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Cobalt-catalysed, regioselective C-H activation of amides with unsymmetrical 1,3-diynes using 8-aminoquinoline as a bidentate directing group
Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences. (Bioorganic and Biophysical Chemistry Laboratory)
2018 (English)Independent thesis Advanced level (degree of Master (Two Years)), 80 credits / 120 HE creditsStudent thesis
Abstract [en]

A cobalt-catalysed, ortho-directed, C-H activation of 8-aminoquinoline amides for the preparation of functionalised isoquinolones is reported. The C-H activation was performed with the amide derived from 8-aminoquinoline which acts as a bidentate directing group to facilitate the C-H activation at the ortho carbon atom of the amide towards annulation/cyclisation, with unsymmetrical 1,3-diynes. The work presented here is an exploration of the regiochemical outcome of an efficient and a novel route of synthesis that tries to gain a deeper insight into the regioselective preference for C-H activated annulations that result in the formation of a diverse range of alkynylated regioisomeric heterocycles. Of the four possible regioisomers, only one is formed as the major product depending on the stereoelectronic properties of the diyne in combination with the nature of the 8-aminoquinoline amide.

Place, publisher, year, edition, pages
2018.
Keywords [en]
C-H activation, cobalt catalysis, unsymmetrical 1, 3-diynes, 8-aminoquinolines, regioselectivity of alkynes.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:lnu:diva-76594OAI: oai:DiVA.org:lnu-76594DiVA, id: diva2:1229974
Subject / course
Chemistry
Educational program
Chemistry Master Programme, 120 credits
Examiners
Available from: 2018-07-03 Created: 2018-07-02 Last updated: 2018-07-03Bibliographically approved

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Dhillon, Prakriti
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CiteExportLink to record
Permanent link

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Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf