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.

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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

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article

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

Adaı́lton J. Bortoluzzi, M. Marcus, Ricardo I. M. Beche, Renata A. Balaguez et al.
1 citations
European Journal of Organic Chemistry
Multicomponent Synthesis of Heterocycles
0.25
article

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

Adaı́lton J. Bortoluzzi, M. Marcus, Ricardo I. M. Beche, Renata A. Balaguez, Thaís Andreia Rossa, Giovana S. Ramos
article en
1 citations

Abstract

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.

European Journal of Organic ChemistryVol. 27(48)
Universidade Federal de Santa Catarina (BR), Polydoro Ernani de São Thiago University Hospital (BR)
Conselho Nacional de Desenvolvimento Científico e Tecnológico, Fundação de Amparo à Pesquisa e Inovação do Estado de Santa Catarina
Openalex Percentile: Top 48%
Multicomponent Synthesis of Heterocycles
0.25
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