Chemoselective Cu-catalyzed synthesis of diverse N-arylindole carboxamides, beta-oxo amides and N-arylindole-3-carbonitriles using diaryliodonium salts
- Authors
- Mehra, Manish Kumar; Malik, Monika; Kumar, Bintu; Kumar, Dalip
- Issue Date
- Feb-2021
- Publisher
- ROYAL SOC CHEMISTRY
- Citation
- ORGANIC & BIOMOLECULAR CHEMISTRY, v.19, no.5, pp.1109 - 1114
- Journal Title
- ORGANIC & BIOMOLECULAR CHEMISTRY
- Volume
- 19
- Number
- 5
- Start Page
- 1109
- End Page
- 1114
- URI
- https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/84574
- DOI
- 10.1039/d0ob02247k
- ISSN
- 1477-0520
- Abstract
- Chemoselective copper-catalyzed synthesis of diverse N-arylindole-3-carboxamides, beta-oxo amides and N-arylindole-3-carbonitriles from readily accessible indole-3-carbonitriles, alpha-cyano ketones and diaryliodonium salts has been developed. Diverse N-arylindole-3-carboxamides and beta-oxo amides were successfully achieved in high yields under copper-catalyzed neutral reaction conditions, and the addition of an organic base (DIPEA) resulted in a completely different selectivity pattern to produce N-arylindole-3-carbonitriles. Moreover, the importance of the developed methodology was realized by the synthesis of indoloquinolones and N-((1H-indol-3-yl)methyl)aniline and by a single-step gram-scale synthesis of the naturally occurring cephalandole A analogue.
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