An Efficient and Facile Synthesis of 2-Chloro-3-formyl Quinolines from Acetanilides in Micellar Media by Vilsmeier-Haack Cyclisation

Abstract

Acetanilides efficiently undergo Vilsmeier Haack cyclisation in micellar media to afford 2-chloro-3-formyl quinoline derivatives in good yields. This procedure works efficiently in CTAB (cetyl trimethyl ammonium bromide), SDS (sodium dodecyl sulphate) and TX (Triton-X-100) media under reflux conditions particularly from deactivated acetanilides in good yields.

Synthesis and characterization of novel quinoline selenium compounds: X-ray structure of 6-methoxy-3H-[1,2]diselenolo[3,4-b]quinoline

“…Due to their importance as substructures in a broad range of natural and designed products, significant efforts have been directed into the development of new quinoline based structures [6]. Amongst methodologies reported for the preparation of quinolines, Vilsmeier [7] cyclisation is the most straightforward protocol (Scheme 1). Therefore, for the synthesis of 2-chloro-3-formylquinolines in the present reported work, Vilsmeier reagent was prepared and reacted with the corresponding acetanilides.…”

DBU-catalyzed expeditious and facile multicomponent synthesis of N-arylquinolines under microwave irradiation

“…The classical methods for the preparation of quinoline derivatives include the Skraup, Doebner-Von Miller, Conrad-Limbach, Combes, and Pfitzinger syntheses [9][10][11][12][13]. Owing to the remarkable potential of these compounds as a source of valuable drugs, various synthetic methods have also been reported [14][15][16][17][18][19]. Most of these processes, however, suffer from one or other drawbacks such as long reaction times, poor product yields, harsh conditions, high costs, and use of hazardous catalysts.…”

Novel oxazine skeletons as potential antiplasmodial active ingredients: Synthesis, in vitro and in vivo biology of some oxazine entities produced via cyclization of novel chalcone intermediates

“…30,31 All the aromatic ketones were obtained from Sigma-Aldrich. Melting points were determined by open-tube capillaries method and are uncorrected.…”