Abstract
AbstractPhotochemical behaviors of the pyrazinone derivatives 5,6,7,8‐tetrahydroquinoxalin‐2(1H)‐ones 1a–c and 1,5,6,7,8,9‐hexahydro‐2H‐cyclohepta[b]pyrazin‐2‐one 1d were investigated. Dye‐sensitized photo‐oxygenation of 1a‐c gave the 1:1 adducts 5a–c of the corresponding 3,8a‐epidioxy‐3,5,6,7,8,8a‐hexahydroquinoxalin‐2(1H)‐one 4 and H2O, whereas 1d gave 3,9a‐epidioxy‐1,3,5,6,7,8,9,9a‐octahydro‐2H‐cyclohepta[b]pyrazin‐2‐one 4d (Scheme 2). The different kind of products was interpreted as being the result of the ring strain and steric hindrance of endoperoxides produced from 1a–d with singlet oxygen. Irradiation of 1a–b in the presence of alkenes gave tricyclic azetidine derivatives 9 by [2 + 2] cycloaddition of the CN bond of 1 to the alkene.
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