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Photochemical Reactions of Tetrahydroquinoxalin-2(1H)-ones and Related Compound

✍ Scribed by Takehiko Nishio; Masaji Kondo; Yoshimori Omote

Publisher
John Wiley and Sons
Year
1991
Tongue
German
Weight
455 KB
Volume
74
Category
Article
ISSN
0018-019X

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✦ Synopsis

Photochemical behaviors of the pyrazinone derivatives 5,6,7,8-tetrahydroquinoxalin-2( 1H)-ones la-c and 1,5,6,7,8,9-hexahydro-2H-cyclohepta[b]pyr~in-2-one Id were investigated. Dye-sensitized photo-oxygenation of la+ 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 H,O, whereas Id gave 3,9a-epidioxy-l,3,5,6,7,8,9,9a-octahydro-2~-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 l a 4 with singlet oxygen. Irradiation of la-b in the presence of alkenes gave tricyclic azetidine derivatives 9 by [2 + 21 cycloaddition of the C=N bond of 1 to the alkene.

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