Paper
One-pot synthesis of 3-hydroxyquinolin-2(1H)-ones from N-phenylacetoacetamide via PhI(OCOCF3)2-mediated α-hydroxylation and H2SO4-promoted intramolecular cyclization.
Published May 20, 2013 · Yucheng Yuan, Rui Yang, D. Zhang-Negrerie
The Journal of organic chemistry
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Abstract
A clean, one-pot synthesis of the biologically important 3-hydroxyquinolin-2(1H)-one compounds has been realized from the readily available N-phenylacetoacetamide derivatives through a PhI(OCOCF3)2-mediated α-hydroxylation and a H2SO4-promoted intramolecular condensation. The hydroxyl group in the generated α-hydroxylated intermediate can be well tolerated in the second H2SO4-promoted cyclization step.
This one-pot synthesis of 3-hydroxyquinolin-2(1H)-ones from N-phenylacetoacetamide provides a cost-effective, environmentally friendly, and sustainable method for producing biologically important compounds.
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