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80 mL of CH2Cl2 was added dropwise at 0–58C. Then the resulting solution
was stirred for 2 hr at room temperature and refluxed for additional 5 hr. The
insoluble solid was removed by filtration and the solution was concentrated to
a third of its volume. Then appropriate ether was added and the precipitate was
filtered to afford product as a white solid. Yield: 98%. M.p.: 52–538C. IR
(KBr, n, cm21): 1036 (P55O).
General Procedure for the Preparation of Compound 1a–i
The mixture of coumarin-3-carboxylic acid (1 mmol), (un)substituted
benzoic acid hydrazides (1 mmol), and PEG supported dichlorophosphate
(1.2 mmol) was mixed using a pestle and mortar until a fine and homogeneous
powder was obtained. Then the mixture was irradiated in a microwave oven
for 6–8 min irradiating time at 490-W power by means of 1 min irradiation
then 30 sec interval. The completion of reactions was monitored by TLC
using ethyl acetate, acetone, and petroleum ether (1 : 1 : 2) as eluent. Then dis-
tilled water (20 mL) was added to the resulting mixture, and the precipitate
was collected by filtration and recrystallized from EtOH to afford product.
The physical and spectral data of compounds are shown below:
1
1a. White solid. H NMR (CDCl3, 200 MHz) d 8.68 (s, 1H, 55CH),
6.89–8.04 (m, 9H, Ar-H). MS: m/z, 290 (Mþ). IR (KBr, n, cm21): 1732
(C55O), 1611, 1496 (C55N). Anal. Calcd. for C17H10N2O3: C, 70.34; H,
3.47; N, 9.65. Found: C, 70.22; H, 3.56; N, 9.71.
1
1b. White solid. H NMR (CDCl3, 200 MHz) d 8.72 (s, 1H, 55CH),
7.05–8.19 (m, 8H, Ar-H). MS: m/z, 324 (Mþ). IR (KBr, n, cm21): 1749
(C55O), 1619, 1508 (C55N). Anal. Calcd. for C17H9ClN2O3: C, 62.88; H,
2.79; N, 8.63. Found: C, 62.96; H, 2.70; N, 8.75.
1c. White solid. 1H NMR (CDCl3, 200 MHz) d 8.73 (s, 1H,55CH), 7.04–
8.20 (m, 8H, Ar-H). MS: m/z, 324 (Mþ). IR (KBr, n, cm21): 1749 (C55O),
1618, 1509 (C55N). Anal. Calcd. for C17H9ClN2O3: C, 62.88; H, 2.79; N,
8.63. Found: C, 62.79; H, 2.75; N, 8.56.
1
1d. White solid. H NMR (CDCl3, 200 MHz) d 8.76 (s, 1H, 55CH),
7.10–8.29 (m, 8H, Ar-H). MS: m/z, 335 (Mþ). IR (KBr, n, cm21): 1758
(C55O), 1626, 1516 (C55N). Anal. Calcd. for C17H9N3O5: C, 60.90; H,
2.71; N, 12.53. Found: C, 60.81; H, 2.67; N, 12.64.
1e. White solid. 1H NMR (CDCl3, 200 MHz) d 8.78 (s, 1H,55CH), 7.11–
8.30 (m, 8H, Ar-H). MS: m/z, 335 (Mþ). IR (KBr, n, cm21): 1759 (C55O),
1628, 1517 (C55N). Anal. Calcd. for C17H9N3O5: C, 60.90; H, 2.71; N,
12.53. Found: C, 60.99; H, 2.65; N, 12.45.
1f. White solid. 1H NMR (CDCl3, 200 MHz) d 8.70 (s, 1H,55CH), 7.02–
8.15 (m, 8H, Ar-H), 3.91 (s, 3H, OCH3). MS: m/z, 320 (Mþ). IR (KBr, n,