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Indandione 1 (146 mg, 1 mmol), benzaldehyde 2
(R1 = C6H5, 106 mg, 1 mmol) and I2 (10 mol%)
were taken in round bottomed flask containing 5
mL of DMSO and it was stirred at room
temperature for 2 h. Then, added equimolar
amount of 4-hydroxycoumarin 3 (R2 = H, 162
mg, 1 mmol) into the reaction mixture and
heated at 90 ˚C for 4 h (till completion of the
reaction
monitored
by
Thin
Layer
4. Johnson, A. W.; Gowda, G.; Hassanali, A.;
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Chromatography). After completion of the
reaction, the mixture was cooled to room
temperature and poured into a beaker containing
25 mL water. Then, aqueous solution of sodium
thiosulphate (5 ml of 5% solution) was added to
the reaction mixture to neutralise the iodine. The
crude product 4a was obtained by filtration and
purified by recrystallization from ethanol that
afforded the pure indeno [1,2-b] furan in 82%
yield. The structure of the compound was
ascertained from the spectroscopic data and
elemental analysis.
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Yield: 300 mg (82%); Light yellow solid; Rf
(Pet. Ether.60-80/EtOAc, 7:3) 0.65; mp. 274.2-
276.2˚C; 1H NMR (500 MHz, CDCl3) δ 8.16 (d,
J = 7.7 Hz, 1H), 7.96 (td, J = 7.6, 1.0 Hz, 1H),
7.87 (td, J = 7.6, 1.0 Hz, 1H), 7.81 (dd, J = 7.8,
1.5 Hz, 1H), 7.70 – 7.63 (m, 2H), 7.49 – 7.45
(m, 1H), 7.40 – 7.35 (m, 1H), 7.23 – 7.14 (m,
3H), 6.89 (d, J = 7.0 Hz, 2H), 5.06 (s, 1H); 13C
NMR (CDCl3, 125 MHz) δ 92.1, 102.7, 111.7,
116.9, 123.2, 123.8, 124.2 (2C), 124.5, 128.4
(2C), 128.5 (2C), 132.7, 133.2 (2C), 136.7,
137.2, 140.0, 141.6, 155.3, 158.6, 167.9, 193.2;
IR (KBr, cm-1) νmax:1176.8 ,1578.5, 1681.7,
1719.9, 3608.6; MS (ESI): 367.1 [M+H]+; Anal.
Cald. for C24H14O4 : C, 78.68; H, 3.85; Found:
C, 78.66; H, 3.87.
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2014, 16, 2888.
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O. S.; Sedov, A. L.; Solov'eva, N. P.; Traven, V.
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S. B.; Athimoolam, J.; Sundara, K.
Pharmacologyonline 2008, 2, 176.
17. General Procedure for preparation of
indeno[1,2-b]furans:
A
mixture of 1,3-