The Journal of Organic Chemistry
ARTICLE
3-(3,5-Dimethoxyphenyl)-4,6-dimethoxy-2-phenyl-2,3-di-
hydro-1H-inden-1-one (17). Yield 91%, white solid, mp 107À109 °C;
1H NMR (300 MHz, CDCl3) δ 7.32À7.24 (m, 3H), 7.10 (d, 2H, J =
6.4 Hz), 6.90 (d, 1H, J = 2.1 Hz), 6.70 (d, 1H, J = 2.1 Hz), 6.32 (t, 1H, J =
2.2 Hz), 6.16 (d, 2H, J = 2.2 Hz), 4.49 (d, 1H, J = 2.7 Hz), 3.88 (s, 3H), 3.71
(s, 6H), 3.71À3.69 (m, 1H), 3.69 (s, 3H); 13C NMR (75 MHz, CDCl3)
δ 205.6, 162.2, 160.9, 157.9, 146.0, 139.5, 138.9, 137.8, 128.9, 127.9, 127.2,
106.6, 105.3, 98.3, 96.6, 65.0, 55.9, 55.7, 55.3, 51.9; HRMS (EI) calcd for
C25H24O5 [M+] 404.1624, found 404.1618.
2-(4-Methoxyphenyl)-3-phenyl-1H-inden-1-one (24). Yield
83%, light red-orange oil; 1H NMR (300 MHz, CDCl3) δ 7.89 (d, 1H, J =
7.4 Hz), 7.64 (t, 1H, J = 7.4 Hz), 7.48 (t, 1H, J = 7.4 Hz), 7.30 (d, 4H, J =
6.7 Hz), 7.09 (d, 2H, J = 6.3 Hz), 7.03 (d, 2H, J = 8.5 Hz), 6.86 (d, 2H, J =
8.6 Hz), 4.52 (d, 1H,J =4.9Hz), 3.79 (s, 3H), 3.76 (d, 1H,J =4.9Hz);13
C
NMR (75 MHz, CDCl3) δ 205.7, 158.9, 156.1, 142.7, 136.3, 135.5, 130.6,
129.5, 129.0, 128.4, 128.0, 127.3, 126.8, 124.1, 114.4, 64.1, 55.4, 55.1;
HRMS (EI) calcd for C22H18O2 [M+] 314.1307, found 314.1310.
3-Phenyl-2-(p-tolyl)-2,3-dihydro-1H-inden-1-one (25). Yield
76%, light red-orange oil; 1H NMR (300 MHz, CDCl3) δ 7.89 (d, 1H, J =
7.6 Hz), 7.64 (td, 1H, J = 7.6, 1.1 Hz), 7.48 (t, 1H, J = 7.4 Hz), 7.35À7.27
(m, 4H), 7.13 (d, 2H, J = 8.0 Hz), 7.09 (dd, 2H, J = 7.7, 1.7 Hz), 7.00
(d, 2H, J = 8.0 Hz), 4.56 (d, 1H, J = 4.9 Hz), 3.78 (d, 1H, J = 4.9 Hz), 2.33
(s, 3H); 13C NMR (75 MHz, CDCl3) δ 205.6, 156.3, 142.7, 137.0, 136.4,
135.6, 135.5, 129.7, 129.0, 128.4, 128.0, 127.3 126.8, 124.1, 64.5, 55.0, 21.2;
HRMS (EI) calcd for C22H18O [M+] 298.1358, found 298.1360.
2-(4-Chlorophenyl)-3-phenyl-2,3-dihydro-1H-inden-1-one
3-(3,5-Dimethoxyphenyl)-4,6-dimethoxy-2-(p-tolyl)-2,3-di-
hydro-1H-inden-1-one (18). Yield 76%, white solid, mp 70À75 °C;
1H NMR (300 MHz, CDCl3) δ 7.11 (d, 2H, J = 8.1 Hz), 6.98 (d, 2H, J =
8.0 Hz), 6.89 (d, 1H, J = 2.1 Hz), 6.70 (d, 1H, J = 2.1 Hz), 6.31 (t, 1H, J =
2.2 Hz), 6.15 (d, 2H, J = 2.2 Hz), 4.46 (d, 1H, J = 2.7 Hz), 3.88 (s, 3H), 3.71
(s, 6H), 3.69 (s, 3H), 3.67 (d, 1H, J = 2.7 Hz), 2.32 (s, 3H); 13C NMR (75
MHz, CDCl3) δ 205.7, 162.0, 160.8, 157.8, 146.0, 138.8, 137.7, 136.7,
136.4, 129.6, 127.7, 106.5, 105.2, 98.2, 96.5, 64.6, 55.8, 55.7, 55.2, 51.8, 21.1;
HRMS (EI) calcd for C26H26O5 [M+] 418.1780, found 418.1783.
