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

Mykhaylo V Vovk; Oleksandr M Pinchuk; Andrij O Tolmachov; Andrei A Gakh

doi:10.3390/molecules15020997

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

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

Authors

Mykhaylo V Vovk¹, Oleksandr M Pinchuk, Andrij O Tolmachov, Andrei A Gakh

Affiliation

¹ Institute of Organic Chemistry, NAS of Ukraine, Murmanska 5, 02094 Kyiv, Ukraine. mvovk@ioch.kiev.ua

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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Cyclization
Pyrroles / chemical synthesis*
Pyrroles / chemistry
Transition Temperature

Substances

Pyrroles