N-{2-[3-(3-Formyl-2-oxoquinolin-1(2H)-yl)prop-1-ynyl]phenyl}acetamide

Abstract

The title compound,prop-1-ynyl]phenyl}acetamide was synthesized in high yield by Sonogashira cross coupling of 2-oxo-1-(prop-2-ynyl)-1,2-dihydroquinoline-3-carbaldehyde with N-(2-iodophenyl)acetamide. The structure of the compound was fully characterized by IR, 1 H-NMR, 13 C-NMR, Mass spectral analysis and elemental analysis. Keywords: 2-quinolone; Sonogashira coupling; terminal alkyneThe usefulness of 2-quinolone framework has been well demonstrated in the development of a broad range of pharmacologically active compounds including antibacterial, antiulcer, anti HIV, anti-allergic, anti-inflammatory and antifungal agents [1][2][3][4][5][6][7]. In continuation of our efforts to identify novel small molecules of potential pharmacological interest, we have recently reported the synthesis and PDE4 inhibitory properties of 2-quinolone derivatives [8]. In further continuation of our earlier work, we now report the synthesis of a novel analogue i.e., N-{2-[3-(3-formyl-2-oxoquinolin-1(2H)yl)prop-1-ynyl]phenyl}acetamide. The alkynylation of iodoarenes via C-C bond forming reaction under Pd-Cu catalysis (the Sonogashira coupling) [9] was used in our earlier synthesis [8]. The methodology offered a very convenient, mild and one-step process for the direct coupling of terminal alkynes with iodoarene to provide the desired internal alkynes of medicinal value [10]. We adopted the OPEN ACCESS