Organic & Biomolecular Chemistry
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ARTICLE
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1218, 1106; HRMS (ES TOF) calc`d for C21H14FN2 (M+H)+ 313.1136, MHz, CDCl3) δ 9.83 (br s, 1H), 8.30 (d, J = 8.1 Hz, 1H), 8.V2ie0w(dArdti,clJe=On8l.in1e,
found 313.1143 (2.2 ppm).
0.9 Hz, 1H), 7.88 (dd, J = 7.8, 1.6 Hz, 2H), 7.D6O7I(:d10d.d10, 3J9=/C88.4O,B70.005,818.4E
Hz, 1H), 7.60−7.49 (m, 5H), 7.36 (d, J = 0.7 Hz, 1H), 7.24 (dd, J = 8.3,
1.2 Hz, 1H), 2.37 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 156.6, 145.4,
141.4, 140.8, 137.2, 130.4, 129.8, 129.2, 129.1 (2C), 128.6 (2C),
128.6, 127.1, 125.7, 123.1, 122.0, 120.9, 116.4, 113.2, 111.1, 21.8;
FTIR (KBr, cm-1) 2931, 2366, 1642, 1563, 1442, 1336, 1225, 1119;
HRMS (TOF-ES) calcd for C22H17N2 (M+H)+ 309.1386, found 309.1391
(1.5 ppm).
6-(2-Chlorophenyl)-11H-indolo[3,2-c]quinoline (1af): This comp-
ound was prepared according to the Typical Procedure B employing
2-(1-(2-phenylhydrazineylidene)ethyl)aniline (12a) (225 mg, 1.00
mmol) and 1-chloro-2-(2-nitrovinyl)benzene (5f) (202 mg, 1.10
mmol). Yield 158 mg (0.48 mmol, 48%), colorless crystals, m.p.
234.7-237.2oC (EtOH), Rf 0.55 (petroleum ether/ EtOAc 1:1); 1H NMR
(400 MHz, DMSO) δ 12.93 (s, 1H), 8.60 (d, J = 7.8 Hz, 1H), 8.14 (d, J =
8.1 Hz, 1H), 7.85 – 7.69 (m, 4H), 7.69 – 7.56 (m, 3H), 7.43 (t, J = 7.6 5-Methyl-6-phenyl-5H-indolo[3,2-c]quinoline (1ca):6 This comp-
Hz, 1H), 7.10 (t, J = 7.6 Hz, 1H), 6.89 (d, J = 7.9 Hz, 1H); 13C NMR (101 ound was prepared according to the Typical Procedure C employing
MHz, DMSO) δ 153.0, 144.9, 140.3, 139.4, 139.0, 131.9, 130.7, 130.5, phenylhydrazine (2a) (108 mg, 1.00 mmol), o-(N-methylamino)-
129.5(2C), 128.5, 127.7, 126.0, 125.5, 122.1, 121.6, 120.6, 120.1, acetophenone (3b) (149 mg, 1.00 mmol), and b-nitrostyrene (5a)
116.6, 112.9, 112.0; FTIR (KBr, cm-1): 3067, 2703, 1707, 1695, 1661, (164 mg, 1.10 mmol). Yield 228 mg (0.74 mmol, 74%), yellow
1561, 1507, 1452, 1440, 1365, 1231; HRMS (ES TOF) calc`d for crystals, mp 258-262 oC (benzene), Rf 0.27 (EtOAc/EtOH 2:1); 1H NMR
C21H14Cl1N2 (M+H)+ 329.0840, found 329.0847 (2.2 ppm).
(400 MHz, CDCl3) δ 8.76 (d, J = 7.9 Hz, 1H), 8.09 (d, J = 8.9 Hz, 1H),
7.96 (d, J = 8.2 Hz, 1H), 7.85− 7.79 (m, 3H), 7.76−7.71 (m, 2H), 7.63−
7.57 (m, 1H), 7.48−7.42 (m, 1H), 7.35−7.29 (m, 1H), 7.09−7.04 (m,
1H), 6.41 (d, J = 8.1 Hz, 1H), 4.32 (s, 3H); 13C NMR (101 MHz, CDCl3)
δ 152.4, 145.4, 136.8, 132.4, 132.0, 131.4, 130.2 (2C), 130.1, 128.5
(2C), 128.3, 127.7, 127.3, 125.2, 122.8, 122.7, 120.7, 118.2, 115.5,
114.9, 54.8; FTIR (KBr, cm-1) 3441, 3054, 2975, 1540, 1447, 1349,
1261, 1060, 1011; HRMS (TOF-ES) calcd for C22H17N2 (M+H)+
309.1386, found 309.1385 (0.4 ppm).
