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2005
Indole derivatives
R 0140
Synthesis of Indolones via Radical Cyclization of N-(2-Halogenoalkanoyl)-SubstiAnilines. — Radical-induced cyclization of title N-halogenoalkanoylanilines (I)
24- 112 tuted
is achieved under the action of systems Bu3SnH—AIBN or Ni powder—iPrOH to afford polysubstituted indolones (II) in moderate to good yields. Main side reaction is the
dehalogenation to give products (III), the product ratio depends on the substitution pattern. The reaction of ortho-substituted anilines (If) and (Ih) gives elimination products
(IV) in the system Ni—iPrOH. N-unsubstituted substrates (V) as well as homologous
amides (VII) do not undergo cyclization reaction (except (VIIb)). — (NISHIO*, T.;
ISEKI, K.; ARAKI, N.; MIYAZAKI, T.; Helv. Chim. Acta 88 (2005) 1, 35-41; Dep.
Chem., Univ. Tsukuba, Tsukuba, Ibaraki 305, Japan; Eng.) — Mischke
2005
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