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Molecules 2018, 23(4), 976; https://doi.org/10.3390/molecules23040976

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.
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)
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Abstract

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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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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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