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Synlett 2014; 25(18): 2654-2660
DOI: 10.1055/s-0034-1379182
letter
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Synthesis of Methanopyridoxazocinones

Oleksandr S. Detistov
a   Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA
,
Siva S. Panda*
a   Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA
,
Peter J. Steel
b   Chemistry Department, University of Canterbury, Christchurch 8140, New Zealand
,
Abdullah M. Asiri
c   Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi Arabia
d   Center of Excellence for Advanced Material Research, King Abdulaziz University, Jeddah 21589, Saudi Arabia   Fax: +1(352)3929199   eMail: sspanda12@gmail.com   eMail: charlesdennishall@gmail.com
,
C. Dennis Hall*
a   Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA
,
Alan R. Katritzky ,†
a   Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA
c   Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi Arabia
› Institutsangaben
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Publikationsverlauf

Received: 12. Juni 2014

Accepted after revision: 29. August 2014

Publikationsdatum:
07. Oktober 2014 (online)

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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.

Key words

azacoumarin - diastereomer - chirality - bridged heterocycles - synthesis

Supporting Information

    for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
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