2060
C.-F. Lin et al.
LETTER
2-(1-Anisolyl-1-pyridinylmethylenyl) Benzofuranone (2bg)
2-(1-Benzonitrilyl-1-phenylmethylenyl) Benzofuranone (2ad)
Compound 2ad was obtained in 87% yield. H NMR (200 MHz,
CDCl3): d = 7.87–7.60 (m, 4 H), 7.54–7.29 (m, 6 H), 7.25–7.15 (m,
3 H). 13C NMR (50 MHz, CDCl3): d = 183.3, 165.3, 143.8, 140.8,
137.7, 136.9, 136.3, 132.0, 131.8 131.6, 131.2, 131.0, 130.3, 129.6,
129.4, 128.4, 124.6, 123.4, 122.5, 118.7, 112.8, 112.4.
Compound 2bg was obtained in 99%. 1H NMR (200 MHz, CDCl3,
200 MHz): d = 8.76 (d, J = 4.0 Hz, 1 H), 7.83–7.75 (m, 1 H), 7.65–
7.56 (m, 4 H), 7.41–7.27 (m, 3 H), 7.14 (t, J = 7.4 Hz, 1 H), 6.95 (d,
J = 8.8 Hz, 2 H), 3.83 (s, 3 H). 13C NMR (100 MHz, CDCl3): d =
183.5, 165.2, 160.5, 155.1, 149.8, 143.9, 136.4, 136.3, 132.8, 132.1,
127.9, 125.6, 124.3, 123.0, 122.9, 122.6, 113.9, 113.8, 113.5, 112.6,
55.2.
1
MS (EI): m/z = 323 (59) (M+), 322 (100), 190 (10).
HRMS(EI): m/z calcd for C22H13NO2: 323.0947; found: 323.0941.
MS (EI): m/z = 313 (58) (M+), 298 (100), 201 (80).175 (44).
HRMS (EI): m/z calcd for C21H15NO3: 313.1104; found: 313.1065.
2-(1-Phenyl-1-trifluorobenzylmethylenyl) Benzofuranone (2ae)
Compound 2ae was obtained in 76% yield. H NMR (400 MHz,
1
2-(1-Phenyl-1-trfluorobenzylmethylenyl) Benzofuranone (2ca)
Compound 2ca and 3ca were obtained in 58% yield and they could
not be separated by liquid chromatography. The 1H NMR spectrum
showed a mixture of 2ca (36%) and 3ca (22%). The following spec-
trum belongs to 2ca. 1H NMR (400 MHz, CDCl3): d = 7.25 (td, J =
8.4, 0.8 Hz, 1 H), 7.18 (td, J = 7.6, 0.8 Hz 1 H), the other peaks of
aromatic could not be separated from those of 3ca.
CDCl3): d = 7.70–7.61 (m, 4 H), 7.55–7.53 (m, 2 H), 7.47–7.28 (m,
5 H), 7.21–7.17 (m, 2 H). 13C NMR (100 MHz, CDCl3): d = 136.7,
131.5, 131.3, 131.1, 130.8, 130.3, 129.4, 129.1, 128.8, 128.4, 128.3,
125.3, 125.2, 125.1, 125.1, 125.0, 124.6, 124.5, 123.4, 123.2, 112.7,
112.6.
MS (EI): m/z = 366 (57) (M+), 365 (100), 297 (13), 221 (35).
HRMS (EI): m/z calcd for C22H13O2F3: 366.0868; found: 366.0842.
2-(1-Anisolyl-1-trifluorobenzylmethylenyl) Benzofuranone
(2cb)
Compound 2cb was obtained in 28% yield. H NMR (400 MHz,
2-(1-Thienyl-1-phenylmethylenyl) Benzofuranone (2af)
Compound 2af was obtained in 35% yield. H NMR (200 MHz,
1
1
CDCl3): d = 7.67–7.60 (m, 3 H), 7.59–7.48 (m, 3 H), 7.39–7.35 (m,
3 H), 7.25–7.08 (m, 3 H). 13C NMR (50 MHz, CDCl3): d = 182.5,
164.5, 140.5, 136.1, 134.5, 133.6, 132.0, 130.3, 129.7, 129.6, 128.6,
128.4, 128.0, 127.4, 125.2, 124.3, 123.3, 123.2, 112.7.
