Synthesis of Functionalized 2‐Hydrazono‐3‐Thiazolines from 2‐Substituted Oxazoles through a One‐Pot Multicomponent/Rearrangement Process
Abstract 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.
Authors
- Adaı́lton J. Bortoluzzi
- M. Marcus
- Ricardo I. M. Beche
- Renata A. Balaguez
- Thaís Andreia Rossa (ORCID: https://orcid.org/0000-0001-9851-447X)
- Giovana S. Ramos
Institutions
- Universidade Federal de Santa Catarina (BR)
- Polydoro Ernani de São Thiago University Hospital (BR)
Publication Details
- Journal
- European Journal of Organic Chemistry
- Published
- 2024-09-17
- DOI
- https://doi.org/10.1002/ejoc.202400940
- Citations
- 1
- Primary Topic
- Multicomponent Synthesis of Heterocycles
- Type
- article
- Field-Weighted Citation Impact
- 0.25
Funders
- Conselho Nacional de Desenvolvimento Científico e Tecnológico
- Fundação de Amparo à Pesquisa e Inovação do Estado de Santa Catarina