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S. Chimichi et al. / Tetrahedron 59 (2003) 5215–5223
ether); IR (KBr) 3042, 1687 (CvO), 1634, 1562, 1234,
1
(18), 178 (100), 153 (24). Anal. calcd for C23H18O2: C,
84.64; H, 5.56. Found: C, 84.86; H, 5.38.
97600cm21; H NMR (200 MHz, CDCl3) d 8.95 (m, 1H,
0
3
H-300), 8.22 (d, 1H, J¼16.0 Hz, H-2 ), 8.22–8.18 (m, 2H,
H-5 , H-800), 7.82–7.75 (m, 1H, H-600/H-700), 7.69–7.60 (m,
2H, H-700/H-600, H-200), 7.11 (d, 1H, 3J¼16.0 Hz, H-10), 5.72
(s, 1H, H-4), 1.50 (s, 6H, 2£2-CH3); 13C NMR (75.43 MHz,
CDCl3) d 206.8, 179.7, 150.0, 148.7, 140.0, 132.3, 130.2,
129.7, 127.2, 125.9, 123.1, 122.4, 117.8, 103.8, 88.8, 23.1,
10.4; EI-MS m/z (%) 265 (Mþ, 9), 206 (14), 179 (100), 151
(27). Anal. calcd for C17H15NO2: C, 76.96; H, 5.70; N, 5.28.
Found: C, 77.17; H, 5.56; N, 5.09.
4.4.11. 2-Methyl-5-[(E)-2-(2-naphtyl)ethenyl]-2-phenyl-
3(2H)-furanone 15. Operating as for 9, starting from
2-naphthaldehyde and 6d the 3(2H)-furanone 15 was
obtained as a yellowish solid after purification by flash-
chromatography (ethyl acetate/petroleum ether¼1:5 v/v as
eluant); yield 36%; mp 105–1068C (petroleum ether); IR
(KBr) 1689 (CvO), 1622, 1552, 1369 cm21 1H NMR
;
(200 MHz, CDCl3) d 8.00–7.28 (m, 12H, Ar), 7.84 (d, 1H,
3J¼15.8 Hz, H-20), 7.06 (d, 1H, 3J¼15.8 Hz, H-10), 5.66 (s,
1H, H-4), 1.86 (s, 3H, 2-CH3); 13C NMR (75.43 MHz,
CDCl3) d 204.0, 181.7, 139.1, 138.6, 134.1, 133.3, 132.1,
130.1, 128.8, 128.5, 128.0, 127.8, 127.3, 126.8, 124.5,
123.2, 116.2, 102.0, 89.9, 24.3; EI-MS m/z (%) 326 (Mþ,
10), 205 (6), 194 (72), 178 (100), 151 (67). Anal. calcd for
C23H18O2: C, 84.64; H, 5.56. Found: C, 84.43; H, 5.67.
