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 |
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Hauptverfasser: | , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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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. |
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ISSN: | 1434-193X 1099-0690 |
DOI: | 10.1002/ejoc.202400940 |