Jump to main content
Jump to site search

Issue 20, 2012
Previous Article Next Article

N-Heterocyclic carbene-catalyzed cascade annulation reaction of o-vinylarylaldehydes with nitrosoarenes: one-step assembly of functionalized 2,3-benzoxazin-4-ones

Author affiliations

Abstract

The NHC-catalyzed reactions of ortho electron-deficient vinyl substituted arylaldehydes with nitrosoarenes were studied. The reactions produced multifunctional 2,3-benzoxazin-4-ones in good to excellent yields via a cascade aza-benzoin reaction between aldehyde and nitroso groups followed by an intramolecular oxo-Michael addition. The resulting 1-acetate substituted 2,3-benzoxazinones were transformed into a new type of β-hydroxycarboxylate derivatives or 3-oxo-1-isobenzofuranacetates, respectively, under different reductive conditions. This work not only provides a simple and efficient method for the construction of multifunctional 2,3-benzoxazin-4-ones of potential pharmacological interest, but also expands the application of NHC-catalyzed cascade reactions in the formation of carbon–heteroatom and heteroatom–heteroatom bonds.

Graphical abstract: N-Heterocyclic carbene-catalyzed cascade annulation reaction of o-vinylarylaldehydes with nitrosoarenes: one-step assembly of functionalized 2,3-benzoxazin-4-ones

Back to tab navigation

Supplementary files

Publication details

The article was received on 18 Jan 2012, accepted on 19 Mar 2012 and first published on 21 Mar 2012


Article type: Paper
DOI: 10.1039/C2OB25137J
Org. Biomol. Chem., 2012,10, 4088-4094

  •   Request permissions

    N-Heterocyclic carbene-catalyzed cascade annulation reaction of o-vinylarylaldehydes with nitrosoarenes: one-step assembly of functionalized 2,3-benzoxazin-4-ones

    Z. Sun and Y. Cheng, Org. Biomol. Chem., 2012, 10, 4088
    DOI: 10.1039/C2OB25137J

Search articles by author

Spotlight

Advertisements