2-(4-Chlorophenyl)-3-(3,5-dimethoxyphenyl)-4,6-dimeth-
oxy-2,3-dihydro-1H-inden-1-one (19). Yield 74%, white solid,
mp 66À69 °C; 1H NMR (300 MHz, CDCl3) δ 7.29 (s, 1H), 7.03 (d, 2H,
J = 8.5 Hz), 6.89 (d, 1H, J = 2.0 Hz), 6.70 (d, 1H, J = 2.0 Hz), 6.32 (t, 1H,
J = 2.2 Hz), 6.14 (d, 2H, J = 2.2 Hz), 4.42 (d, 1H, J = 2.9 Hz), 3.88 (s, 3H),
3.71 (s, 6H), 3.69 (s, 3H), 3.67 (d, 1H, J = 2.9 Hz); 13C NMR (75 MHz,
CDCl3) δ 205.0, 162.3 (s), 161.0, 157.9, 145.7, 138.6, 137.9, 137.5,
133.1, 129.4, 129.1, 106.8, 105.3, 98.6, 96.3, 64.3, 55.7, 55.8, 55.3, 51.8;
HRMS (EI) calcd for C25H23ClO5 [M+] 438.1234, found 438.1230.
3-(3,5-Dimethoxyphenyl)-4,6-dimethoxy-2-(4-(trifluoro-
methyl)phenyl)-2,3-dihydro-1H-inden-1-one (20). Yield 63%,
white solid, mp 46À48 °C; 1H NMR (300 MHz, CDCl3) δ 7.56 (d, 2H,
J = 8.2 Hz), 7.22 (d, 2H, J = 8.0 Hz), 6.90 (d, 1H, J = 1.9 Hz), 6.72 (d, 1H,
J = 2.0 Hz), 6.33 (t, 1H, J = 1.9 Hz), 6.14 (d, 2H, J = 2.1 Hz), 4.46 (d, 1H,
J = 2.9 Hz), 3.89 (s, 3H), 3.76 (d, 1H, J = 2.9 Hz), 3.72 (s, 6H), 3.69
(s, 3H); 13C NMR (75 MHz, CDCl3) δ 204.5, 162.3, 160.9, 157.8,
145.4, 143.2, 138.5, 137.4, 128.3, 125.9, 125.8, 125.8, 125.7, 106.8, 105.2,
98.3, 96.5, 64.5, 55.8, 55.7, 55.3, 51.6; HRMS (EI) calcd for C26H23F3O5
[M+] 472.1498, found 472.1495.
1
(26). Yield 61%, yellow solid, mp 79À81 °C; H NMR (300 MHz,
CDCl3) δ 7.89 (d, 1H, J = 7.5 Hz), 7.65 (td, 1H, J = 7.6, 0.9 Hz), 7.50 (t,
1H, J = 7.4 Hz), 7.37À7.27 (m, 6H), 7.08 (dd, 2H, J = 7.7, 1.7 Hz), 7.04
(d, 2H, J = 8.4 Hz), 4.51 (d, 1H, J = 5.0 Hz), 3.78 (d, 1H, J = 5.1 Hz); 13C
NMR (75 MHz, CDCl3) δ 204.6, 155.8, 142.1, 136.8, 136.0, 135.6, 133.1,
129.8, 129.0, 128.4, 127.9, 127.4, 126.7, 124.1, 64.0, 54.8; HRMS (EI)
calcd for C21H15ClO [M+] 318.0811, found 318.0801.
