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Synthesis 2018; 50(08): 1699-1710
DOI: 10.1055/s-0036-1591884
DOI: 10.1055/s-0036-1591884
paper
Substituent Effects of 2-Pyridones on Selective O-Arylation with Diaryliodonium Salts: Synthesis of 2-Aryloxypyridines under Transition-Metal-Free Conditions
Financial support from the ‘Overseas 100 Talents Program’ of Guangxi Higher Education, National Natural Science Foundation of China (21562005, 21602037), State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China (CMEMR2015-A05), and Natural Science Foundation of Guangxi (2015GXNSFCA139001, 2016GXNSFFA380005) are greatly appreciated.Further Information
Publication History
Received: 03 December 2017
Accepted after revision: 08 December 2017
Publication Date:
24 January 2018 (online)
‡ X.-H. Li and A.-H. Ye contributed equally to this work
Abstract
An efficient transition-metal-free strategy to synthesize 2-aryloxypyridine derivatives has been developed by a selective O-arylation of 2-pyridones with diaryliodonium salts. The reaction was compatible with a series of functional groups for 2-pyridones and diaryliodonium salts such as halides, nitro, cyano, and ester groups. The substituents at the C6-position of 2-pyridones favored O-arylation products because of steric hindrance. The reaction was easily performed on a gram-scale and 6-chloro-2-pyridone was a good precursor to access various unsubstituted 2-aryloxypyridines by dehalogenation. A P2Y1 lead compound analogue could be prepared in good yield over two steps.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591884.
- Supporting Information
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For selected examples for modification of 2-aryloxypyridines, see:
For selected examples of N-arylation of 2-pyridones, see:
For selected examples of O-arylation of 2-pyridones, see:
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