6-(2-Methoxyphenyl)-11H-indolo[3,2-c]quinoline (1ag): This comp-
ound was prepared according to the Typical Procedure B employing
2-(1-(2-phenylhydrazineylidene)ethyl)aniline (12a) (225 mg, 1.00
mmol) and 1-methoxy-2-(2-nitrovinyl)benzene (5g) (197 mg, 1.10
mmol). Yield 168.5 mg (0.52 mmol, 52%), colorless crystals, m.p.
o
266.0-268.1 C (EtOH), Rf 0.33 (EtOAc/hexane 1:1); 1H NMR (400
MHz, DMSO) δ 12.78 (s, 1H), 8.56 (d, J = 7.9 Hz, 1H), 8.10 (d, J = 8.1
Hz, 1H), 7.75 (dd, J = 14.4, 6.9 Hz, 1H), 7.69 (dd, J = 7.4, 3.8 Hz, 2H),
7.60 (td, J = 8.2, 1.2 Hz, 1H), 7.41 (dd, J = 14.3, 7.1 Hz, 2H), 7.28 (d, J 5,8-Dimethyl-6-phenyl-5H-indolo[3,2-c]quinoline (1da):6
This
= 8.3 Hz, 1H), 7.18 (t, J = 7.4 Hz, 1H), 7.08 (t, J = 7.5 Hz, 1H), 7.02 (d, J compound was prepared according to the Typical Procedure C
= 7.8 Hz, 1H), 3.59 (s, 3H); 13C NMR (101 MHz, DMSO) δ 156.9, 153.4, employing p-tolylhydrazine (2b) (122 mg, 1.00 mmol), o-(N-methyl-
145.1, 140.0, 138.8, 130.2, 130.1, 129.8, 129.4, 128.2, 125.6, 125.2, amino)acetophenone (3b) (149 mg, 1.00 mmol), and b-nitrostyrene
122.1, 122.0, 120.7, 120.4, 120.3, 116.5, 113.6, 111.8, 111.3, 55.3; (5a) (164 mg, 1.10 mmol). Yield 242 mg (0.75 mmol, 75%), yellow
FTIR (KBr, cm-1): 3063, 2929, 1590 ,1561, 1519, 1503, 1457, 1440, crystals, mp 234-236 oC (benzene), Rf = 0.15 (petroleum ether/ EtOAc
1348, 1302, 1244, 1152; HRMS (ES TOF) calc`d for C22H17N2O (M+H)+ 1:1); 1H NMR (400 MHz, CDCl3) δ 9.04 (dd, J = 8.0, 1.0 Hz, 1H), 7.85
325.1335, found 325.1343 (2.4 ppm).
(d, J = 8.2 Hz, 1H), 7.78 (d, J = 8.4 Hz, 1H), 7.75−7.59 (m, 5H), 7.48 (dd,
J = 7.7, 1.6 Hz, 2H), 7.24 (dd, J = 8.1, 1.2 Hz, 1H), 6.26 (s, 1H), 3.84 (s,
3H), 2.26 (s, 3H); 13C NMR (101 MHz, CDCl3) δ 153.1, 147.7, 136.5,
134.0, 130.1, 129.6, 129.6 (2C), 129.3, 128.6 (2C), 128.3, 127.5,
126.4, 125.2, 125.0, 121.6, 120.4, 118.5, 117.2, 116.5, 37.1, 21.7;
FTIR (KBr, cm-1) 2931, 2366, 1659, 1439, 1339, 1260, 1032; HRMS
(TOF-ES) calcd for C23H19N2 (M + H)+ 323.1543, found 323.1550 (2.2
ppm).
