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Open AccessArticle

Convenient Synthesis of Thiohydantoins, Imidazole-2-thiones and Imidazo[2,1-b]thiazol-4-iums from Polymer-Supported α-Acylamino Ketones

1
Department of Organic Chemistry, Faculty of Science, Palacký University, 17. Listopadu 12, 771 46 Olomouc, Czech Republic
2
JEOL Ltd., Musashino 3-1-2, Akishima, Tokyo 196-8558, Japan
3
RIKEN Center for Sustainable Resource Science, Hirosawa 2-1, Wako, Saitama 351-0198, Japan
4
Institute of Molecular and Translational Medicine, Faculty of Medicine and Dentistry, Palacký University, Hnevotinska 5, 779 00 Olomouc, Czech Republic
*
Author to whom correspondence should be addressed.
Molecules 2018, 23(4), 976; https://doi.org/10.3390/molecules23040976
Received: 10 April 2018 / Revised: 18 April 2018 / Accepted: 20 April 2018 / Published: 23 April 2018
(This article belongs to the Special Issue Solid Phase Synthesis)
The preparation of 5-methylene-thiohydantoins using solid-phase synthesis is reported in this paper. After sulfonylation of immobilized Ser (t-Bu)-OH with 4-nitrobenzenesulfonyl chloride followed by alkylation with various bromoketones, the 4-Nos group was removed and the resulting polymer-supported α-acylamino ketones reacted with Fmoc-isothiocyanate. Cleavage of the Fmoc protecting group was followed by the spontaneous cyclative cleavage releasing the 5-methylene-thiohydantoin derivatives from the polymer support. Reduction with triethylsilane (TES) yielded the corresponding 5-methyl-thiohydantoins. When Fmoc-isothiocyanate was replaced with alkyl isothiocyanates, the trifluoroacetic acid (TFA) mediated cleavage from the polymer support, which was followed by the cyclization reaction and the imidazo[2,1-b]thiazol-4-iums were obtained. Their conversion in deuterated dimethylsulfoxide led to imidazole-2-thiones. View Full-Text
Keywords: heterocycle; thiohydantoin; imidazole; serine; bromoketone; solid-phase synthesis heterocycle; thiohydantoin; imidazole; serine; bromoketone; solid-phase synthesis
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MDPI and ACS Style

Králová, P.; Maloň, M.; Koshino, H.; Soural, M. Convenient Synthesis of Thiohydantoins, Imidazole-2-thiones and Imidazo[2,1-b]thiazol-4-iums from Polymer-Supported α-Acylamino Ketones. Molecules 2018, 23, 976.

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