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Facile Synthesis of 4-Oxo-4H-quinolizine-2-carboxamide Derivatives
Umeå University, Faculty of Science and Technology, Department of Chemistry. Umeå University, Faculty of Medicine, Umeå Centre for Microbial Research (UCMR).
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2015 (English)In: Synthetic Communications, ISSN 0039-7911, E-ISSN 1532-2432, Vol. 45, no 24, 2861-2868 p.Article in journal (Refereed) PublishedText
Abstract [en]

A facile synthetic method for the construction of 2-substituted-4-oxo-4H-quinolizine-based core structure has been successfully developed. The synthesis made use of a one-pot Stobbe condensation followed by cyclization starting from the commercially available 2-pyridinecarbaldehyde. The structure of the formed 4-oxo-4H-quinolizine-2-carboxylate was fully confirmed by mass spectra, H-1 NMR and C-13 NMR, correlation spectrography, heteronuclear multiple bond correlation, and heteronuclear single quantum coherence (HSQC) spectra. The ethyl carboxylate moiety was then further functionalized via direct aminolysis by a range of amines to afford the corresponding 4-oxo-4H-quinolizine-2-carboxamides 4a-i in moderate to good yields.

Place, publisher, year, edition, pages
Taylor & Francis, 2015. Vol. 45, no 24, 2861-2868 p.
Keyword [en]
Carboxamide, 4-oxo-4H-quinolizine, Stobbe condensation
National Category
Organic Chemistry
URN: urn:nbn:se:umu:diva-114392DOI: 10.1080/00397911.2015.1112918ISI: 000366833700009OAI: diva2:895108
Available from: 2016-01-18 Created: 2016-01-18 Last updated: 2016-01-18Bibliographically approved

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Vo, Duy D
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Department of ChemistryUmeå Centre for Microbial Research (UCMR)
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