期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 363, 期 21, 页码 4876-4882出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202100793
关键词
Peroxyoxindole; Indium (III) Chloride; C-H functionalization; Trisindoline; Hock cleavage
资金
- SERB, India [CRG/2018/003935]
- DST
- UGC
- SERB
- IISER-Pune
Indium catalyzes sequential remote C-H functionalization and C3-indolylation of peroxyoxindole, leading to the synthesis of terindolinone derivatives. In contrast, FeCl3 ·6H2O facilitates oxidative cleavage of peroxyoxindole and its reaction with indole to afford biologically important trisindoline derivatives. A plausible mechanism for these reactions has been proposed with experimental evidence.
Indium-catalyzed sequential remote C-H functionalization (C-6 position) and C3-indolylation of peroxyoxindole using indole is described for the synthesis of terindolinone derivatives. Whereas, N-substituted 3-phenyl peroxyoxindole derivatives undergoes consecutive skeletal rearrangement to generate transient carbocation, which has been trapped with indole nucleophile to generate 2-(1H-indol-3-yl)-4-alkyl-benzo[b][1,4]oxazin-3(4H)-one derivatives. In contrast with Indium (III) Chloride, FeCl3 . 6H(2)O facilitates oxidative cleavage of the peroxyoxindole (Hock cleavage) and further reaction with indole to afford biologically important trisindoline derivatives. A plausible mechanism has been proposed for these reactions with experimental evidences.
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