Phenyliodine bis(trifluoroacetate)-mediated oxidative C-C bond formation: synthesis of 3-hydroxy-2-oxindoles and spirooxindoles from anilides.

Autor: Wang J; Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China., Yuan Y, Xiong R, Zhang-Negrerie D, Du Y, Zhao K
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2012 May 04; Vol. 14 (9), pp. 2210-3. Date of Electronic Publication: 2012 Apr 12.
DOI: 10.1021/ol300418h
Abstrakt: The reaction of phenyliodine bis(trifluoroacetate) (PIFA) with a series of anilides 1 (E = CO(2)Et) in CF(3)CH(2)OH was found to give 3-hydroxy-2-oxindole derivatives 2, while that with various anilides 1' (E = CON(R(4))Ar) afforded the C(2)-symmetric or unsymmetric spirooxindoles 3. These processes feature a metal-free oxidative C(sp(2))-C(sp(3)) bond formation, followed by oxidative hydroxylation or spirocyclization.
Databáze: MEDLINE