期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 80, 期 15, 页码 7757-7763出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01044
关键词
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资金
- Project of Operational Program Research and Development for Innovations from the Ministry of Education and Sports of Czech Republic [CZ.1.07/2.4.00/31.0130]
- internal faculty project IGA [IGA_PrF_2015_007]
The SNAr reaction of 2,4-dichloropyrimidines, further substituted with an electron-withdrawing substituent at C-S, has selectivity for substitution at C-4. Here we report that tertiary amine nudeophiles show excellent C-2 selectivity. In situ N-dealkylation of an intermediate gives the product that formally corresponds to the reaction of a secondary amine nucleophile at C-2. This reaction is practical (fast under simple reaction conditions, with good generality for tertiary amine structure and moderate to excellent yields) and significantly expands access to pyrimidine structures.
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