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9557947 
Journal Article 
Switchable solvent-controlled divergent synthesis: an efficient and regioselective approach to pyrimidine and dibenzo[b,f][1,4]oxazepine derivatives (Electronic supplementary information (ESI) available: Experimental procedure and characterization of synthesized compounds (1H, 13C and 19F NMR spectra. See DOI: 10.1039/c9qo01126a) 
Jin-Peng, M; Wan-Wan, W; Ying-Lu, C; Bera, S; Wu, J 
2020 
7 
2 
267-272 
English 
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. 
Chemistry--Organic Chemistry; Solvents; Dimethyl sulfoxide; Substrates; Substitutes; Regioselectivity; Pyrimidines; Materials selection; Reaction mechanisms; Nuclear magnetic resonance--NMR; Synthesis; Derivatives; Selectivity