Catalysis-free synthesis of thiazolidine–thiourea ligands for metal coordination (Au and Ag) and preliminary cytotoxic studies

Salvador, Daniel; Herrera, Raquel P.; Gimeno, M. Concepcion

doi:10.1039/d3dt00079f

Cited by 1 publication

(1 citation statement)

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“…Synthetic approaches toward these types of thiazolidines are relatively common in the literature, usually employing isothiocyanate derivatives as reaction partners; , however, thiazolidin-2-imines (or thiazolidin-2-ylideneamines) in which the α-carbon situated between the nitrogen atom of the five-membered ring and the exocyclic CC bond is attached to substituents other than oxygen (carbonyl) or hydrogen (methylenic) have not received an analogous amount of attention. These scaffolds are usually accessed by reacting propargylamines with isothiocyanate derivatives; in most cases, no catalyst is required .…”

Section: Introductionmentioning

confidence: 99%

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

Zorba,

Stylianakis,

Tsoureas

et al. 2024

J. Org. Chem.

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The synthesis of thiazolines, thiazolidines, and thiazolidinones has been extensively studied, due to their biological activity related to neurodegenerative diseases, such as Parkinson's and Alzheimer'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.

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Section: Introductionmentioning

confidence: 99%