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N-Heterocyclic Carbene-Catalyzed Aza-Michael-Mannich-Lactamization Cascade for the Enantioselective Synthesis of Pyrazoloquinolin-3-ones.

Sayan SheeDeeptanu SarkarAkkattu T Biju
Published in: Organic letters (2023)
The enantioselective synthesis of functionalized pyrazoloquinolin-3-ones via N-heterocyclic carbene-catalyzed cascade reaction of α-bromoenals with 2-aminoaryl N -tosyl hydrazones is reported. The in situ-generated α,β-unsaturated acylazoliums underwent an aza-Michael-Mannich-lactamization sequence to afford the tricyclic products bearing three contiguous stereocenters, including a sterically demanding quaternary stereocenter with high enantioselectivity. The unprotected amine-triggered aza-Michael pathway over the competing amidation pathway is noteworthy.
Keyphrases
  • room temperature
  • quantum dots
  • molecularly imprinted
  • mass spectrometry
  • simultaneous determination