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129.1, 128.8, 128.1, 126.4, 123.6, 123.0, 121.7, 120.7, 120.2,
117.0, 109.3, 32.1 ppm. HRMS (ESI): calcd for C22H15NO:
310.1226 [M + H+]; found 310.1227.
3-Chloro-5-phenyl-benzo[a]uoren-11-one (2q)
Red-orange solid. Yield: 74% (63 mg). Mp: 215–217 ꢀC. 1H NMR
(400 MHz, CDCl3): d 9.00 (d, J ¼ 9.2 Hz, 1H), 7.76 (d, J ¼ 9.2 Hz,
1H), 7.62 (d, J ¼ 6.8 Hz, 2H), 7.58–7.53 (m, 3H), 7.52–7.48 (m,
3H), 7.46–7.42 (m, 2H), 7.31–7.27 (m, 1H) ppm. 13C NMR (100
MHz, CDCl3): d 194.8, 147.5, 145.5, 143.4, 139.5, 134.6, 134.4,
133.4, 132.7, 130.0, 129.6, 129.0, 128.7, 128.4, 126.1, 126.0,
125.8, 124.0, 120.5, 120.1 ppm. HRMS (ESI): calcd for
5-Thiophen-2-yl-benzo[a]uoren-11-one (2k)
Yellow solid. Yield: 60% (47 mg). Mp: 233–235 ꢀC. 1H NMR (400
MHz, CDCl3): d 8.19 (s, 1H), 7.66 (d, J ¼ 6.8 Hz, 1H), 7.60–7.55
(m, 3H), 7.52 (d, J ¼ 5.6 Hz, 1H), 7.74–7.45 (m, 2H), 7.20–7.13
(m, 2H), 6.98 (d, J ¼ 5.6 Hz, 1H), 6.49 (d, J ¼ 7.2 Hz, 1H) ppm.
13C NMR (100 MHz, CDCl3): d 193.2, 144.9, 144.8, 139.8, 137.7,
136.4, 135.8, 134.5, 132.9, 131.9, 130.6, 129.3, 129.1, 128.43,
128.38, 124.3, 124.1, 123.1, 118.8 ppm. HRMS (ESI): calcd for
C
23H13ClO: 341.0728 [M + H+]; found 341.0695.
8-Bromo-5-phenyl-benzo[a]uoren-11-one (2r)
Orange solid. Yield: 70% (67 mg). Mp: 237–239 ꢀC. 1H NMR (400
MHz, CDCl3): d 9.04 (d, J ¼ 8.4 Hz, 1H), 7.82 (d, J ¼ 8.8 Hz, 1H),
7.63–7.59 (m, 2H), 7.57 (s, 1H), 7.57–7.47 (m, 6H), 7.44–7.38 (m,
2H) ppm. 13C NMR (100 MHz, CDCl3): d 193.8, 148.7, 145.5,
144.1, 139.9, 133.5, 132.9, 132.1, 130.7, 129.7, 129.4, 129.0,
128.5, 128.3, 127.0, 126.8, 126.3, 125.0, 124.6, 123.5, 119.4 ppm.
HRMS (ESI): calcd for C23H13BrO: 385.0223 [M + H+]; found
385.0220.
C
21H12SO: 313.0682 [M + H+]; found 313.0708.
Benzo[a]uoren-11-one (2l)3b
Red-orange solid. Yield: 55% (32 mg). Mp: 132–134 ꢀC [Lit. 132
ꢀC]. 1H NMR (400 MHz, CDCl3): d 8.95 (d, J ¼ 8.4 Hz, 1H), 7.98
(d, J ¼ 8.4 Hz, 1H), 7.78 (d, J ¼ 8.4 Hz, 1H), 7.64 (d, J ¼ 8.0 Hz,
1H), 7.61–7.56 (m, 2H), 7.49–7.41 (m, 3H), 7.28–7.24 (m,
1H) ppm. 13C NMR (100 MHz, CDCl3): d 195.4, 146.1, 143.9,
135.9, 134.6, 134.4, 134.2, 130.2, 129.4, 129.3, 128.5, 126.9,
126.4, 124.3, 123.8, 119.9, 118.1 ppm.
8,10-Dibromo-5-phenyl-benzo[a]uoren-11-one (2s)
Orange solid. Yield: 61% (70 mg). Mp: 269–271 ꢀC. 1H NMR (400
MHz, CDCl3): d 9.02 (d, J ¼ 8.4 Hz, 1H), 7.81 (d, J ¼ 8.4 Hz, 1H),
7.61–7.59 (m, 1H), 7.57–7.54 (m, 2H), 7.52–7.50 (m, 2H), 7.51–
7.49 (m, 1H), 7.47–7.45 (m, 1H), 7.42–7.39 (m, 2H), 7.40–7.36
(m, 1H) ppm. 13C NMR (100 MHz, CDCl3): d 193.5, 148.3, 145.1,
143.6, 139.5, 133.1, 132.5, 131.7, 130.3, 129.3, 129.0, 128.7,
128.6, 128.3, 128.1, 127.9, 126.6, 126.4, 125.9, 124.6, 124.2,
123.1, 119.0 ppm. MS (ESI): m/z 485 [M + Na+]. Anal. calcd for
4-Methyl-5-phenyl-benzo[a]uoren-11-one (2m)
Red-orange solid. Yield: 60% (48 mg). Mp: 255–257 ꢀC. 1H NMR
(400 MHz, CDCl3): d 8.96 (d, J ¼ 7.6 Hz, 1H), 8.0 (d, J ¼ 8.0 Hz,
1H), 7.79 (d, J ¼ 8.4 Hz, 1H), 7.66 (d, J ¼ 8.4 Hz, 1H), 7.62–7.57
(m, 2H), 7.50 (d, J ¼ 7.6 Hz, 2H), 7.46–7.42 (m, 3H), 7.29–7.25
(m, 1H), 7.17 (d, J ¼ 7.2 Hz, 1H), 2.33 (s, 3H), ppm. 13C NMR (100
MHz, CDCl3): d 195.3, 148.7, 145.7, 143.8, 138.2, 137.4, 135.0,
134.3, 132.8, 131.0, 129.8, 129.4, 129.34, 129.29, 127.2, 126.5,
126.0, 124.7, 123.9, 120.0, 119.5 ppm. HRMS (ESI): calcd for
C
23H12Br2O: C 59.52, H 2.61; found: C 59.63, H 2.55.
