@article {43601,
	title = {Copper-Catalyzed One-Pot Synthesis of Thiazolidin-2-imines},
	journal = {Journal of Organic Chemistry},
	volume = {89},
	year = {2024},
	month = {2024},
	pages = {7727 - 7740},
	publisher = {American Chemical Society},
	abstract = {The synthesis of thiazolines, thiazolidines, and thiazolidinones has been extensively studied, due to their biological activity related to neurodegenerative diseases, such as Parkinson{\textquoteright}s and Alzheimer{\textquoteright}s, as well as their antiparasitic and antihypertensive properties. The closely related thiazolidin-2-imines have been studied less, and efficient strategies for synthesizing them, mainly based on the reaction of propargylamines with isothiocyanates, have been explored less. The use of one-pot approaches, providing modular, straightforward, and sustainable access to these compounds, has also received very little attention. Herein, we report a novel, one-pot, multicomponent, copper-catalyzed reaction among primary amines, ketones, terminal alkynes, and isothiocyanates, toward thiazolidin-2-imines bearing quaternary carbon centers on the five-membered ring, in good to excellent yields. Density functional theory calculations, combined with experimental mechanistic findings, suggest that the copper(I)-catalyzed reaction between the in situ-formed propargylamines and isothiocyanates proceeds with a lower energy barrier in the pathway leading to the S-cyclized product, compared to that of the N-cyclized one, toward the chemo- and regioselective formation of 5-exo-dig S-cyclized thiazolidin-2-imines.},
	author = {Zorba, Leandros P. and Stylianakis, Ioannis and Tsoureas, Nikolaos and Antonios Kolocouris and Georgios C. Vougioukalakis}
}
