Diastereoselective synthesis of methanopyridoxazocinones

Siva S. Panda, Peter J. Steel

Research output: Contribution to journalArticle

3 Citations (Scopus)

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 languageEnglish (US)
Article numberst-2014-s0510-1
Pages (from-to)2654-2660
Number of pages7
JournalSynlett
Volume25
Issue number18
DOIs
StatePublished - Oct 7 2014

Fingerprint

Oxazocines
Ketones
Amines
Oxygen
Derivatives

Keywords

  • azacoumarin
  • bridged heterocycles
  • chirality
  • diastereomer
  • synthesis

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Diastereoselective synthesis of methanopyridoxazocinones. / Panda, Siva S.; Steel, Peter J.

In: Synlett, Vol. 25, No. 18, st-2014-s0510-1, 07.10.2014, p. 2654-2660.

Research output: Contribution to journalArticle

Panda, SS & Steel, PJ 2014, 'Diastereoselective synthesis of methanopyridoxazocinones', Synlett, vol. 25, no. 18, st-2014-s0510-1, pp. 2654-2660. https://doi.org/10.1055/s-0034-1379182
Panda, Siva S. ; Steel, Peter J. / Diastereoselective synthesis of methanopyridoxazocinones. In: Synlett. 2014 ; Vol. 25, No. 18. pp. 2654-2660.
@article{08e25e9dd8e34710bc5649fd9f3ae003,
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.",
keywords = "azacoumarin, bridged heterocycles, chirality, diastereomer, synthesis",
author = "Panda, {Siva S.} and Steel, {Peter J.}",
year = "2014",
month = "10",
day = "7",
doi = "10.1055/s-0034-1379182",
language = "English (US)",
volume = "25",
pages = "2654--2660",
journal = "Synlett",
issn = "0936-5214",
publisher = "Georg Thieme Verlag",
number = "18",

}

TY - JOUR

T1 - Diastereoselective synthesis of methanopyridoxazocinones

AU - Panda, Siva S.

AU - Steel, Peter J.

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

UR - http://www.scopus.com/inward/record.url?scp=84911936714&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84911936714&partnerID=8YFLogxK

U2 - 10.1055/s-0034-1379182

DO - 10.1055/s-0034-1379182

M3 - Article

VL - 25

SP - 2654

EP - 2660

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 18

M1 - st-2014-s0510-1

ER -