Diastereoselective synthesis of methanopyridoxazocinones

Siva S. Panda; Peter J. Steel

doi:10.1055/s-0034-1379182

Diastereoselective synthesis of methanopyridoxazocinones

Siva S. Panda, Peter J. Steel

Chemistry and Physics

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

Two approaches to the synthesis of oxygen-bridged tetrahydropyridones have been developed. In the first approach, substituted pyrido[4,3-g][1,3]oxazocines derivatives were prepared by diastereoselective one-pot reactions of substituted 7-azacoumarins with enolizable ketones and non-bulky primary amines. In the second one, 3-amido-7-azacoumarins were reacted with enolizable ketones in the presence of a base to form diastereomerically pure pyrido[4,3-g][1,3]oxazocines.

Original language	English (US)
Article number	st-2014-s0510-1
Pages (from-to)	2654-2660
Number of pages	7
Journal	Synlett
Volume	25
Issue number	18
DOIs	https://doi.org/10.1055/s-0034-1379182
State	Published - Oct 7 2014

Keywords

azacoumarin
bridged heterocycles
chirality
diastereomer
synthesis

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-0034-1379182

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title = "Diastereoselective synthesis of methanopyridoxazocinones",

abstract = "Two approaches to the synthesis of oxygen-bridged tetrahydropyridones have been developed. In the first approach, substituted pyrido[4,3-g][1,3]oxazocines derivatives were prepared by diastereoselective one-pot reactions of substituted 7-azacoumarins with enolizable ketones and non-bulky primary amines. In the second one, 3-amido-7-azacoumarins were reacted with enolizable ketones in the presence of a base to form diastereomerically pure pyrido[4,3-g][1,3]oxazocines.",

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T1 - Diastereoselective synthesis of methanopyridoxazocinones

AU - Panda, Siva S.

AU - Steel, Peter J.

N1 - Publisher Copyright: © Georg Thieme Verlag Stuttgart - New York.

PY - 2014/10/7

Y1 - 2014/10/7

N2 - Two approaches to the synthesis of oxygen-bridged tetrahydropyridones have been developed. In the first approach, substituted pyrido[4,3-g][1,3]oxazocines derivatives were prepared by diastereoselective one-pot reactions of substituted 7-azacoumarins with enolizable ketones and non-bulky primary amines. In the second one, 3-amido-7-azacoumarins were reacted with enolizable ketones in the presence of a base to form diastereomerically pure pyrido[4,3-g][1,3]oxazocines.

AB - Two approaches to the synthesis of oxygen-bridged tetrahydropyridones have been developed. In the first approach, substituted pyrido[4,3-g][1,3]oxazocines derivatives were prepared by diastereoselective one-pot reactions of substituted 7-azacoumarins with enolizable ketones and non-bulky primary amines. In the second one, 3-amido-7-azacoumarins were reacted with enolizable ketones in the presence of a base to form diastereomerically pure pyrido[4,3-g][1,3]oxazocines.

KW - azacoumarin

KW - bridged heterocycles

KW - chirality

KW - diastereomer

KW - synthesis

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Diastereoselective synthesis of methanopyridoxazocinones

Abstract

Keywords

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