Regio- and stereoselectivity of the 1, 3-dipolar cycloaddition of azomethine ylides to 3-nitro-2(1H)-quinolinone derivatives: A new synthesis of Pyrrolo[3, 4-c] quinolines. (26th January 2023)

• Record Type: Journal Article
• Authors: Molnár, Márk; John, Tamás; Dancsó, András; Nyerges, Miklós
• Is Part Of: Tetrahedron. Volume 131(2023)
• Publication Date: 2023-01-26
• Subjects: Azomethine ylides -- 1, 3-Dipolar cycloaddition -- Quinoline -- Stereoselectivity -- X-ray; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2022.133225
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: 1, 3-Dipolar cycloadditions of different azomethine ylides to 3-nitro-2(1H)-quinolinones were carried out to give 3a-nitro-4-oxo-1, 2, 3, 3a, 5, 9 b -hexahydropyrrolo[3, 4-c]quinoline-4-one derivatives in satisfactory yield, in most cases with excellent stereoselectivity. The structure and stereochemistry of cycloadducts were studied in detail by X-ray and NMR spectroscopy methods. Graphical abstract: Regio- and Stereoselectivity of the 1, 3-Dipolar Cycloaddition of Azomethine Ylides to 3-Nitro-2(1 H )-quinolone Derivatives: A New Synthesis of Pyrrolo[3, 4- c ] quinolines. Image 1