11
(19), 95 (43), 42 (27); Anal. Calcd for C H O : C, 79.97; H,
6.71. Found: C, 79.91; H, 6.77.
4.5.30. 4-[7-Chloro-3-(5-methylfuran-2-yl)-1-benzofuran-2-
yl]butan-2-one (10r)
ACCEPTED MANUSCRIPT
24 24
3
Colorless oil; 362 mg, 80% yield; Rf
=
0.55 (ethyl
4.5.26. 4-[6-Methyl-3-(5-methylfuran-2-yl)-1-benzofuran-2-
yl]butan-2-one (10p)
1
acetate/petroleum ether = 1:3); Н NMR (400 MHz, CDCl3): δ =
7.68 (d, 3J = 7.5 Hz, 1Н, HAr), 7.26 (d, 3J = 7.5 Hz, 1Н, HAr), 7.17
Colorless oil; 254 mg, 60% yield; Rf
= 0.47 (ethyl
3
3
(t, J = 7.5 Hz, 1H, HAr), 6.47(d, J = 3.0 Hz, 1H, HFur), 6.11 (d,
3J = 3.0 Hz, 1H, HFur), 3.34 (t, 3J = 7.5 Hz, 2H, CH2), 2.96 (t, 3J =
1
acetate/petroleum ether = 1:3); Н NMR (400 MHz, CDCl3): δ =
3
7.66 (d, J = 7.5 Hz, 1Н, HAr), 7.23 (br s, 1Н, HAr), 7.09 (br d, 3J
7.5 Hz, 2Н, CН2), 2.39 (s, 3Н, CН3), 2.22 (s, 3Н, CН3) ppm; 13
C
3
3
= 7.5 Hz, 1H, HAr), 6.47 (d, J = 3.0 Hz, 1H, HFur), 6.12 (d, J =
3.0 Hz, 1H, HFur), 3.32 (t, 3J = 7.5 Hz, 2H, CH2), 2.93 (t, 3J = 7.5
Hz, 2Н, CН2), 2.48 (s, 3Н, CН3), 2.40 (s, 3Н, CН3), 2.20 (s, 3Н,
CН3) ppm; 13C NMR (100 MHz, CDCl3): δ = 207.1, 154.5,
152.5, 151.3, 146.2, 134.3, 124.3, 120.1, 111.2, 108.4, 107.6,
107.2, 106.3, 41.5, 29.9, 22.4, 21.7, 13.7 ppm; MS (EI, 70 eV):
m/z (%) = 282 (M+, 41), 239 (13), 225 (100), 175 (20), 135 (38),
108 (14), 78 (13), 57 (36), 43 (22); Anal. Calcd for C18H18O3: C,
76.57; H, 6.43. Found: C, 76.58; H, 6.55.
NMR (100 MHz, CDCl3): δ = 206.7, 154.0, 151.7, 149.8, 145.2,
128.5, 124.3, 123.9, 119.2, 116.5, 109.3, 108.2, 107.3, 41.1, 29.9,
22.3, 13.7 ppm; MS (EI, 70 eV): m/z (%) = 304/302 (M+, 30/95),
247/245 (30/100), 197 (25), 152 (25), 115 (17), 42 (74); Anal.
Calcd for C17H15ClO3: C, 67.44; H, 4.99. Found: C, 67.21; H,
5.09.
4.5.31.
dihydro-4H-furo[2’,3’:3,4]cyclohepta[1,2-b][1]benzofuran (11r)
Colorless oil; 82 mg, 15% yield; Rf 0.82 (ethyl
8-Chloro-2,4-dimethyl-4-(5-methylfuran-2-yl)-5,6-
=
4.5.27. 2,4,9-Trimethyl-4-(5-methylfuran-2-yl)-5,6-dihydro-4H-
furo[2’,3’:3,4]cyclohepta[1,2-b][1]benzofuran (11p)
1
acetate/petroleum ether = 1:3); Н NMR (400 MHz, CDCl3): δ =
8.04 (d, 3J = 7.5 Hz, 1Н, HAr), 7.25 (d, 3J = 7.5 Hz, 1Н, HAr), 7.20
Yellow oil; 182 mg, 35% yield; Rf
=
0.81 (ethyl
3
3
(t, J = 7.5 Hz, 1H, HAr), 5.97 (s, 1H, HFur), 5.78 (d, J = 3.0 Hz,
1H, HFur), 5.69 (d, 3J = 3.0 Hz, 1H, HFur), 3.12 (ddd, 2J = 18.0 Hz,
1
acetate/petroleum ether = 1:3); Н NMR (400 MHz, CDCl3): δ =
3
8.02 (d, J = 8.0 Hz, 1Н, HAr), 7.21 (br s, 1H, HAr), 7.12 (br d, 3J
3J = 2.5 Hz, 3J = 7.5 Hz, 1H, CH2), 2.86 (ddd, J = 18.0 Hz, 3J =
