4.4 Article

Silyl Cyanopalladate-Catalyzed Friedel-Crafts-Type Cyclization Affording 3-Aryloxindole Derivatives

期刊

SYNLETT
卷 32, 期 9, 页码 935-939

出版社

GEORG THIEME VERLAG KG
DOI: 10.1055/a-1373-7017

关键词

Lewis acid catalysis; Friedel-Crafts reaction; cyclization; oxindoles; S(N)1 reaction

资金

  1. Japan Society for the Promotion of Sciences (JSPS) [19H02706, 19K15548]
  2. Feasibility Study Program of the Frontier Chemistry Center, Faculty of Engineering, Hokkaido University
  3. Grants-in-Aid for Scientific Research [19H02706, 19K15548] Funding Source: KAKEN

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3-Aryloxindole derivatives were synthesized via a Friedel-Crafts-type cyclization, catalyzed by a trimethylsilyl tricyanopalladate complex. Various diethyl phosphates derived from N-arylmandelamides were efficiently converted into oxindoles, with the use of N,N-dibenzylamide leading to a benzo-fused delta-lactam. Substitution reactions on oxindole products yielded 3,3-diaryloxindoles with two different aryl groups.
3-Aryloxindole derivatives were synthesized through a Friedel-Crafts-type cyclization. The reaction was catalyzed by a trimethylsilyl tricyanopalladate complex generated in situ from trimethylsilyl cyanide and Pd(OAc)(2). Wide varieties of diethyl phosphates derived from N-arylmandelamides were converted almost quantitatively into oxindoles. When N,N-dibenzylamide was used instead of an anilide substrate, a benzo-fused delta-lactam was obtained. An oxindole product was subjected to substitution reactions to afford 3,3-diaryloxindoles with two different aryl groups.

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