6-Hexyl-11H-indolo[3,2-c]quinoline (1ah): This compound was
prepared according to the Typical Procedure B employing 2-(1-(2-
phenylhydrazineylidene)ethyl)aniline (12a) (225 mg, 1.00 mmol) and
1-nitrooct-1-ene (5h) (173 mg, 1.10 mmol). Yield 193 mg (0.64 mmol,
64%), light-yellow crystals, m.p. 176-178 oC (EtOH), Rf 0.21
(EtOAc/hexane); 1H NMR (400 MHz, DMSO) δ 12.73 (s, 1H), 8.49 (d, J
= 8.0 Hz, 1H), 8.13 (d, J = 8.0 Hz, 1H), 8.05 (d, J = 8.3 Hz, 1H), 7.71 (dd,
J = 17.9, 8.1 Hz, 2H), 7.62 (t, J = 7.5 Hz, 1H), 7.49 (t, J = 7.6 Hz, 1H), 8-Isopropyl-6-phenyl-11H-indolo[3,2-c]quinoline (1ea): This comp-
7.37 (t, J = 7.5 Hz, 1H), 3.40 (t, J = 7.8 Hz, 2H), 1.95 – 1.83 (m, 2H), ound was prepared according to the Typical Procedure B employing
1.52 (dt, J = 14.9, 7.2 Hz, 2H), 1.41 – 1.23 (m, 4H), 0.86 (t, J = 6.9 Hz, 2-(1-(2-(4-isopropylphenyl)hydrazineylidene)ethyl)aniline (12e) (267
3H); 13C NMR (101 MHz, DMSO) δ 158.2, 144.9, 140.3, 138.8, 128.9, mg, 1.00 mmol) and b-nitrostyrene (5a) (164 mg, 1.10 mmol). Yield
o
128.1, 125.0, 124.9, 121.8, 121.8, 121.4, 120.8, 116.3, 112.4, 111.9, 279 mg (0.83 mmol, 83%), colorless crystals, m.p. 129.0-132.6 C
1
37.3, 31.3, 28.9, 27.9, 22.1, 14.0; FTIR (KBr, cm-1): 2925, 2364, 1561, (EtOH), Rf 0.71 (EtOAc/hexane 1:1); H NMR (400 MHz, DMSO) δ
1511, 1457, 1361, 1252; HRMS (ES TOF) calc`d for C21H23N2 (M+H)+ 12.77 (s, 1H), 8.55 (d, J = 8.0 Hz, 1H), 8.12 (d, J = 8.2 Hz, 1H), 7.87 –
303.1856, found 303.1867 (3.9 ppm).
7.79 (m, 2H), 7.75 (t, J = 7.2 Hz, 1H), 7.71 – 7.67 (m, 1H), 7.66 – 7.60
(m, 4H), 7.34 (d, J = 8.7 Hz, 2H), 2.87 (hept, J = 6.9 Hz, 1H), 1.14 (d, J
= 6.9Hz, 6H); 13C NMR (101 MHz, DMSO) δ 155.5, 144.9, 141.1, 140.7,
140.2, 137.6, 129.4, 129.0 (2C), 128.9, 128.4, 128.3 (2C), 125.6,
124.6, 121.9, 121.7, 118.0, 116.4, 112.0, 111.6, 33.4, 24.4 (2C); FTIR
(KBr, cm-1): 3056, 2920, 2366, 1615, 1590, 1557, 1516, 1490, 1443;
HRMS (ES TOF) calc`d for C24H21N2 (M+H)+ 337.1699, found 337.1703
(1.2 ppm).
8-Methyl-6-phenyl-11H-indolo[3,2-c]quinoline (1ba):6 This comp-
ound was prepared according to the Typical Procedure C employing
p-tolylhydrazine (2b) (122 mg, 1.00 mmol), o-aminoacetophenone
(3a) (135 mg, 1.00 mmol), and b-nitrostyrene (5a) (164 mg, 1.10
mmol). Yield 237 mg (0.77 mmol, 77%), colorless crystals, mp 231-
o
1
233 C (EtOH); Rf 0.56 (petroleum ether/EtOAc 1:1); H NMR (400
6 | J. Name., 2012, 00, 1-3
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