CDCl3): d = 7.74–7.59 (m, 5 H), 7.41–7.29 (m, 2 H), 7.28–7.16 (m,
3 H), 6.96 (d, J = 6.8, 2.4 Hz, 2 H), 3.87 (s, 3 H). 13C NMR (100
MHz, CDCl3): d = 164.8, 160.6, 136.6, 134.1, 132.3, 131.5, 130.8,
130.6,130.3, 128.4, 128.3, 127.0, 125.3, 125.0, 124.9, 124.7,124.6,
123.7, 123.1, 113.7, 112.9, 112.6.
MS (EI): m/z = 304 (65) (M+), 303 (100), 184 (19).
MS (EI): m/z = 396 (100) (M+), 395 (91), 367 (25), 262 (17).
HRMS (EI): m/z calcd for C19H12SO2: 304.0559; found: 304.0546.
HRMS (EI): m/z calcd for C23H15O3F3: 396.0974; found: 396.0978.
2-(1-Anisolyl-1-phenylmethylenyl) Benzofuranone (2ba)
Compound 2ba was obtained in 92% yield. H NMR (200 MHz,
1
2-(1-Methylenyl-1-trifluorobenzyl) Benzofuranone (3c)
Compound 3c were obtained in 22% and 37% yields, respectively;
1H NMR (400 MHz, CDCl3): d = 8.25 (dd, J = 8.0, 0.4 MHz, 1 H),
8.23–8.04 (m, 2 H), 7.81–7.72 (m, 3 H), 7.61 (d, J = 1.2 Hz, 1 H),
7.59–7.43 (m, 1 H), 6.87 (s, 1 H). 13C NMR (100 MHz, CDCl3):
d = 184.6, 166.3, 147.8, 137.3, 135.7, 131.4, 130.8, 125.8, 125.7,
125.6, 124.8, 123.8, 121.3, 112.9, 112.6, 110.6.
CDCl3): d = 7.72 (d, J = 0.4 Hz, 1 H), 7.61–7.59 (m, 2 H), 7.58–7.51
(m, 2 H), 7.50& ndash;7.40 (m, 3 H), 7.39–7.13 (m, 3 H), 6.95 (d,
J = 9.2 Hz, 2 H), 3.86 (s, 3 H). 13C NMR (100 MHz, CDCl3): d =
183.0, 164.8, 160.4, 138.0, 135.9, 133.2, 132.3, 131.3, 130.3, 129.7,
129.1, 128.6, 128.2, 128.0, 124.5, 124.4, 123.3, 122.7, 113.6, 113.5,
112.5, 55.3.
MS (EI): m/z = 328 (99) (M+), 327 (100), 297 (17), 284 (12).
MS (EI): m/z = 290 (80) (M+), 289 (100), 221 (71).
HRMS (EI): m/z calcd for C22H16O3: 328.1099; found: 328.1104.
HRMS (EI): m/z calcd for C16H9O2F3: 290.0555; found: 290.0552.
2-(1,1-Dianisolylmethylenyl) Benzofuranone (2bb)
Compound 2bb was obtained in 85% yield. H NMR (200 MHz,
2-(1-Methylbenzoylmethylenyl) Benzofuranone (3d)
Compound 3d was obtained in 85% yield. H NMR (400 MHz,
1
1
CDCl3): d = 7.72–7.69 (m, 1 H), 7.68–7.48 (m, 3 H), 7.31–7.11 (m,
4 H), 6.98–6.91 (m, 4 H), 3.87 (d, J = 2.2 Hz, 6 H). 13C NMR (50
MHZ, CDCl3): d = 183.0, 164.8, 160.6, 160.5, 143.3, 136.1, 133.7,
133.6, 133.5, 132.4, 132.3, 130.3, 128.1, 124.5, 123.7, 122.8, 113.8,
113.7, 113.6, 112.7, 55.5, 55.4.
