o-Vanillin → 3-(2,6-Dimethoxy-phenyl)-2-[(E)-2-(2-hydroxy-3-methoxy-phenyl)-vinyl]-3H-quinazolin-4-one

Participants

Reaction Steps

A mixture of 80 (170 mg, 0.57 mmol) and 2-hydroxy-3-methoxybenzaldehyde (9, 87 mg, 0.57 mmol) in AcOH (˜5 mL) was refluxed under N2 for 4 days and the reaction was monitored by MS and TLC. Additional 2-hydroxy-3-methoxybenzaldehyde (87 mg, 0.57 mmol) was added and the reaction mixture was refluxed for another 2 days. The solution was concentrated in vacuo and the crude product was purified by flash chromatography on silica gel eluting with EtOAc/hexanes to give the pure 81 as a yellow solid (98 mg, 40%). MS (APCI): m/z 431 (100%, [M+H]+).

Provenance & Evidence