2-(3-Methoxyphenyl)-3-phenyl-2,3-dihydro-1H-inden-1-
one (27). Yield 74%, yellow oil; 1H NMR (300 MHz, CDCl3) δ 7.89
(d, 1H, J = 7.6 Hz), 7.64 (td, 1H, J = 7.5, 1.1 Hz), 7.48 (t, 1H, J = 7.5 Hz),
7.34À7.26 (m, 4H), 7.23 (dd, 1H, J = 8.2, 5.5 Hz), 7.09 (dd, 2H, J = 7.7,
1.6 Hz), 6.82 (dd, 1H, J = 8.0, 2.2 Hz), 6.69 (d, 1H, J = 7.6 Hz), 6.65 (t,
1H, J = 2.1 Hz), 4.58 (d, 1H, J = 4.7 Hz), 3.78 (d, 1H, J = 4.8 Hz), 3.75 (s,
3H); 13C NMR (75 MHz, CDCl3) δ 205.0, 159.9, 156.2, 142.6, 140.0,
136.2, 135.5, 129.9, 128.9, 128.3, 127.9, 127.2, 126.7, 124.1, 120.6, 114.3,
112.6, 64.6, 55.2, 54.8; HRMS (EI) calcd for C22H18O2 [M+] 314.1307,
found 314.1306.
3-Phenyl-2-(o-tolyl)-2,3-dihydro-1H-inden-1-one (28). Yield
1
66%, light red-orange solid, mp 121À123 °C; H NMR (300 MHz,
CDCl3) δ 7.91 (d, 1H, J = 7.7 Hz), 7.64 (td, 1H, J = 7.6, 1.1 Hz), 7.50
(t, 1H, J = 7.4 Hz), 7.29 (t, 4H, J = 7.0 Hz), 7.16À7.12 (m, 3H), 7.09
(dd, 2H, J = 7.4, 1.8 Hz), 6.93 (d, 1H, J = 6.2 Hz), 4.50 (d, 1H, J = 5.0 Hz),
4.03 (d, 1H, J = 5.1 Hz), 2.00 (s, 3H); 13C NMR (75 MHz, CDCl3) δ
205.8, 156.1, 142.6, 142.6, 137.4, 136.9, 136.4, 135.3, 130.7, 128.9, 128.3,
127.9, 127.2, 126.6, 126.4, 123.9, 55.0, 20.0; HRMS (EI) calcd for
C22H18O [M+] 298.1358, found 298.1355.
4-(3-(3,5-Dimethoxyphenyl)-4,6-dimethoxy-1-oxo-2,3-di-
hydro-1H-inden-2-yl)benzonitrile (21). Yield 60%, light yellow
solid, mp 65À68 °C; 1H NMR (300 MHz, CDCl3) δ7.60 (d, 2H, J=8.1Hz),
7.22 (d, 2H, J = 8.3 Hz), 6.89 (d, 1H, J = 2.0 Hz), 6.72 (d, 1H, J = 2.0 Hz),
6.33 (t, 1H, J = 2.2 Hz), 6.13 (d, 2H, J = 2.2 Hz), 4.44 (d, 1H, J = 2.9 Hz),
3.88 (s, 3H), 3.76 (d, 1H, J = 2.9 Hz), 3.72 (s, 6H), 3.69 (s, 3H); 13C NMR
(75 MHz, CDCl3) δ 204.1, 162.5, 161.1, 158.0, 145.3, 144.7, 138.4, 137.5,
132.8, 128.9, 118.8, 111.2, 107.0, 105.3, 98.4, 96.7, 64.8, 55.9, 55.8, 55.4, 51.6;
HRMS (EI) calcd for C26H23NO5 [M+] 429.1576, found 429.1582.
