Selenium Dioxide → HCID 25228498, compound

Participants

Reaction Conditions

Reaction Steps

Referring now to FIG. 22, under a nitrogen atmosphere, selenium dioxide (67.3 mg, 0.606 mmol) was added to a solution of 17 (99.1 mg, 0.4027 mmol) in xylenes (3 mL). The mixture was heated to 100° C. for 3 h, then filtered hot through cotton, rinsing with chloroform. The product was adsorbed onto silica gel and purified by column chromatography (4:6 EtOAc/hexane) to afford 18 (60 mg, 0.230 mmol, 57%) as a white solid: 1H NMR (CDCl3) δ 10.21 (1H, s), 8.41 (1H, d, J=8.8 Hz), 8.33 (1H, d, J=8.4 Hz), 8.06 (1H, d, J=8.8 Hz), 7.91 (1H, d, J=8.8 Hz), 7.80 (1H, dd, J=1.6, 8.4 Hz) 3.17 (3H, s), 3.07 (3H, s); 13C NMR (CDCl3) δ 193.6, 165.8, 152.9, 147.7, 137.2, 136.8, 135.6, 132.21, 129.9, 127.9, 118.1, 37.0; FTIR (neat) 2922, 2876, 1705, 1661, 1366, 853, 758 cm−1; MS (ESI) m/z calculated for (C13H12N2O2S+H)+ 261, found 261; HRMS (ESI) m/z calculated for (C13H12N2O2S+H)+ 261.0692, found 261.0661.

Provenance & Evidence