![(2S)-2-({[(2-Methyl-2-propanyl)oxy]carbonyl}amino)-4-pentynoic acid structure](https://static.chemtradehub.com/structs/630/63039-48-5-b66d.webp "(2S)-2-({[(2-Methyl-2-propanyl)oxy]carbonyl}amino)-4-pentynoic acid structure")
(2S)-2-({[(2-Methyl-2-propanyl)oxy]carbonyl}amino)-4-pentynoic acid
CAS Number:
63039-48-5
Molecular Formula:
C10H15NO4
Switchable solvent-controlled divergent synthesis: an efficient and regioselective approach to pyrimidine and dibenzo[b,f][1,4]oxazepine derivatives
Literature Information
Publication Date
2019-11-20
DOI
10.1039/C9QO01126A
Impact Factor
5.281
Authors
Jin-Peng Meng, Wan-Wan Wang, Ying-Lu Chen, Saurav Bera, Jun Wu
View Original
Abstract
Herein an efficient and regioselective method for the divergent synthesis of pyrimidine and dibenzo[b,f][1,4]oxazepine (DBO) derivatives from the same starting materials was developed. The selectivity can be rationally tuned via the judicious choice of reaction solvents. With 1,4-dioxane used as the solvent, 2-pyrimidinyloxy-N-arylbenzylamines (O-substituted pyrimidines) were obtained in excellent yields, whereas use of dimethyl sulfoxide (DMSO) as solvent afforded N-(2-hydroxybenzyl)-N-phenylpyrimidin-2-amines (N-substituted pyrimidines) in excellent yields, or DBO derivatives in moderate to excellent yields. The easily-accessible substrates and operational simplicity make the process suitable for further exploration. The reaction mechanism involved the SNAr reaction and Smiles rearrangement as key steps.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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