3-Phenyl-1-(2-phenylacetyl-phenyl)propenone (7)10
24H16O: 321.1274 [M + H+]; found 321.1308.
Compound 7 was obtained by heating under reux 1a (0.25
mmol) with silver(I) triate (10 mg, 15 mol%) in the presence of
water (0.25 mL) in acetonitrile (5 mL). Pale yellow solid. Yield:
68% (56 mg). Mp: 90–92 ꢀC [Lit. 91.8–93.6 ꢀC]. 1H NMR (400
MHz, CDCl3): d 8.01–7.99 (m, 2H), 7.72 (dd, J ¼ 7.6 Hz, 1.2 Hz,
1H), 7.57–7.35 (m, 10H), 7.30 (d, J ¼ 7.6 Hz, 1H), 7.24 (s, 1H),
7.20 (s, 1H), 4.62 (s, 2H) ppm. 13C NMR (100 MHz, CDCl3):
d 197.3, 195.1, 145.9, 138.7, 137.0, 134.7, 134.7, 133.1, 132.5,
131.2, 130.6, 129.1, 128.9, 128.6, 128.5, 128.3, 126.9, 125.6,
43.6 ppm. Compound 7 when heated under reux with iodine in
AcOH afforded benzo[a]uorenone 2a in 85% yield.
C
3-Methyl-5-phenyl-benzo[a]uoren-11-one (2n)
Red-orange solid. Yield: 73% (58 mg). Mp: 219–221 ꢀC. 1H NMR
(400 MHz, CDCl3): d 8.96 (d, J ¼ 8.4 Hz, 1H), 7.61 (d, J ¼ 7.2 Hz,
1H), 7.56–7.50 (m, 6H), 7.46–7.40 (m, 3H), 7.28–7.24 (m, 2H),
2.40 (s, 3H), ppm. 13C NMR (100 MHz, CDCl3): d 195.3, 147.6,
144.6, 143.9, 140.4, 136.3, 134.9, 134.1, 132.9, 131.5, 129.7,
129.1, 129.0, 128.5, 128.0, 126.0, 125.8, 124.3, 123.7, 119.7,
119.5, 22.0 ppm. HRMS (ESI): calcd for C24H16O: 321.1274 [M +
H+]; found 321.1300.
3-[2-(4-Nitro-phenyl)-vinyl]-2-phenyl-inden-1-one (8)
2-Methoxy-5-phenyl-benzo[a]uoren-11-one (2o)
Compound 8 was obtained as a byproduct in the reaction of yne-
Red-orange solid. Yield: 62% (52 mg). Mp: 189–191 ꢀC. 1H NMR enone 1f. Orange solid. Yield: 28% (25 mg). Mp: 115–117 ꢀC. 1H
(400 MHz, CDCl3): d 8.45 (d, J ¼ 2.4 Hz, 1H),7.68 (d, J ¼ 9.2 Hz, NMR (400 MHz, CDCl3): d 8.24 (d, J ¼ 8.8 Hz, 2H), 7.63–7.61 (m,
1H), 7.62 (d, J ¼ 7.2 Hz, 1H), 7.55–7.48 (m, 5H), 7.47–7.41 (m, 4H), 7.55 (s, 1H), 7.55–7.47 (m, 5H), 7.46–7.40 (m, 2H), 7.35 (t, J
3H), 7.29 (dd, J ¼ 7.4, 3.8 Hz, 1H), 7.00 (dd, J ¼ 6.0, 4.6 Hz, 1H), ¼ 8.0 Hz, 1H), ppm. 13C NMR (100 MHz, CDCl3): d 195.4, 149.3,
4.0 (s, 3H) ppm. 13C NMR (100 MHz, CDCl3): d 194.3, 158.8, 147.7, 143.2, 142.7, 135.9, 134.1, 133.5, 131.5, 130.8, 130.2,
147.4, 144.6, 142.8, 134.1, 133.2, 131.8, 131.6, 130.1, 128.4, 129.2, 128.7, 128.5, 127.7, 125.7, 124.3, 123.3, 121.5 ppm. HRMS
128.2, 126.1, 125.4, 123.7, 122.9, 119.0, 118.5, 113.1, 54.5 ppm. (ESI): calcd for C23H15NO3: 354.1125 [M + H+]; found 354.1121.
HRMS (ESI): calcd for C24H16O2: 337.1223 [M + H+]; found Compound 8 was converted into 2f in 55% yield when heated
337.1233.
under reux in AcOH for 24 h.
23656 | RSC Adv., 2019, 9, 23652–23657
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