Selenium Dioxide → HCID 25228494, compound

Participants

Reaction Conditions

Reaction Steps

Referring to FIG. 21, compound 13a (304.3 mg, 1.63 mmol) was dissolved in m-xylenes (2 mL) and stirred under a nitrogen atmosphere. Selenium dioxide (272.29 mg 2.45 mmol) was added and the yellow-orange mixture was heated to 90° C. for 4 h. The black reaction mixture was filtered through cotton, washing several times with chloroform. The filtrate was directly adsorbed onto silica gel and purified by column chromatography (EtOAc) to afford 14a (136.4 mg, 0.68 mmol, 42%) as a pale yellow oil: 1H NMR (CDCl3,) δ 10.11 (1H, s), 8.11 (1H, d, J=8.0 Hz), 7.74 (1H, d, J=8.4 Hz), 7.73 (1H, d, J=8.0 Hz), 7.31 (1H, dd, J=9.6, 2.8 Hz), 7.23 (1H, d, J=1.6 Hz), 3.15 (6H, s); 13C NMR (CDCl3,) δ 194.5, 153.0, 151.9, 150.2, 136.9, 128.6, 123.1, 119.1, 113.8, 107.0, 40.7; FTIR (neat) 2920, 1705, 1620, 1537, 1508, 1382, 1255, 1155, 1066, 835, 761 cm−1; MS (ESI) m/z calculated for (C12H12N2O+H)+ 201, found, 201; HRMS (ESI) m/z calculated for (C12H12N2O+H)+ 201.1028, found, 201.1055.

Provenance & Evidence