volume 2009 issue 13 pages 2249-2259

Synthetic Approach to Alkoxy-β-(trifluoromethyl)styrenesand Their Application in the Synthesis of New TrifluoromethylatedHeterocycles

Vasiliy Muzalevskiy
Aleksey Shastin
Gunter Haufe
Publication typeJournal Article
Publication date2009-05-12
scimago Q2
wos Q2
SJR0.559
CiteScore4.6
Impact factor2.3
ISSN00397881, 1437210X
Catalysis
Organic Chemistry
Abstract
A new convenient stereoselective pathway to alkoxy-β-(trifluoromethyl)styrenes is described. Reactions of β-chloro- and β-bromo-β-(trifluoromethyl)styrenes with sodium methoxide and potassium tert-butoxide led to methoxy- and tert-butoxy-β-(trifluoromethyl)styrenes in good to excellent yields. Bromination of tertbutoxy-β-(trifluoromethyl)styrenes proceeded with formation of aryl(bromo)methyl trifluoromethyl ketones. The latter compounds were found to be useful starting materials for the synthesis of different heterocyclic compounds bearing a trifluoromethyl group. In this way trifluoromethylated derivatives of imidazopyridine, imidazopyrimidine, imidazobenzimidazole, imidazothiazole, thiazole, and aminothiazole were obtained in moderate to high yield.
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GOST |
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GOST Copy
Muzalevskiy V. M. et al. Synthetic Approach to Alkoxy-β-(trifluoromethyl)styrenesand Their Application in the Synthesis of New TrifluoromethylatedHeterocycles // Synthesis. 2009. Vol. 2009. No. 13. pp. 2249-2259.
GOST all authors (up to 50) Copy
Muzalevskiy V. M., