Electrochemical versus Anionic Oxygenation of Azathymine Derivatives

摘要

Pymetrozine (1) was converted to hemiaminal 2 in low to moderate yield by trapping its dianion with oxygen followed by reduction with ferrous salts. Pymetrozines 18 and 19 failed to undergo this type of oxygenation. All three pymetrozines were oxidized electrochemically at C5 to methyl hemiaminals 20, 21, and 22, respectively.