Convenient Multicomponent One‐Pot Synthesis of 2‐Iminothiazolines and 2‐Aminothiazoles Using Elemental Sulfur Under Aqueous Conditions

Herein, we present a novel one‐pot aqueous reaction for the synthesis of 2‐iminothiazolines and 2‐aminothiazoles using isocyanides, amines, sulfur, and 2′‐bromoacetophenones. The three‐component preparation of thioureas is followed by the one‐pot cyclization leading to the heterocyclic product. This...

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Bibliographic Details
Published in:European journal of organic chemistry 2021-07, Vol.2021 (25), p.3587-3597
Main Authors: Németh, András Gy, Marlok, Bence, Domján, Attila, Gao, Qinghe, Han, Xinya, Keserű, György M., Ábrányi‐Balogh, Péter
Format: Article
Language:English
Subjects:
2-Aminothiazole
2-Iminothiazoline
Amines
Aqueous polysulfide solution
Chemical synthesis
Multicomponent reactions
Sulfur
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Summary:Herein, we present a novel one‐pot aqueous reaction for the synthesis of 2‐iminothiazolines and 2‐aminothiazoles using isocyanides, amines, sulfur, and 2′‐bromoacetophenones. The three‐component preparation of thioureas is followed by the one‐pot cyclization leading to the heterocyclic product. This efficient and mild procedure features excellent step‐ and atom‐economy and enables the chromatography‐free preparation of diversely substituted 2‐iminothiazoline and 2‐aminothiazole derivatives. A multicomponent one‐pot process led to the formation of diversely trisubstituted 2‐iminothiazolines and disubstituted 2‐aminothiazoles under aqueous conditions. Starting from isocyanides, amines, 2’‐bromoacetophenones, and aqueous polysulfide solution or sulfur powder, this efficient procedure enabled the chromatography‐free separation of solid products.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202100548