2
3
= 8.0 Hz, 1H, HAr), 5.98 (s, 1H, HFur), 5.81 (d, J = 3.0 Hz, 1H,
3.0 Hz, 3J = 10.5 Hz, 1H, CH2), 2.47 (ddd, 2J = 14.0 Hz, 3J = 3.0
HFur), 5.73 (d, 3J = 3.0 Hz, 1H, HFur), 3.06 (ddd, 2J = 18.0 Hz, 3J =
3
Hz, J = 7.5 Hz, 1H, CH2), 2.39 (s, 3H, CH3), 2.26 (s, 3H, CH3),
3
2
3
2.5 Hz, J = 7.5 Hz, 1H, CH2), 2.83 (ddd, J = 18.0 Hz, J = 3.0
2.10 (ddd, 2J = 14.0 Hz, 3J = 3.0 Hz, 3J = 7.5 Hz, 1H, CH2), 1.65
(s, 3Н, CН3) ppm; 13C NMR (100 MHz, CDCl3): δ = 158.3,
154.4, 151.2, 150.1, 141.9, 128.2, 126.6, 124.0, 123.8, 120.3,
116.2, 110.1, 108.1, 107.1, 105.8, 39.0, 34.6, 29.8, 27.4, 25.5,
13.8, 13.7 ppm; MS (EI, 70 eV): m/z (%) = 368/366 (M+,
32/100), 351 (20), 284 (18), 269 (46), 95 (18), 57 (17), 42 (57);
Anal. Calcd for C22H19ClO3: C, 72.61; H, 5.22. Found: C, 72.81;
H, 5.17.
3
2
Hz, J = 10.5 Hz, 1H, CH2), 2.49 (s, 3H, CH3), 2.46 (ddd, J =
3
3
13.5 Hz, J = 3.0 Hz, J = 7.5 Hz, 1H, CH2), 2.41 (s, 3H, CH3),
2.28 (s, 3H, CH3), 2.11 (ddd, 2J = 13.5 Hz, 3J = 2.5 Hz, 3J = 10.5
Hz, 1H, CH2), 1.66 (s, 3H, CH3) ppm; 13C NMR (100 MHz,
CDCl3): δ = 158.6, 154.6, 153.0, 151.0, 149.6, 142.9, 133.9,
125.7, 124.2, 124.1, 121.1, 111.0, 109.1, 108.0, 107.0, 105.8,
39.0, 34.8, 27.3, 25.5, 21.7, 13.8, 13.7 ppm; MS (EI, 70 eV): m/z
(%) = 346 (M+, 100), 331 (17), 303 (17), 263 (22), 249 (88), 95
(10), 42 (51); Anal. Calcd for C23H22O3: C, 79.74; H, 6.40.
Found: C, 79.51; H, 6.31.
4.5.32. 7-[(4-Methylphenyl)sulfonyl]-2,4-dimethyl-5,6-dihydro-
4H-furo[2,3:3,4]cyclohepta[1,2-b]indole (11s)
White solid; 298 mg, 41% yield; mp 158–159 °C
(benzene/methanol); Rf = 0.83 (ethyl acetate/petroleum ether =
4.5.28. 4-[6,7-Dimethyl-3-(5-methylfuran-2-yl)-1-benzofuran-2-
yl]butan-2-one (10q)
1
1:3); Н NMR (400 MHz, CDCl3): δ = 8.32–8.25 (m, 2H, HAr),
Yellow oil; 138 mg, 31% yield; Rf
=
0.48 (ethyl
7.53 (d, 3J = 8.0 Hz, 2H, HAr), 7.33–7.31 (m, 2H, HAr), 7.12 (d, 3J
1
acetate/petroleum ether = 1:5); Н NMR (400 MHz, CDCl3): δ =
7.49 (d, 3J = 8.0 Hz, 1H, HAr), 7.07 (d, 3J = 8.0 Hz, 1H, HAr), 6.46
(d, 3J = 3.0 Hz, 1H, HFur), 6.11 (d, 3J = 3.0 Hz, 1H, HFur), 3.34 (t,
3J = 7.5 Hz, 2H, CH2), 2.94 (t, 3J = 7.5 Hz, 2Н, CН2), 2.42 (s, 3Н,
CН3), 2.39 (s, 6Н, 2 CН3), 2.22 (s, 3Н, CН3) ppm; 13C NMR (100
MHz, CDCl3): δ = 207.3, 153.6, 152.3, 151.2, 146.4, 132.5,
124.2, 119.5, 117.1, 108.8, 107.5, 107.2, 106.1, 41.7, 29.9, 22.5,
19.2, 13.7, 11.7 ppm; MS (EI, 70 eV): m/z (%) = 296 (M+, 68),
253 (9), 239 (100), 211 (7), 58 (9), 42 (26); Anal. Calcd for
C19H20O3: C, 77.00; H, 6.80. Found: C, 77.11; H, 6.72.
