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LETTER
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(12) Without triethylamine, the reaction of 1a and 2a gave only
traces of desired compound 4a.
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(14) Anthraquinone 4c; Typical Procedure. To a stirred
solution of 1,4-naphthoquinone 2a (72 mg, 0.46 mmol) and
2-pyrone 1c (50 mg, 0.23 mmol) in toluene (5 mL) was
added Et3N (2 mg, 0.02 mmol) and the reaction mixture was
heated to reflux for 2 h. Then the reaction mixture was
allowed to cool to r.t. After evaporation of the solvent, the
crude product was purified by column chromatography
(hexane–EtOAc, 50:1) to give anthraquinone 4c (70 mg,
93%) as an orange solid; mp 210–212 °C. IR (neat): 1662,
1630, 1591, 1424, 1349, 1285, 1217, 1126, 1017, 747, 708
cm–1. 1H NMR (300 MHz, CDCl3): d = 7.07 (d, J = 8.1 Hz,
1 H), 7.47–7.49 (m, 3 H), 7.57–7.61 (m, 2 H), 7.67 (d,
J = 8.1 Hz, 1 H), 7.80–7.85 (m, 2 H), 8.27–8.34 (m, 2 H),
13.3 (br, 1 H). Anal. Calcd for C20H12O3S: C, 72.27; H, 3.64.
Found: C, 72.48; H, 3.66.
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