4.4.8. 2-Methyl-2-phenyl-5-[(E)-2-phenylethenyl]-3(2H)-
furanone 12. Operating as for 9, starting from benzal-
dehyde and 6d the 3(2H)-furanone 12 was obtained as a
yellowish crystals after purification by flash-chromato-
graphy (ethyl acetate/petroleum ether¼1:7, v/v as eluant);
yield 54%; mp 85.0–85.58C (hexane); IR (KBr) 3088, 1686
(CvO), 1629, 964, 699 cm21; 1H NMR (300 MHz, CDCl3)
d 7.68 (d, 1H, 3J¼16.1 Hz, H-20), 7.62–7.32 (m, 10H, Ar),
4.4.12. 2-Methyl-2-phenyl-5-[(E)-2-(4-quinolinyl)-
ethenyl]-3(2H)-furanone 16. Operating as for 11, starting
from 6d the 3(2H)-furanone 16 was obtained as a yellowish
crystals after purification by flash-chromatography (ethyl
acetate/petroleum ether¼5:1 v/v as eluant); yield 40%; mp
168–1698C (hexane); IR (KBr) 3064, 1693 (CvO), 1629,
1562, 1237, 961 cm21; 1H NMR (200 MHz, CDCl3) d 8.98
0
3
6.95 (d, 1H, J¼16.1 Hz, H-1 ), 5.64 (s, 1H, H-4), 1.85 (s,
3H, 2-CH3); 13C NMR (75.43 MHz, CDCl3) d 204.0 (s,
C-3), 1080 1.6 (s, C-5), 139.0 (d, C-20), 1380.05 (s, C-1000), 134.6
(s, C-1 ), 130.3 (d, C-400), 128.9 0(0d, C-3 , C-500), 128.4 (d,
C-3000, C-5000), 128.0 (d, C-200, C-6 ), 127.9 (d, C-4000), 124.5
(d, C-2000, C-6000), 116.1 (d, C-10), 102.0 (d, C-4), 89.9 (s,
C-2), 24.2 (q, 2-CH3); EI-MS m/z (%) 276 (Mþ, 67), 207
(61), 128 (100), 102 (49), 77 (71). Anal. calcd for C19H16O2:
C, 82.58; H, 5.84. Found: C, 82.29; H, 5.82.
00
0
3
3
(d, 1H, J¼4.8 Hz, H-3 ), 8.39 (d, 1H, J¼16.0 Hz, H-2 ),
8.25–8.18 (m, 2H, H-500, H-800), 7.84–7.76 (m, 1H, H-600/H-
700),070 .74–7.62 (m, 1H, H-700/H-600), 7.65 (d, 3J¼4.8 Hz, 1H,
3
H-20 ), 7.60–7.30 (m, 5H, Ar), 7.19 (d, J¼16.0 Hz, 1H,
4.4.9. 5-[(E)-2-(4-fluorophenyl)ethenyl]-2-methyl-2-
phenyl-3(2H)-furanone 13. Operating as for 9, starting
from 4-fluorobenzaldehyde and 6d the 3(2H)-furanone 13
was obtained as a yellowish crystals after purification by
flash-chromatography (ethyl acetate/petroleum ether¼2:7
v/v as eluant); yield 54%; mp 118.5–119.08C (hexane); IR
(KBr) 3089, 1689 (CvO), 1629, 1592, 1230, 968 cm21; 1H
NMR (300 MHz, CDCl3) d 7.63 (d, 1H, 3J¼16.1 Hz, H-20),
7.58–7.31 (m, 7H, Ar), 7.14–7.09 (m, 2H, Ar), 6.86 (d, 1H,
3J¼16.1 Hz, H-10), 5.62 (s, 1H, H-4), 1.84 (s, 3H, 2-CH3):
13C NMR (75.43 MHz, CDCl3) d 203.9 (s, C-3), 181.4 (s,
H-1 ), 5.77 (s, 1H, H-4), 1.88 (s, 3H, 2-CH3); 13C NMR
(75.43 MHz, CDCl3) d 203.8, 179.9, 149.6, 148.3, 139.7,
137.9, 132.4, 129.9, 129.6, 128.3, 127.9, 127.1, 125.7,
124.3, 122.8, 121.9, 117.6, 103.7, 90.0, 24.1; EI-MS m/z (%)
327 (Mþ, 3), 206 (15), 179 (100), 151 (25). Anal. calcd for
C22H17NO2: C, 80.71; H, 5.23; N, 4.28. Found: C, 80.87; H,
5.12; N, 4.47.
