Copper Catalyzed [3+2] Annulation Reaction of Exocyclic Sulfonyl Enamides for the Synthesis of N,O‐Spiroketal and Spiroketal

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(44)

Published: June 1, 2024

A copper-catalyzed [3+2] annulation reaction of exocyclic enamines/enol ethers with 1,4-benzoquinone esters has been developed, providing facile access to N,O-spiroketals and spiroketals under mild conditions broad substrate scope (26 examples, 71-94 % yields). Gram scale synthesis chemical transformations demonstrated that this method is potentially useful in the natural products drugs containing a N,O- spiroketal moiety. The chiral N,O-spiroketal could be obtained 98 ee after recrystallization, when SaBOX ligand was employed.

Language: Английский

Silver‐Catalyzed Tandem Reaction of β‐Alkynyl Ketones toward Spiro[isochromene‐1,4′‐quinoline] with Anticancer Activities

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(14), P. 2332 - 2337

Published: June 16, 2023

Abstract Spirocyclic frameworks could enhance the drug‐like properties of planar bioactive molecules by increasing their three‐dimensionality, making development synthetic methodology and bioactivity assays for spiro compounds highly attractive. This work reported silver‐catalyzed tandem cycloisomerization/Povarov reaction between β‐alkynyl ketones hexahydro‐1,3,5‐triazines, access to spiro[isochromene‐1,4’‐quinoline]. protocol was characterized remarkable efficiency, low catalyst‐loading high diastereoselectivity. Moreover, spirocyclic quinolines exhibited good cytotoxicity in U937 cells activating Notch‐signaling pathway exclusively.

Language: Английский