期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 87, 期 2, 页码 1032-1042出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c02329
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资金
- Universita degli Studi dell'Insubria
- Universita degli Studi di Milano
A novel synthetic strategy for the direct synthesis of oxazolo-phenoxazine compounds has been achieved through a dimerization/cyclization reaction of 2-benzylamino-phenols. Regioselective formation of 1-benzyl-2-phenyl-6-(aryl-benzyl)amino-benzimidazoles has also been demonstrated using specific starting substrates. The fluorescence emission properties of the synthesized products have been evaluated.
A dimerization/cyclization reaction of 2-benzylamino-phenols for the direct synthesis of the oxazolo-phenoxazine skeleton is reported. The reaction occurs under copper catalysis in the presence of hypervalent iodine(III), giving selectively the 5H-oxazolo[4,5-b]phenoxazine compounds. The cascade process, which allows the conversion of the substrates into the tetracyclic products, involves three C-H functionalization steps. Initial oxidation of electron-rich arenes by the hypervalent iodine is essential for the dimerization of substrates, whereas the formation of the five-membered rings is promoted by the copper species. 1-Benzyl-2-phenyl-6-(aryl-benzyl)amino-benzimidazoles are regioselectively obtained using N,N & PRIME;-dibenzyl-phenylenediamines as starting substrates. The fluorescence emission properties of these classes of products have been evaluated.
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