4‐(Dimethylamino)pyridine‐Catalyzed (3+2) Annulation of Pyrazoledione‐Derived Morita–Baylis–Hillman Carbonates with 2‐Arylideneindane‐1,3‐Diones: An Access to Dispirocyclic Compounds
Jianning Liao, Jiaqing Xu, Yongjun Wu, Yuxia Hou, Hongchao Guo
Abstract
Abstract A 4‐(dimethylamino)pyridine‐catalyzed (3+2) annulation of pyrazoledione‐derived Morita–Baylis–Hillman (MBH) carbonates with 2‐arylideneindane‐1,3‐diones has been developed to afford various multifunctional spiropyrazole derivatives in 16–99% yields with 3:2–>20:1 diastereoselectivities. As a type of Lewis‐base receptor, the pyrazoledione‐derived MBH carbonates will function as a key substrate in organocatalyzed annulation reactions for diverse syntheses of pyrazolinone‐containing dispirocyclic compounds. magnified image
Topics & Concepts
AnnulationChemistryPyridineCatalysisLewis acids and basesSubstrate (aquarium)StereochemistryCombinatorial chemistryMedicinal chemistryOrganic chemistryOceanographyGeologySynthesis of heterocyclic compoundsSulfur-Based Synthesis TechniquesAsymmetric Synthesis and Catalysis