trans-2-(3,5-Dimethoxyphenyl)-4,6-dimethoxy-3-(4-meth-
oxyphenyl)-2,3-dihydro-1H-inden-1-one (22). Yield 74%, white
2-(Naphthalen-2-yl)-3-phenyl-2,3-dihydro-1H-inden-1-one
(29). Yield 86%, light red-orange solid, mp 55À57 °C; 1H NMR
(300 MHz, CDCl3) δ 7.93 (d, 1H, J = 7.8 Hz), 7.85À7.79 (m, 2H),
7.75 (dd, 1H, J = 6.0, 3.5 Hz), 7.67 (t, 1H, J = 7.4 Hz), 7.59 (s, 1H), 7.52
(t, 1H, J = 7.4 Hz), 7.45 (dq, 2H, J = 6.7, 3.5 Hz), 7.35À7.32 (m, 2H),
7.30À7.28 (m, 2H), 7.20 (dd, 1H, J = 8.4, 1.4 Hz), 7.11 (d, 1H, J =
2.0 Hz), 7.09 (s, 1H), 4.68 (d, 1H, J = 4.8 Hz), 3.97 (d, 1H, J = 4.9 Hz);
13C NMR (75 MHz, CDCl3) δ 205.3, 156.2, 142.5, 136.3, 135.9, 135.5,
133.6, 132.6, 129.0, 128.8, 128.4, 128.0, 127.8, 127.7, 127.2, 126.8, 126.2,
126.0, 125.8, 124.1, 64.9, 54.9; HRMS (EI) calcd for C25H18O [M+]
334.1358, found 334.1358.
1
solid, mp 163À164 °C; H NMR (300 MHz, CDCl3) δ 6.94 (d, 2H,
J = 8.6 Hz), 6.89 (d, 1H, J = 1.9 Hz), 6.79 (d, 2H, J = 8.7 Hz), 6.69 (d, 1H,
J = 1.9 Hz), 6.36 (t, 1H, J = 2.1 Hz), 6.24 (d, 2H, J = 2.1 Hz), 4.51 (d, 1H,
J = 2.5 Hz), 3.88 (s, 3H), 3.78 (s, 3H) 3.74 (s, 6H), 3.66 (s, 3H), 3.60
(d, 1H, J = 2.6 Hz); 13C NMR (125 MHz, CDCl3) δ 205.6, 162.1, 161.1,
158.3, 157.9, 141.7, 138.7, 138.6, 135.6, 128.1, 114.0, 106.7, 106.2, 99.1,
96.6, 65.5, 56.0, 55.8, 55.4, 55.3, 51.0; HRMS (EI) calcd for C26H26O6
[M+] 434.1729, found 434.1734.
3-Phenyl-2-(pyridin-3-yl)-2,3-dihydro-1H-inden-1-one(30).
The reaction was performed by following the typical procedure except for
3-bromopyridine (2.0 equiv) and NaOtBu (1.2 equiv) for 24 h to provide
2,3-Diphenyl-2,3-dihydro-1H-inden-1-one (23)26. Yield 76%,
1
1
light red-orange oil; H NMR (300 MHz, CDCl3) δ 7.89 (d, 1H, J =
30 in 30% yield as a yellow oil; H NMR (300 MHz, CDCl3) δ 8.54
7.6Hz), 7.63 (t, 1H,J = 7.4Hz), 7.49(dd, 1H, J =11.0, 3.9 Hz), 7.35À7.27
(m, 6H), 7.25 (dd, 1H, J = 4.6, 0.6 Hz), 7.11À7.07 (m, 4H), 4.57 (d, 1H,
J = 4.7Hz), 3.81 (d, 1H, J = 4.8 Hz); 13C NMR(75MHz, CDCl3) δ205.3,
156.2, 142.6, 138.6, 136.3, 135.5, 129.0, 128.9, 128.5, 128.4, 128.0, 127.3,
126.8, 124.1, 64.7, 55.0; HRMS (EI) calcd for C21H16O [M+] 284.1201,
found 284.1201.
(d, 1H, J = 4.2 Hz), 8.38 (s, 1H), 7.90 (d, 1H, J = 7.7 Hz), 7.67 (t, 1H, J =
7.5 Hz), 7.56À7.44 (m, 2H), 7.38À7.26 (m, 5H), 7.10 (dd, 2H, J = 7.4,
1.6 Hz), 4.55 (d, 1H, J = 5.3 Hz), 3.84 (d, 1H, J = 5.3 Hz); 13C NMR
(75 MHz, CDCl3) δ 204.1, 155.8, 150.0, 148.8, 141.8, 135.97, 135.91,
135.85, 129.3, 128.7, 128.0, 127.7, 126.8, 124.2, 123.9, 62.3, 54.6; HRMS
(EI) calcd for C20H15NO [M+] 285.1154, found 285.1144.
6616
dx.doi.org/10.1021/jo2009164 |J. Org. Chem. 2011, 76, 6611–6618