Copper-Catalyzed One-Pot Synthesis of Thiazolidin-2-imines

• DOI: 10.1021/acs.joc.4c00394
• Publication Date: 2024-05-10T06:50:35Z
• Authors: Leandros P. Zorba; Ioannis Stylianakis; Nikolaos Tsoureas; Antonios Kolocouris; Georgios C. Vougi...
• Keywords: Reaction conditions; Antiparasitic

The synthesis of thiazolines, thiazolidines, and thiazolidinones has been extensively studied, due to their biological activity related neurodegenerative diseases, such as Parkinson's Alzheimer's, well antiparasitic antihypertensive properties. closely thiazolidin-2-imines have studied less, efficient strategies for synthesizing them, mainly based on the reaction propargylamines with isothiocyanates, explored less. use one-pot approaches, providing modular, straightforward, sustainable access these compounds, also received very little attention. Herein, we report a novel, one-pot, multicomponent, copper-catalyzed among primary amines, ketones, terminal alkynes, toward bearing quaternary carbon centers five-membered ring, in good excellent yields. Density functional theory calculations, combined experimental mechanistic findings, suggest that copper(I)-catalyzed between situ-formed isothiocyanates proceeds lower energy barrier pathway leading S-cyclized product, compared N-cyclized one, chemo- regioselective formation 5-exo-dig thiazolidin-2-imines.