The interaction between 4-oxothiazolidine-2-ylidene thioamides and iodine: a regioselective two-component 4-oxothiazolidine-2-ylidene thioamide to thiazolo[3,2-c]pyrimidine transformation mediated by iodine
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Abstract
This study investigated the interaction between selected 4-oxothiazolidine-2-ylidene thioamides 2a-c and iodine in acetone. The interaction followed two main reaction pathways: (1) iodine-mediated cyclization resulting in the formation of thiazolopyrimidine 7, and (2) electrophilic iodine attack on the thioamide sulfur atom, producing a complex mixture of iodine adducts. Due to the equilibrium of Z/E isomerization being strongly shifted to the Z-isomer in polar solvents, only the thioamide (E)-2b successfully formed thiazolopyrimidine 7. The other two derivatives, (Z)-2a and (Z)-2c, followed the second reaction pathway. The factors influencing the heterocyclization of (E)-2b and its intermediates were thoroughly examined. This research provides the first description of an iodine-mediated heterocyclization leading to a thiazolopyrimidine scaffold. The literature on iodine-mediated heterocyclization leading to fused pyrimidines is limited, highlighting the significance of this study.
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Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution license 4.0 that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
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Ministarstvo Prosvete, Nauke i Tehnološkog Razvoja
Grant numbers 451-03-66/2024-03/200026
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