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Angew Chem Int Ed Engl. 2018 Sep 24;57(39):12737-12740. doi: 10.1002/anie.201807159. Epub 2018 Aug 31.

Reductive C2-Alkylation of Pyridine and Quinoline N-Oxides Using Wittig Reagents.

Author information

1
School of Pharmacy, Sungkyunkwan University, Suwon, 16419, Republic of Korea.
2
Bio and Drug Discovery Division, Korea Research Institute of Chemical Technology, Daejeon, 34114, Republic of Korea.
3
Department of Medicinal and Pharmaceutical Chemistry, University of Science and Technology, Daejeon, 34113, 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:

Wittig reagents; alkylation; methylation; pyridine N-oxides; regioselectivity

PMID:
30070744
DOI:
10.1002/anie.201807159

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