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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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
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2-Aminothiazole
2-Iminothiazoline
Amines
Aqueous polysulfide solution
Chemical synthesis
Multicomponent reactions
Sulfur
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cited_by cdi_FETCH-LOGICAL-c3578-7d7cee40eda2caae6dfec590174d3bb0b77b6ea4b8f20adb8a4481c123d0ea543
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container_end_page 3597
container_issue 25
container_start_page 3587
container_title European journal of organic chemistry
container_volume 2021
creator Németh, András Gy
Marlok, Bence
Domján, Attila
Gao, Qinghe
Han, Xinya
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Ábrányi‐Balogh, Péter
description 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.
doi_str_mv 10.1002/ejoc.202100548
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subjects 2-Aminothiazole
2-Iminothiazoline
Amines
Aqueous polysulfide solution
Chemical synthesis
Multicomponent reactions
Sulfur
title Convenient Multicomponent One‐Pot Synthesis of 2‐Iminothiazolines and 2‐Aminothiazoles Using Elemental Sulfur Under Aqueous Conditions
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