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Reductive C2‐Alkylation of Pyridine and Quinoline N‐Oxides Using Wittig Reagents |
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| Authors: | Dr Jihye Park Hyunjung Oh Saegun Kim Kyuneun Kim Dr Ashok Kumar Pandey Sang Hoon Han Dr Soo Bong Han Prof Dr In Su Kim |
| Institution: | 1. School of Pharmacy, Sungkyunkwan University, Suwon, Republic of Korea;2. Bio and Drug Discovery Division, Korea Research Institute of Chemical Technology, Daejeon, Republic of Korea;3. Department of Medicinal and Pharmaceutical Chemistry, University of Science and Technology, Daejeon, Republic of Korea |
| Abstract: | The ability to alkylate pyridines and quinolines is important for their further development as pharmaceuticals and agrochemicals, and for other purposes. Herein we describe the unprecedented reductive alkylation of pyridine and quinoline N‐oxides using Wittig reagents. A wide range of pyridine and quinoline N‐oxides were converted into C2‐alkylated pyridines and quinolines with excellent site selectivity and functional‐group compatibility. Sequential C?H functionalization reactions of pyridine and quinoline N‐oxides highlight the utility of the developed method. Detailed labeling experiments were performed to elucidate the mechanism of this process. |
| Keywords: | alkylation methylation pyridine N-oxides regioselectivity Wittig reagents |