3.3- Diaryl oxindoles

Diaryl oxindoles are known to exhibit a wide range of biological activities such as antibacterial, antiprotozoal, and anti-inflammatory behavior [61-63]. Generally,... 

In the diaryl amine series 191 (Scheme 47), additional, synthetically valuable, anionic pathways provide routes to anthranilates 190, oxindoles 192, and dibenzazepinones 194. Although not explored in terms of its scope [75c], the lateral metalation-cydization, 191 -> 192, is extensively precedented [69] but harbors intriguing potential for subsequent DreM chemistry. The rearrangement 191 —> 190 is an N —> ortho C anionic Fries equivalent of the aryl O-carbamate migration (Scheme 3E) [75c] and after N-methylation, 190 may be transformed into 1,2,3-trisubstituted systems 193 [76]. In another appealing manifestation of CIPE, the efficient conversion of 191 into dibenzazepinone 194 has been applied in an effective synthesis of the antiepileptic drug oxcarbazepine (Trileptal ) 195 [77] and may also be... 

Using a similar approach, a mild and efficient visible Ught-mediated diarylation of V-substituted V-phenylacrylamides 93 with ArN +X 94 was developed to afford 3,3-disubstituted oxindoles 95 by constructing two C—C bonds in one step via an into-intramolecular sequence (Eq. 9.17) [66]. 

Synthesis of 3,3-disubstituted oxindoles from arylation- and vinylation-carbocycUzation of electron-deficient alkenes with diaryliodonium salts catalyzed by CuCl catalyst was reported by Zhou, Li, and coworkers. A wide range of diaryl and vinyl(aryl)iodonium triflates and various substitutions on phenylacrylamides are compatible for this reaction. Both ( )-physostigmine and ( )-physovenine have been synthesized successfully in 41 and 36% overall yield using this vinyl addition/cyclization method [71]. Fu and coworkers developed a Cul-catalyzed synthesis of oxindole derivatives from readily available Af-alkyl-Af-phenylacrylamides and diaryliodonium triflates [72] (Scheme 8.34). 

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