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

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,5,9b-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.