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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Correspondence to Yurii L. Yagupolskii.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(1), 80–87

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Davydova, Y.А., Sokolenko, T.M., Vlasenko, Y.G. et al. Chemical properties of 5-(1,1,2,2-tetrafluoroethoxy)-4-phenylthiazole derivatives. Chem Heterocycl Comp 51, 80–87 (2015). https://doi.org/10.1007/s10593-015-1663-z

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  • DOI: https://doi.org/10.1007/s10593-015-1663-z

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