Ultrasound-Assisted Wittig Reaction for the Synthesis of 3-Substituted 4-Chloroquinolines and Quinolin-4(1H)-ones with Extended π-Conjugated Systems. (5th December 2022)

• Record Type: Journal Article
• Authors: Frites, Wahiba; Khalfaoui, Massaab; Hammal, Lamouri; Silva, Vera L. M.; Silva, Artur M. S.
• Other Names: Pasini Dario Academic Editor.
• Is Part Of: Journal of chemistry. Volume 2022(2022)
• Publication Date: 2022-12-05
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1155/2022/4807767
• Languages: English
• ISSNs: 2090-9063

Abstract

Abstract : 3-(Vinyl-/buta-1, 3-dien-1-yl/4-phenylbuta-1, 3-dien-1-yl)-4-chloro quinolines and quinolin-4(1 H )-ones were synthesized by ultrasound-assisted Wittig reaction of the corresponding 4-chloro-3-formylquinoline and 3-formylquinolin-4(1 H )-ones with nonstabilized ylides. Ease execution, mild conditions, and high yields make this method exploitable for the generation of libraries of 3-substituted 4-chloroquinolines and quinolin-4(1 H )-ones with extended π -conjugated systems. To demonstrate the usefulness of these compounds as precursors for the synthesis of more complex structures, 3-vinylquinolin-4(1 H )-ones were used as dienes in the Diels–Alder reaction with N -methylmaleimide to produce novel acridone derivatives. The attempted Diels–Alder reaction with 3-(buta-1, 3-dien-1-yl)quinolin-4(1 H )-one did not afford the expected cycloadduct; instead, 2-methyl-2 H -pyrano[3, 2- c ]quinoline was obtained. The structures and stereochemistry of the new compounds were established by NMR studies.