Cleavage of 3-Aryl-5,6-dihydro-4H-1,2-oxazines Using Zinc and Aqueous Chelating Ethers: Efficient Methodology for N-O Bond Cleavage

P.      Sunil Kumar; K.      M. Lokanatha Rai

doi:10.2174/157017812801322471

Abstract

A mild and efficient methodology for single pot ring opening of 3-aryl-4H-1,2-oxazines to γ-hydroxy ketones was developed using zinc and aqueous chelating ethers. The ether acts as ligand and co-solvent for the reaction. The ability of zinc ions to form stable complexes with chelating ethers activates the zinc towards reduction. Water is the proton source.

Keywords: γ-hydroxy ketones, aqueous medium, ether, 1, 2-oxazine, Zinc, hydrogenation, amino, pyrrolidines, pyridines, 4-aminoalcohols

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Letters in Organic Chemistry

Title:Cleavage of 3-Aryl-5,6-dihydro-4H-1,2-oxazines Using Zinc and Aqueous Chelating Ethers: Efficient Methodology for N-O Bond Cleavage

Volume: 9 Issue: 6

Author(s): P. Sunil Kumar and K. M. Lokanatha Rai

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Keywords: γ-hydroxy ketones, aqueous medium, ether, 1, 2-oxazine, Zinc, hydrogenation, amino, pyrrolidines, pyridines, 4-aminoalcohols

Abstract: A mild and efficient methodology for single pot ring opening of 3-aryl-4H-1,2-oxazines to γ-hydroxy ketones was developed using zinc and aqueous chelating ethers. The ether acts as ligand and co-solvent for the reaction. The ability of zinc ions to form stable complexes with chelating ethers activates the zinc towards reduction. Water is the proton source.

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Sunil Kumar P. and M. Lokanatha Rai K., Cleavage of 3-Aryl-5,6-dihydro-4H-1,2-oxazines Using Zinc and Aqueous Chelating Ethers: Efficient Methodology for N-O Bond Cleavage, Letters in Organic Chemistry 2012; 9 (6) . https://dx.doi.org/10.2174/157017812801322471