Photo by homajob from unsplash
N-Heterocyclic carbene-catalyzed formal [4+2] benzannulation of enals with suitably substituted pyrimidine-2,4-diones allowing the mild and facile synthesis of functionalized quinazoline-2,4-diones is presented. This oxidative transformation proceeds via the simultaneous generation… Click to show full abstract
N-Heterocyclic carbene-catalyzed formal [4+2] benzannulation of enals with suitably substituted pyrimidine-2,4-diones allowing the mild and facile synthesis of functionalized quinazoline-2,4-diones is presented. This oxidative transformation proceeds via the simultaneous generation of dienolates and α,β-unsaturated acylazoliums and follows a vinylogous Michael/aldol/β-lactonization/decarboxylation/oxidation sequence to afford quinazoline-2,4-diones, including axially chiral ones with suitable substitutions, in an operationally simple procedure. In addition, substituted coumarins as dienolate precursors afforded benzochromen-6-one derivatives.
Journal Title: Organic letters
Year Published: 2022
Link to full text (if available)
Share on Social Media: Sign Up to like & get
recommendations!