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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 45, 2015 - Issue 24
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Original Articles

Facile Synthesis of 4-Oxo-4H-quinolizine-2-carboxamide Derivatives

, , , , &
Pages 2861-2868 | Received 19 Aug 2015, Published online: 14 Dec 2015
 

Abstract

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, 1H NMR and 13C 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.

GRAPHICAL ABSTRACT

SUPPLEMENTAL MATERIAL

Full experimental detail, 1H and 13C NMR spectra, IR, and MS data for this article can be accessed on the publisher’s website.

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