Synthesis of 1H-pyrrolo[3,2-c]quinoline derivatives via palladium-catalyzed heteroannulation of 2-aryl-3-iodo-4-(phenylamino)quinolines and 4-(N,N-allylphenylamino)-2-aryl-3-iodoquinolines |
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| Authors: | Malose J. Mphahlele Lehlohonolo G. Lesenyeho Hlamulo R. Makelane |
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| Affiliation: | Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, PO Box 392, Pretoria 0003, South Africa |
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| Abstract: | Palladium(0)/copper iodide catalyzed Sonogashira cross-coupling of 2-aryl-3-iodo-4-(phenylamino)quinolines with terminal alkynes afforded series of 1,2,4-trisubstituted 1H-pyrrolo[3,2-c]quinolines in a single-step operation. Conversely, the 4-(N,N-allylphenylamino)-2-aryl-3-iodoquinoline derivatives were found to undergo PdCl2(PPh3)2/CuI catalyzed intramolecular Heck reaction to yield the corresponding 1,3,4-trisubstituted 1H-pyrrolo[3,2-c]quinolines. |
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| Keywords: | 2-Aryl-3-iodo-4-(phenylamino)quinolines 4-(N,N-Allylphenylamino)-2-aryl-3-iodoquinolines Sonogashira reaction Intramolecular Heck reaction 1H-Pyrrolo[3,2-c]quinolines |
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