3-Hydroxythiazole and 1-Hydroxyimidazole as Products of a Mutual Ring Closure Reaction. Extension to Selenium Derivatives.
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F05%3A00014317" target="_blank" >RIV/00216224:14310/05:00014317 - isvavai.cz</a>
Result on the web
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DOI - Digital Object Identifier
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Alternative languages
Result language
angličtina
Original language name
3-Hydroxythiazole and 1-Hydroxyimidazole as Products of a Mutual Ring Closure Reaction. Extension to Selenium Derivatives.
Original language description
A thiazole derivative can be easily prepared, e.g., from an alpha-thiocyanatoketone and a nitrogen nucleophile. In this work, alpha-bromopropiophenone was chosen as a starting compound. Since the carbonyl group facilitates nucleophilic substitution, bromine can be simply replaced with the thiocyanato group. The following reaction with hydroxylamine hydrochloride provides an intermediate, which undergoes a ring closure reaction. Finally, 3-hydroxy-5-methyl-4-phenylthiazol-2(3H)-iminium chloride or 1-hydroxy-4-methyl-5-phenyl-1,3-dihydro-2H-imidazole-2-thione arises depending on the presence of a base. In the next part, this interesting phenomenon was successfully investigated on selenium derivatives as well. All prepared substances have not been described in the literature yet.
Czech name
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Czech description
Deriváty thiazolu lze snadno připravit např. reakcí alpha-thiokyanátoketonů s dusíkatými nukleofily. V této práci byl jako výchozí sloučenina zvolen alpha-brompropiofenon, neboť karbonylová skupina usnadňuje nukleofilní substituci a brom tak může být snadno nahrazen thiokyanátovou skupinou. Následující reakce s hydroxylaminem hydrochloridem vede k meziproduktu podléhajícímu cyklizaci. V závislosti na přítomnosti báze vzniká 4-fenyl-3-hydroxy-5-methylthiazol-2(3H)-iminium chlorid nebo 5-fenyl-1-hydroxy-4-methyl-1,3-dihydro-2H-imidazol-2-thion. V další části byl tento zajímavý poznatek úspěšně studován rovněž na derivátech selenu. Všechny připravené sloučeniny nebyly dosud popsány v literatuře.
Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
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Continuities
Z - Vyzkumny zamer (s odkazem do CEZ)
Others
Publication year
2005
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Phosphorus, Sulfur, and Silicon and the Related Elements
ISSN
1042-6507
e-ISSN
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Volume of the periodical
180
Issue of the periodical within the volume
7
Country of publishing house
US - UNITED STATES
Number of pages
8
Pages from-to
1683-1690
UT code for WoS article
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EID of the result in the Scopus database
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