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2005
Quinoline derivatives
R 0410
Photochemistry of N-(2-Acylphenyl)-2-methylprop-2-enamides: Competition
Photocyclization and Long-Range Hydrogen Abstraction. — Irradiation
24- 137 Between
of o-acetyl-substituted anilides exclusively affords the dihydroquinolinones (II) by a
6π-electron cyclization—thermal [1,5]-acyl migration mechanism. In contrast, the reaction of o-benzoyl-substituted analogues (III) gives a mixture of cyclization products
(IV) and open-chain amides (V). In the case of o-amidobenzoate (VI) and p-acylanilides (VIII), a simple 6π-electron cyclization affords the dihydroquinolinones (VII) and
(IX), respectively. — (NISHIO*, T.; TABATA, M.; KOYAMA, H.; SAKAMOTO, M.;
Helv. Chim. Acta 88 (2005) 1, 78-86; Dep. Chem., Univ. Tsukuba, Tsukuba, Ibaraki
305, Japan; Eng.) — Mischke
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