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Diversity-oriented synthesis of a library of substituted tetrahydropyrones using oxidative carbon-hydrogen bond activation and click chemistry.

Eighteen (2 RS ,6 RS )-2-(4-methoxyphenyl)-6-(substituted ethyl)dihydro-2 H -pyran-4(3 H )ones were synthesized via a DDQ-mediated oxidative carbon-hydrogen bond activation reaction. Fourteen of these tetrahydropyrans were substituted with triazoles readily assembled via azide-alkyne click-chemistry... Full description

Journal Title: Molecules (Basel Switzerland), May 2, 2011, Vol.16(5), pp.3648-3662
Main Author: Zaware, Nilesh
Other Authors: Laporte, Matthew G , Farid, Ramy , Liu, Lei , Wipf, Peter , Floreancig, Paul E
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: E-ISSN: 1420-3049 ; DOI: 10.3390/molecules16053648
Link: http://search.proquest.com/docview/864965420/?pq-origsite=primo
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title: Diversity-oriented synthesis of a library of substituted tetrahydropyrones using oxidative carbon-hydrogen bond activation and click chemistry.
format: Article
creator:
  • Zaware, Nilesh
  • Laporte, Matthew G
  • Farid, Ramy
  • Liu, Lei
  • Wipf, Peter
  • Floreancig, Paul E
subjects:
  • Click Chemistry–Methods
  • Magnetic Resonance Spectroscopy–Chemical Synthesis
  • Molecular Structure–Chemistry
  • Oxidation-Reduction–Chemistry
  • Pyrans–Chemistry
  • Pyrans
ispartof: Molecules (Basel, Switzerland), May 2, 2011, Vol.16(5), pp.3648-3662
description: Eighteen (2 RS ,6 RS )-2-(4-methoxyphenyl)-6-(substituted ethyl)dihydro-2 H -pyran-4(3 H )ones were synthesized via a DDQ-mediated oxidative carbon-hydrogen bond activation reaction. Fourteen of these tetrahydropyrans were substituted with triazoles readily assembled via azide-alkyne click-chemistry reactions. Examples of a linked benzotriazole and pyrazole motif were also prepared. To complement the structural diversity, the alcohol substrates were obtained from stereoselective reductions of the tetrahydropyrone. This library provides rapid access to structurally diverse non-natural compounds to be screened against a variety of biological targets.
language: eng
source:
identifier: E-ISSN: 1420-3049 ; DOI: 10.3390/molecules16053648
fulltext: fulltext
issn:
  • 14203049
  • 1420-3049
url: Link


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titleDiversity-oriented synthesis of a library of substituted tetrahydropyrones using oxidative carbon-hydrogen bond activation and click chemistry.
creatorZaware, Nilesh ; Laporte, Matthew G ; Farid, Ramy ; Liu, Lei ; Wipf, Peter ; Floreancig, Paul E
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identifierE-ISSN: 1420-3049 ; DOI: 10.3390/molecules16053648
subjectClick Chemistry–Methods ; Magnetic Resonance Spectroscopy–Chemical Synthesis ; Molecular Structure–Chemistry ; Oxidation-Reduction–Chemistry ; Pyrans–Chemistry ; Pyrans
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descriptionEighteen (2 RS ,6 RS )-2-(4-methoxyphenyl)-6-(substituted ethyl)dihydro-2 H -pyran-4(3 H )ones were synthesized via a DDQ-mediated oxidative carbon-hydrogen bond activation reaction. Fourteen of these tetrahydropyrans were substituted with triazoles readily assembled via azide-alkyne click-chemistry reactions. Examples of a linked benzotriazole and pyrazole motif were also prepared. To complement the structural diversity, the alcohol substrates were obtained from stereoselective reductions of the tetrahydropyrone. This library provides rapid access to structurally diverse non-natural compounds to be screened against a variety of biological targets.
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