Synthesis of Functionalized 2‐Hydrazono‐3‐Thiazolines from 2‐Substituted Oxazoles through a One‐Pot Multicomponent/Rearrangement Process

The serendipitous rearrangement of an oxazole nucleus to a thiazoline ring under mild conditions is described. This transformation was achieved by a multicomponent reaction (MCR) featuring 2‐(bromomethyl)oxazoles, thiosemicarbazide, and a carbonyl compound to provide oxazole‐derived isothiosemicarba...

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Veröffentlicht in:European journal of organic chemistry 2024-11
Hauptverfasser: Ramos, Giovana S., Rossa, Thaís A., Balaguez, Renata A., Beche, Ricardo I. M., Bortoluzzi, Adailton J., Sá, Marcus M.
Format: Artikel
Sprache:eng
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Zusammenfassung:The serendipitous rearrangement of an oxazole nucleus to a thiazoline ring under mild conditions is described. This transformation was achieved by a multicomponent reaction (MCR) featuring 2‐(bromomethyl)oxazoles, thiosemicarbazide, and a carbonyl compound to provide oxazole‐derived isothiosemicarbazones, which undergo oxazole ring‐opening and recyclization to 2‐hydrazono‐3‐thiazolines in a one‐pot procedure. This straightforward route produced highly functionalized thiazolines (34–98 % yield) in a chemo‐ and stereoselective manner.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202400940