3-Hydroxythiazole and 1-Hydroxyimidazole as Products of a Mutual Ring Closure Reaction. Extension to Selenium Derivatives.
| Authors | |
|---|---|
| Year of publication | 2005 |
| Type | Article in Periodical |
| Magazine / Source | Phosphorus, Sulfur, and Silicon and the Related Elements |
| MU Faculty or unit | |
| Citation | |
| Field | Organic chemistry |
| Keywords | Thiazole; imidazole; cyclization; selenium |
| 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. |
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