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. 2010 Feb 23;15(2):997-1006.
doi: 10.3390/molecules15020997.

Synthesis of 1-(4-trifluoromethoxyphenyl)-2,5-dimethyl-3-(2-R-thiazol-4-yl)-1H-pyrroles via chain heterocyclization

Mykhaylo V Vovk  1 , Oleksandr M Pinchuk, Andrij O Tolmachov, Andrei A Gakh
Affiliations

Synthesis of 1-(4-trifluoromethoxyphenyl)-2,5-dimethyl-3-(2-R-thiazol-4-yl)-1H-pyrroles via chain heterocyclization

Mykhaylo V Vovk et al. Molecules. .

Abstract

The title compounds, (4-trifluoromethoxyphenyl)-2,5-dimethyl-3-(2-R-thiazol-4-yl)-1H-pyrroles, were prepared in four steps starting from commercially available 4-trifluoromethoxyaniline. The pyrrole (second ring) was added in one step using the Paal-Knorr method. The thiazole (third ring) was added in three steps using chloroacylation with chloroacetonitrile followed by heterocyclization with thioamides/thioureas.

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Figures

Scheme 1
Scheme 1
Synthesis of 3-chloroacetylpyrrole (5).
Scheme 2
Scheme 2
Synthesis of 4-trifluoromethoxyphenyl substituted pyrroles 6-9 (R1-R5: see Table 1).
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