Chemical properties of 5-(1,1,2,2-tetrafluoroethoxy)-4-phenylthiazole derivatives

• Published in: Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2015-01, Vol.51 (1), p.80-87
• Main Authors: Davydova, Yulia А., Sokolenko, Taras M., Vlasenko, Yurii G., Yagupolskii, Yurii L.
• Format: Article
• Language: English
• Subjects: Chemistry; Chemistry and Materials Science; Organic Chemistry; Pharmacy
• ISSN: 0009-3122; 1573-8353
• DOI: 10.1007/s10593-015-1663-z

In the present study, the possibility of converting [5-(1,1,2,2-tetrafluoroethoxy)-4-phenylthiazol-2-yl]amine to 2-halothiazoles and an azo compound via diazotation of the amine functionality was demonstrated. It was found that the reaction of [5-(1,1,2,2-tetrafluoroethoxy)-4-phenylthiazol-2-yl]amine with acyl and sulfonyl chlorides leads to products resulting from substitution exclusively at the exocyclic nitrogen atom. The halogen atom at position 2 of thiazole ring is substituted by S-nucleophiles or hydrogen atom upon catalytic hydrogenation on Pd/C. 2-Bromo-5-(1,1,2,2-tetrafluoroethoxy)-4-phenylthiazole was successfully employed in the synthesis of the corresponding α-thiazolylbenzyl alcohol and 2-formylthiazole via conversion to a organomagnesium intermediate. The stability of the tetrafluoroethoxy group in the above transformations was demonstrated.