3-Hydroxythiazole and 1-hydroxyimidazole as products of a mutual ring closure reaction: Extension to selenium derivatives

被引:3
作者
Fajkusova, D [1 ]
Pazdera, P [1 ]
机构
[1] Masaryk Univ, Dept Organ Chem, CS-61137 Brno, Czech Republic
关键词
cyclization; imidazole; selenium; thiazole;
D O I
10.1080/104265090885129
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A thiazole derivative can be easily prepared, e.g., front 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 4a or 1-hydroxy-4-methyl-5-phenyl-1,3-dihydro-2H-imidazole-2-thione 5a arises depending on the presence of a base. lit 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.
引用
收藏
页码:1683 / 1689
页数:7
相关论文
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[1]   UBER THIAZOLE .26. DIE SYNTHESE VON 3-SUBSTITUIERTEN THIAZOLON-(2)-IMIDEN AUS ALPHA-RHODANKETONEN [J].
BEYER, H ;
RUHLIG, G .
CHEMISCHE BERICHTE-RECUEIL, 1956, 89 (01) :107-114