CDCl3): d = 8.25–8.20 (m, 3 H), 8.19–8.00 (m, 2 H), 7.99–7.71 (m,
1 H), 7.61–7.59 (m, 1 H), 7.47–7.42 (m, 1 H), 6.89 (s, 1 H), 3.97 (s,
3 H). 13C NMR (100 MHz, CDCl3): d = 178.2, 166.1, 162.0, 156.2,
135.7, 134.0, 132.6, 130.1, 126.2, 126.1, 125.7, 125.4, 123.9, 118.1,
108.7, 52.4, 29.6.
MS (EI): m/z = 358 (100) (M+), 357 (67), 327 (21), 238 (8).
MS (EI): m/z = 280 (20) (M+), 247 (100), 220 (15), 189 (18).
HRMS (EI): m/z calcd for C23H18O4: 358.1205; found: 358.1205.
HRMS (EI): m/z calcd for C17H12O4: 280.0735; found: 280.0736.
2-(1-Anisolyl-1-benzonitrilylmethylenyl) Benzofuranone (2bd)
Compound 2bd was obtained in 91% yield. H NMR (400 MHz,
3-Thienyl Flavone (5af)
Compound 5af was obtained in 52% yield. H NMR (200 MHz,
1
1
CDCl3): d = 7.72 (dd, J = 8.4, 2.0 Hz, 2 H), 7.68–7.61 (m, 2 H), 7.50
(dd, J = 6.8, 2.0 Hz, 2 H ), 7.43 (dd, J = 6.4, 2.0 Hz, 2 H), 7.30 (dd,
J = 8.4, 0.8 Hz, 2 H), 7.20–7.16 (m, 1 H), 6.95 (dd, J = 6.8, 2.0 Hz,
2 H), 3.86 (s, 3 H). 13C NMR (100 MHz, CDCl3): d = 165.0, 160.7,
143.0, 141.1, 136.6, 133.0, 132.1, 132.0, 131.7, 131.3, 131.2, 129.3,
128.4, 124.5, 123.2, 122.7, 118.7, 114.1, 114.0, 112.7, 112.2, 55.3,
31.9.
CDCl3): d = 7.79 (d, J = 0.6 Hz, 1 H), 7.63–7.43 (m, 8 H), 7.21–7.10
(m, 3 H). 13C NMR (50 MHz, CDCl3): d = 182.5, 164.5, 140.5,
137.9, 136.2, 134.5, 133.5, 132.0, 131.5, 130.3, 129.7, 128.9, 128.6,
128.4, 128.0, 124.4, 123.3, 122.8, 112.6.
MS (EI): m/z = 304 (66) (M+), 303(100), 184(16).
HRMS (EI): m/z calcd for C19H12SO2: 304.0559; found: 304.0546.
MS (EI): m/z = 353 (91) (M+), 352 (100), 338 (15), 322 (35), 190
(11)
2-(1-Phenyl-propanonyl)-1-methylphenyl Ether (8)
Compound 8 was obtained in 93% yield. H NMR (200 MHz,
1
HRMS (EI): m/z calcd for C23H15NO3: 353.1053; found: 353.1053.
CDCl3): d = 8.07 (dd, J = 8.0, 1.8 Hz, 1 H), 7.55–7.27 (m, 11 H),
7.10–7.02 (m, 2 H), 5.24 (s, 2 H). 13C NMR (50 MHz, CDCl3): d =
176.8, 158.7, 136.2, 134.7, 132.9, 132.8, 132.1, 130.1, 128.6, 128.5,
Synlett 2003, No. 13, 2057–2061 © Thieme Stuttgart · New York