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An unexpected rearrangement of pyrazolium halides based on NN bond cleavage: synthesis of 1,2-dihydropyrimidines

The rearrangement of pyrazolium halides was observed, giving 1,2-dihydropyrimidines in good to high yields. A broad scope of pyrazolium halides bearing various N -substituted benzyls or alkyls can be utilized. A mechanistic study using isotope labelling experiments suggested that the present rearran... Full description

Journal Title: Chemical Communications 2017, Vol.53(50), pp.6792-6795
Main Author: Chen, Qian
Other Authors: Liu, Xiaoshuang , Guo, Fang , Chen, Zhonglin
Format: Electronic Article Electronic Article
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ID: ISSN: 1359-7345 ; E-ISSN: 1364-548X ; DOI: 10.1039/c7cc02525d
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recordid: rscc7cc02525d
title: An unexpected rearrangement of pyrazolium halides based on NN bond cleavage: synthesis of 1,2-dihydropyrimidines
format: Article
creator:
  • Chen, Qian
  • Liu, Xiaoshuang
  • Guo, Fang
  • Chen, Zhonglin
subjects:
  • Labelling
  • Isotopes
  • Formations
  • Chemical Bonds
  • Bearing
  • Synthesis
  • Halides
  • Cleavage
  • Miscellaneous Sciences (So)
  • Chemical and Electrochemical Properties (MD)
  • Chemical and Electrochemical Properties (Ep)
  • Chemical and Electrochemical Properties (Ed)
  • Chemical and Electrochemical Properties (EC)
ispartof: Chemical Communications, 2017, Vol.53(50), pp.6792-6795
description: The rearrangement of pyrazolium halides was observed, giving 1,2-dihydropyrimidines in good to high yields. A broad scope of pyrazolium halides bearing various N -substituted benzyls or alkyls can be utilized. A mechanistic study using isotope labelling experiments suggested that the present rearrangement proceeds through an ylide formation/ring cleavage/ring closure pathway to yield the observed product.
language:
source:
identifier: ISSN: 1359-7345 ; E-ISSN: 1364-548X ; DOI: 10.1039/c7cc02525d
fulltext: fulltext
issn:
  • 1359-7345
  • 1364-548X
  • 1364548X
  • 13597345
url: Link


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titleAn unexpected rearrangement of pyrazolium halides based on NN bond cleavage: synthesis of 1,2-dihydropyrimidines
creatorChen, Qian ; Liu, Xiaoshuang ; Guo, Fang ; Chen, Zhonglin
ispartofChemical Communications, 2017, Vol.53(50), pp.6792-6795
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descriptionThe rearrangement of pyrazolium halides was observed, giving 1,2-dihydropyrimidines in good to high yields. A broad scope of pyrazolium halides bearing various N -substituted benzyls or alkyls can be utilized. A mechanistic study using isotope labelling experiments suggested that the present rearrangement proceeds through an ylide formation/ring cleavage/ring closure pathway to yield the observed product.
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subjectLabelling ; Isotopes ; Formations ; Chemical Bonds ; Bearing ; Synthesis ; Halides ; Cleavage ; Miscellaneous Sciences (So) ; Chemical and Electrochemical Properties (MD) ; Chemical and Electrochemical Properties (Ep) ; Chemical and Electrochemical Properties (Ed) ; Chemical and Electrochemical Properties (EC);
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titleAn unexpected rearrangement of pyrazolium halides based on NN bond cleavage: synthesis of 1,2-dihydropyrimidines
descriptionThe rearrangement of pyrazolium halides was observed, giving 1,2-dihydropyrimidines in good to high yields. A broad scope of pyrazolium halides bearing various N -substituted benzyls or alkyls can be utilized. A mechanistic study using isotope labelling experiments suggested that the present rearrangement proceeds through an ylide formation/ring cleavage/ring closure pathway to yield the observed product.
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titleAn unexpected rearrangement of pyrazolium halides based on NN bond cleavage: synthesis of 1,2-dihydropyrimidines
authorChen, Qian ; Liu, Xiaoshuang ; Guo, Fang ; Chen, Zhonglin
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abstractThe rearrangement of pyrazolium halides was observed, giving 1,2-dihydropyrimidines in good to high yields. A broad scope of pyrazolium halides bearing various N -substituted benzyls or alkyls can be utilized. A mechanistic study using isotope labelling experiments suggested that the present rearrangement proceeds through an ylide formation/ring cleavage/ring closure pathway to yield the observed product.
doi10.1039/c7cc02525d
pages6792-6795
date2017-06-20