Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 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.

PubMed Disclaimer

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).
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

References

    1. Fürstner A. Chemistry and biology of roseophilin and the prodigiosin alkaloids: A survey of the last 2500 years. Angew. Chem. Int. Ed. 2003;42:3582–3603. doi: 10.1002/anie.200300582. - DOI - PubMed
    1. Tsukamoto S., Tane K., Ohta T., Matsunaga S., Fusetani N., van Soest R.W.M. Four new bioactive pyrrole-derived alkaloids from the marine sponge Axinella brevistyla. J. Nat. Prod. 2001;64:1576–1978. doi: 10.1021/np010280b. - DOI - PubMed
    1. Grube A., Köck M. Oxocyclostylidol, an intramolecular cyclized oroidin derivative from the marine sponge Stylissa caribica. J. Nat. Prod. 2006;69:1212–1214. doi: 10.1021/np050408f. - DOI - PubMed
    1. Bellina F., Rossi R. Synthesis and biological activity of pyrrole, pyrroline and pyrrolidine derivatives with two aryl group on adjacent positions. Tetrahedron. 2006;62:7213–7256. doi: 10.1016/j.tet.2006.05.024. - DOI
    1. La Regina G., Silvestri R., Artico M., Lavecchia A., Novellino E., Befani O., Turini P., Agostinelli E. New pyrrole inhibitors of monoamine oxidase: Synthesis, biological evaluation, and structural determinants of MAO-A and MAO-B selectivity. J. Med. Chem. 2007;50:922–931. doi: 10.1021/jm060882y. - DOI - PubMed

Publication types

LinkOut - more resources