Cu-Catalyzed Dimerization of Indole Derived Oxime Acetate for Synthesis of Biimidazo[1,2-<i>a</i>]indoles

Persulfate-promoted radical cascade trifluoromethylthiolation and cyclization of 3-alkyl-1-(2-(alkynyl)phenyl)indoles with AgSCF 3 were investigated. This protocol provides a novel route to CF 3 S-substituted indolo[1,2-a]quinoline-7-carbaldehydes and CF 3 S-substituted indolo[1,2-a]quinoline-7-methanone derivatives via the formation of the C−SCF 3 bond and C−C bond and benzylic carbon oxidation in a single step. This reaction can accommodate a broad range of functional groups. The single-crystal Xray diffraction data confirm the chemical structure of the product. A scale-up experiment and radical inhibition experiments were operated in the reaction system. Photophysical properties of some selected 5-((trifluoromethyl)thio)indolo[1,2-a]quinoline-7carbaldehydes were studied by UV−visible and fluorescence spectroscopy.

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Cascade Oxidative Trifluoromethylthiolation and Cyclization of 3-Alkyl-1-(2-(alkynyl)phenyl)indoles

Uppalabat

Hassa

Sawektreeratana

et al. 2023

J. Org. Chem.

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Synthesis of 2H-imidazoles via copper-catalyzed homo/cross-coupling of oxime acetates

Liu,

Chen

et al. 2024

Org. Biomol. Chem.

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Cu-Catalyzed Dimerization of Indole Derived Oxime Acetate for Synthesis of Biimidazo[1,2-a]indoles

Abstract: A copper-mediated cyclization and dimerization of indole derived oxime acetate was developed to generate a series of biimidazo[1,2-a]indole scaffolds with two contiguous stereogenic quaternary carbons in one step.

Cited by 2 publications

References 52 publications

Cascade Oxidative Trifluoromethylthiolation and Cyclization of 3-Alkyl-1-(2-(alkynyl)phenyl)indoles

Cascade Oxidative Trifluoromethylthiolation and Cyclization of 3-Alkyl-1-(2-(alkynyl)phenyl)indoles

Synthesis of 2H-imidazoles via copper-catalyzed homo/cross-coupling of oxime acetates

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Cu-Catalyzed Dimerization of Indole Derived Oxime Acetate for Synthesis of Biimidazo[1,2-a]indoles

Abstract: A copper-mediated cyclization and dimerization of indole derived oxime acetate was developed to generate a series of biimidazo­[1,2-a]­indole scaffolds with two contiguous stereogenic quaternary carbons in one step.

Cited by 2 publications

References 52 publications

Cascade Oxidative Trifluoromethylthiolation and Cyclization of 3-Alkyl-1-(2-(alkynyl)phenyl)indoles

Cascade Oxidative Trifluoromethylthiolation and Cyclization of 3-Alkyl-1-(2-(alkynyl)phenyl)indoles

Synthesis of 2H-imidazoles via copper-catalyzed homo/cross-coupling of oxime acetates

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Product

Resources

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Abstract: A copper-mediated cyclization and dimerization of indole derived oxime acetate was developed to generate a series of biimidazo[1,2-a]indole scaffolds with two contiguous stereogenic quaternary carbons in one step.