-c]quinazoline (4k). Petroleum
ether/ethyl acetate (20:1) as eluent; yellow solid (83 mg, 60%), mp
148−150 °C. 1H NMR (CDCl3, 400 MHz) δ 5.99 (d, J = 8.8 Hz, 1H),
6.79 (t, J = 8.0 Hz, 1H), 7.25 (t, J = 8.0 Hz, 1H), 7.33−7.37 (m, 2H),
7.51−7.64 (m, 4H), 7.71−7.80 (m, 3H), 7.95−7.97 (m, 1H), 8.02 (d, J
= 8.4 Hz, 1H), 8.16−8.22 (m, 2H); 13C NMR (CDCl3, 100 MHz) δ
96.0, 114.6, 120.5, 120.8, 121.9, 122.9, 123.5, 124.7, 125.9, 126.7,
126.9, 127.6, 127.7, 128.1, 128.6, 129.2, 130.4, 130.6, 131.0, 131.3,
133.4, 133.8, 135.0, 139.3, 148.5. HRMS (ESI) calcd for C25H17N2 [M
+ H]+ 345.1386, found 345.1389.
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78%), mp 234−236 °C. H NMR (DMSO-d6, 400 MHz) δ 6.59 (d, J
= 9.2 Hz, 1H), 7.12 (dd, J = 1.6, 9.2 Hz, 1H), 7.35 (t, J = 4.0 Hz, 1H),
7.55 (s, 1H), 7.58−7.63 (m, 3H), 7.75 (d, J = 7.2 Hz, 1H), 7.87 (s,
1H), 7.98 (d, J = 4.8 Hz, 1H), 8.13 (d, J = 8.0 Hz, 1H); 13C NMR
(DMSO-d6, 100 MHz) δ 96.3, 116.1, 120.1, 120.3, 121.9, 123.9, 128.0,
128.2, 128.6, 128.7, 130.0, 130.3, 130.4, 131.6, 135.3, 136.7, 139.1,
143.3 (one 13C signal was not observed). MS (ESI) m/z 335 [M +
H]+.
6-(Thiophen-2-yl)indolo[1,2-c]quinazoline (4l).7b Petroleum
ether/ethyl acetate (15:1) as eluent; yellow solid (64 mg, 53%), mp
10-Chloro-6-propylindolo[1,2-c]quinazoline (4t). Petroleum
ether/ethyl acetate (20:1) as eluent; yellow solid (53 mg, 45%), mp
124−126 °C. 1H NMR (CDCl3, 400 MHz) δ 1.21 (t, J = 7.6 Hz, 3H),
2.00−2.10 (m, 2H), 3.30 (t, J = 7.6 Hz, 2H), 7.10 (s, 1H), 7.31 (d, J =
9.6 Hz, 1H), 7.46 (t, J = 7.6 Hz, 1H), 7.54 (t, J = 8.0 Hz, 1H), 7.75 (m,
2H), 7.86 (d, J = 9.6 Hz, 1H), 8.01 (d, J = 8.0 Hz, 1H); 13C NMR
(CDCl3, 100 MHz) δ 13.9, 19.4, 38.6, 94.8, 115.9, 119.9, 120.0, 122.2,
122.7, 127.0, 127.3, 129.0, 129.3, 129.5, 131.6, 136.5, 138.9, 150.8.
HRMS (ESI) calcd for C18H16ClN2 [M + H]+ 295.0997, found
295.1025.
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163−164 °C. H NMR (CDCl3, 400 MHz) δ 6.72−6.74 (m, 1H),
7.07−7.11 (m, 1H), 7.26−7.29 (m, 2H), 7.33−7.37 (m, 1H), 7.49−
7.57 (m, 3H), 7.65−7.66 (m, 1H), 7.79 (d, J = 8.0 Hz, 1H), 7.83−7.86
(m, 1H), 8.09−8.11 (m, 1H); 13C NMR (CDCl3, 100 MHz) δ 96.0,
114.8, 120.6, 120.7, 121.7, 122.7, 123.6, 127.5, 127.8, 128.0, 128.3,
129.1, 129.2, 130.4, 131.6, 135.3, 136.0, 139.0, 143.5. MS (ESI) m/z
301 [M + H]+.
(E)-6-Styrylindolo[1,2-c]quinazoline (4m).16a Petroleum ether/
ethyl acetate (40:1) as eluent; yellow solid (72 mg, 56%), mp 182−
2-Methoxy-6-phenylindolo[1,2-c]quinazoline (4u). Petroleum
ether/ethyl acetate (15:1) as eluent; yellow solid (91 mg, 70%), mp
1
184 °C. H NMR (CDCl3, 400 MHz) δ 7.21 (s, 1H), 7.34−7.38 (m,
G
J. Org. Chem. XXXX, XXX, XXX−XXX