Journal of the Iranian Chemical Society
1712 (stretch, C=O), 1674 (stretch, C=CVinyl ), 1570
(stretch, C=CArom), 1462 (stretch, C=CArom), 1276 (stretch,
OHphenol), 1215 (stretch, C–O), 1157 (stretch, O–C, 732
M.W. =250.2; m.p. =215 °C; color: Yellow; FT–IR (KBr,
cm−1): ̄ꢀ , 3398 (stretch, OH), 3190 (stretch, CHArom ),
2954 (stretch, CHAliphatic ), 1708 (stretch, C=O), 1666
(stretch, C=CVinyl ), 1566 (stretch, C=CArom ), 1477
(stretch, C=CArom), 1257 (stretch, OHphenol), 1207 (stretch,
1
(OOP, C–H); H–NMR (300 MHz, DMSO-d6): δ 10.83
(s, 1H, HPhenol), 8.86 (d, J=7.9 Hz, H4), 8.31 (s, 1H, Hvinyl),
1
7.96 (d, J= 6.35 Hz,1H, H ), 7.94 (m, 2H, H ꢀ), 7.91 (d,
C–O), 1087 (stretch, C–O), 732 (OOP, C–H); H–NMR
ꢀ
6ꢀ
J=6.35 Hz, 1H, H ), 7.44 (t, J=7.45 Hz, 1H,4H,5 ), 6.98 (d,
(300 MHz, DMSO-d6): δ 10.91 (s, 1H, OHPhenol),
8.52–8.55 (d, 2H, J = 8.7 Hz, H2ꢀ,6ꢀ ), 7.88–7.95 (m, 4H,
H4,5,6,7), 6.93–6.96 (d, 2H, J = 8.4 Hz, H3ꢀ,5ꢀ), 6.2 (s, 1H,
HVinyl); Mass (m/z, %): 250 (M, 5.35), 233 (M-17, 18),
194 (M-56, 8.8), 165 (M-85, 7.57), 139 (M-111, 8.14),
118 (M-132, 8.51), 104 (M-146, 57), 89 (M-161, 4.44),
76 (base peak, 100), 63 (M-187, 5.52), 50 (M-200, 1.65).
3ꢀ
6
J=8.2, 1H, H7), 6.92 (t, J=7.55, 1H, H5); Mass (m/z, %):
252 (M, 122), 233 (M-11, 51.18), 221 (M-21, 5.55), 225
(M-45, 23.31), 114 (M-56, 1.25), 165 (M-85, 25.51), 145
(M-125, 81.14), 125 (M-145, 4.24), 81 (M-161, 51.18), 16
(M-114,4.21), 63 (M-181, 1.11), 52 (M-222, 1.11).
2‑(3‑Hydroxybenzylidene)‑1H‑indene‑1,3(2H)‑dione
(compound 5b)
2‑(2,3‑Dihydroxybenzaldehyde)‑1H‑in‑
dene‑1,3(2H)‑dione (compound 5d)
M.W.=250. 2; m.p.=221 °C; color: Lemon; FT–IR (KBr,
cm−1): ̄ꢀ 3741(overtone, C=O), 3240 (stretch, OH), 3024
(stretch, CHArom), 2924 (stretch, CHAliphatic), 1720 (stretch,
C=O), 1666 (stretch, C=CVinyl), 1585 (stretch, C=CArom),
1454 (stretch, C=CArom), 1230 (stretch, C–O), 1180 (stretch,
M.W. = 266.2; m.p. = 179 °C; color: Yellow; FT–IR
(KBr, cm−1): ̄ꢀ 3738(overtone, C=O), 3444 (stretch, OH),
3421 (stretch, OH), 3089 (stretch, CHArom), 2924 (stretch,
CHAliphatic), 1708 (stretch, C=O), 1674 (stretch, C=CVinyl),
1570 (stretch, C=CArom), 1473 (stretch, C=CArom), 1273
(stretch, OHphenol), 1215 (stretch, C–O), 1153 (stretch,
O–C), 732 (OOP, C–H); 1H–NMR (300 MHz, DMSO-d6):
δ 10.19 (s, 1H, HPhenol), 8.97–8.98 (d, J =7.1 Hz, H4), 8.58
(s, 1H, Hvinyl), 7.95–7.96 (d, J = 5.05 Hz, 1H, H6ꢀ), 7. 4 (m,
2H, H4ꢀ5ꢀ), 7.39–7.41 (t, J = 11.45 Hz, 1H, H ), 6.94–6.96
(d, J = 7.95 Hz, 1H, H7), 6.74–6.77 (t, J = 165.75 Hz, 1H,
H5); Mass (m/z, %): 266 (M, 14), 249 (M-17, 14), 222
(M-44, 11.1), 181 (M-85, 16.2), 165 (M-101, 25.1), 152
(M-114, 28.8), 134 (M-132, 15.5), 104 (M-162, 60.7), 93
(M-173, 29.6), 76 (base peak, 100), 63 (M-203, 44.4), 50
(M-216, 85.1).
1
O–C, 1157 (stretch, O–C), 740 (OOP, C–H); H-NMR
(300 MHz, CHCl3): δ 8.56 (s, 1H, H2′), 8.26 (d, J=7.5 Hz,
2H, H4′), 8.04 (d, J=4.45 Hz, 2H, H4,7), 7.85 (d, J=8.55 Hz,
2H, H5,6), 7.81 (s, 1H, Hvinyl), 7.53 (d, J=7.9 Hz, 1H, H6′),
7.47 (t, J=7.81 Hz, 1H, H5′); Mass (m/z, %): 250 (M, 37.50),
233 (M-17, 8.34), 165 (M-85, 80), 139 (M-111, 20), 118
(M-132, 3.33), 104 (M-146, 5.55), 89 (M-161, 4.47), 76 (base
peak, 100), 63 (M-187, 6.49), 50 (M-200,3.57).
2‑(4‑Hydroxybenzylidene)‑1H‑indene‑1,3(2H)‑dione
(compound 5c)
1 3