4.4.13. 2-(4-Fluorophenyl)-2-methyl-5-[(E)-2-phenyl-
ethenyl]-3(2H)-furanone 17. Operating as for 9, starting
from benzaldehyde and 6d the 3(2H)-furanone 12 was
obtained as a yellowish crystals after purification by flash-
chromatography (ethyl acetate/petroleum ether¼1:4 v/v as
eluant); yield 60%; mp 70–718C (petroleum ether); IR
C-5), 163.8 (d, JC,F¼252.0 Hz, C-400), 138.5 (s, C-1000),
1
0
137.6 (d, C-2 ), 130.9 (d, JC,F¼3.5 Hz, C-100), 129.8 (dd,
4
3JC,F¼8.5 Hz, C-200, C-600), 128.4 (d, C-3000, C-5000), 128.0 (d,
000
000
000
2
C-400 ), 124.5 (d, C-2 , C-6 ), 116.1 (dd, JC,F¼22.0 Hz,
C-3 , C-500), 115.8 (dd, 6JC,F¼2.4 Hz, C-10), 102.0 (d, C-4),
89.9 (s, C-2), 24.2 (q, 2-CH3); EI-MS m/z (%) 294 (Mþ,10),
225 (10), 147 (12), 146 (100), 77 (5). Anal. calcd for
C19H15FO2: C, 77.54; H, 5.14. Found: C, 77.65; H, 5.19.
(KBr) 3082, 1695 (CvO), 1631, 1218, 985, 756, 690 cm21
;
1H NMR (200 MHz, CDCl3) d 7.66 (d, 1H, H-20), 7.63–7.42
3
(m, 7H,0Ar), 7.10–7.01 (m, 2H, Ar), 6.94 (d, J¼16.1 Hz,
1H, H-1 ), 5.63 (s, 1H, H-4), 1.81 (s, 3H, 2-CH3); 13C NMR
(75.43 MHz, CDCl3) d 203.9 (s, C-3), 181.7 (s, C-5), 162.5
(d, 1JC,F¼246.8 Hz, C-4000), 139.2 (d, C-20), 134.6 (s, C-100),
134.4 (d, JC,F¼3.0 Hz, C-1000), 130.4 (d, C-400), 129.0 (d,
4
4.4.10. 2-Methyl-5-[(E)-2-(1-naphtyl)ethenyl]-2-phenyl-
3(2H)-furanone 14. Operating as for 9, starting from 6d
the 3(2H)-furanone 14 was obtained as a yellowish crystals
after purification by flash-chromatography (ethyl acetate/
petroleum ether¼1:5 v/v as eluant); yield 37%; mp 136–
1378C (petroleum ether); IR (KBr), 3058, 1687 (CvO),
1626, 1552, 1126 cm21;01H NMR (200 MHz, CDCl3) d 8.51
(d, 1H, 3J¼15.8 Hz, H-2 ), 8.28–7.24 (m, 12H, Ar), 7.06 (d,
1H, 3J¼15.8 Hz, H-10), 5.68 (s, 1H, H-4), 1.89 (s, 3H,
2-CH3); 13C NMR (75.43 MHz, CDCl3) d 204.2, 181.7,
138.7, 135.7, 133.8, 131.9, 131.5, 130.8, 128.9, 128.7,
128.2, 127.1, 126.4, 125.6, 125.1, 124.8, 123.2, 118.6,
102.4, 90.2, 24.4; EI-MS m/z (%) 326 (Mþ, 2), 205 (5), 195
C-300, C500), 128.0 (d, C-200, C-600), 126.4 (dd, 3JC,F¼8.2 Hz,
000
000
0
2
C-2 , C-6 ), 116.0 (d, C-1 ), 115.4 (dd, JC,F¼21.6 Hz,
C-3000, C-5000), 102.0 (d, C-4), 89.5 (s, C-2), 24.5 (q, 2-CH3);
EI-MS m/z (%) 294 (Mþ, 5), 225 (11), 129 (11), 128 (100),
127 (10), 102 (9), 77 (7). Anal. calcd for C19H15FO2: C,
77.54; H, 5.14. Found: C, 77.36; H, 5.30.
4.4.14. 2-(4-Fluorophenyl)-5-[(E)-2-(4-fluorophenyl)-
ethenyl]-2-methyl-3(2H)-furanone 18. Operating as for
9, starting from 4-fluorobenzaldehyde and 6e the 3(2H)-
furanone 18 was obtained as a yellowish crystals after
purification by flash-chromatography (ethyl acetate/