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Switchable solvent-controlled divergent synthesis: an efficient and regioselective approach to pyrimidine and dibenzo[b,f][1,4]oxazepine derivatives

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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.

Graphical abstract: Switchable solvent-controlled divergent synthesis: an efficient and regioselective approach to pyrimidine and dibenzo[b,f][1,4]oxazepine derivatives

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Publication details

The article was received on 11 Sep 2019, accepted on 19 Nov 2019 and first published on 20 Nov 2019


Article type: Research Article
DOI: 10.1039/C9QO01126A
Org. Chem. Front., 2020, Advance Article

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    Switchable solvent-controlled divergent synthesis: an efficient and regioselective approach to pyrimidine and dibenzo[b,f][1,4]oxazepine derivatives

    J. Meng, W. Wang, Y. Chen, S. Bera and J. Wu, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/C9QO01126A

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