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Molecules 2010, 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

1
Institute of Organic Chemistry, NAS of Ukraine, Murmanska 5, 02094 Kyiv, Ukraine
2
National Taras Shevchenko University, Volodymyrs`ka 62, 01033 Kyiv, Ukraine
3
Oak Ridge National Laboratory, Oak Ridge, TN 37831-6242, USA
*
Authors to whom correspondence should be addressed.
Received: 26 December 2009 / Revised: 22 February 2010 / Accepted: 22 February 2010 / Published: 23 February 2010
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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.
Keywords: pyrrole; fluorinated heterocycles; Paal-Knorr reaction; trifluoromethoxy group; chain heterocyclization pyrrole; fluorinated heterocycles; Paal-Knorr reaction; trifluoromethoxy group; chain heterocyclization
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Vovk, M.V.; Pinchuk, O.M.; Tolmachov, A.O.; Gakh, A.A. Synthesis of 1-(4-Trifluoromethoxyphenyl)-2,5-dimethyl-3-(2-R-thiazol-4-yl)-1H-pyrroles via Chain Heterocyclization. Molecules 2010, 15, 997-1006.

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