3
= 8.0 Hz, 2H, HAr), 6.02 (s, 1H, HFur), 5.80 (d, J = 3.0 Hz, 1H,
3
HFur), 5.68 (d, J = 3.0 Hz, 1H, HFur), 3.64–3.58 (m, 1H, CH2),
3.00–2.93 (m, 1H, CH2), 2.47–2.41 (m, 1H, CH2), 2.39 (s, 3H,
CH3), 2.31 (s, 3H, CH3), 2.29 (s, 3H, CH3), 2.02–1.96 (m, 1H,
CH2), 1.63 (s, 3Н, CН3) ppm; 13C NMR (100 MHz, CDCl3): δ =
158.5, 151.0, 150.0, 144.6, 143.4, 137.0, 136.0, 135.9, 129.8
(2C), 128.0, 127.7, 126.4 (2C), 124.5, 124.1, 121.9, 115.2, 114.4,
108.3, 107.1, 105.7, 39.0, 36.5, 27.6, 24.7, 21.5, 13.8, 13.7 ppm;
MS (EI, 70 eV): m/z (%) = 485 (M+, 49), 330 (100), 316 (26),
249 (27), 234 (15), 91 (31), 42 (68); Anal. Calcd for
C29H27NO4S: C, 71.73; H, 5.60; N, 2.88; S, 6.60. Found: C,
71.70; H, 5.70; N, 3.00; S, 6.81.
4.5.29. 2,4,8,9-Tetramethyl-4-(5-methylfuran-2-yl)-5,6-dihydro-
4H-furo[2’,3’:3,4]cyclohepta[1,2-b][1]benzofuran (11q)
Yellow oil; 173 mg, 32% yield; Rf
=
0.83 (ethyl
4.5.33.
9,10-Ethylenedioxy-7-[(4-methylphenyl)sulfonyl]-2,4-
1
acetate/petroleum ether = 1:3); Н NMR (400 MHz, CDCl3): δ =
7.86 (d, 3J = 8.0 Hz, 1H, HAr), 7.10 (d, 3J = 8.0 Hz, 1H, HAr), 5.97
(s, 1H, HFur), 5.80 (d, 3J = 3.0 Hz, 1H, HFur), 5.72 (d, 3J = 3.0 Hz,
dimethyl-5,6,9,10-tetrahydro-4H-furo[2,3:3,4]cyclohepta[1,2-
b]indole (11t)
Colorless oil; 326 mg, 40% yield; Rf
acetate/petroleum ether = 1:3); Н NMR (400 MHz, CDCl3): δ =
7.78 (s, 1H, HAr), 7.73 (s, 1H, HAr), 7.49 (d, 3J = 8.0 Hz, 2H, HAr),
7.12 (d, 3J = 8.0 Hz, 2H, HAr), 5.97 (s, 1H, HFur), 5.78 (d, 3J = 3.0
= 0.75 (ethyl
2
3
3
1H, HFur), 3.08 (ddd, J = 18.0 Hz, J = 2.5 Hz, J = 7.5 Hz, 1H,
1
2
3
3
CH2), 2.84 (ddd, J = 18.0 Hz, J = 3.0 Hz, J = 11.0 Hz, 1H,
CH2), 2.47 (ddd, 2J = 14.0 Hz, 3J = 3.0 Hz, 3J = 7.5 Hz, 1H, CH2),
2.42 (s, 3H, CH3), 2.41 (s, 6H, 2 CH3), 2.28 (s, 3H, CH3), 2.11
3
Hz, 1H, HFur), 5.63 (d, J = 3.0 Hz, 1H, HFur), 4.29 (s, 4H, 2
2
3
3
(ddd, J = 14.0 Hz, J = 2.5 Hz, J = 11.0 Hz, 1H, CH2), 1.66 (s,
3Н, CН3) ppm; 13C NMR (100 MHz, CDCl3): δ = 158.6, 153.6,
152.8, 151.0, 149.5, 143.1, 132.1, 125.5, 124.9, 124.0, 119.2,
118.2, 109.5, 107.9, 107.0, 105.8, 38.9, 34.9, 27.3, 25.6, 19.2,
13.8, 13.7, 11.6 ppm; MS (EI, 70 eV): m/z (%) = 360 (M+, 100),
345 (10), 287 (14), 277 (18), 263 (94), 95 (11), 42 (43); Anal.
Calcd for C24H24O3: C, 79.97; H, 6.71. Found: C, 79.75; H, 6.70.
OCH2), 3.55–3.49 (m, 1H, CH2), ppm. 2.92–2.85 (m, 1H, CH2),
2.42–2.36 (m, 1H, CH2), 2.34 (s, 3H, CH3), 2.31 (s, 3H, CH3),
2.27 (s, 3H, CH3), 1.97–1.91 (m, 1H, CH2), 1.59 (s, 3Н, CН3)
ppm; 13C NMR (100 MHz, CDCl3): δ = 158.5, 151.0, 149.9,
144.5, 143.4, 141.9, 141.5, 135.9, 135.2, 131.9, 129.7 (2C),
127.5, 126.4 (2C), 122.2, 114.2, 109.0, 108.2, 107.0, 105.7,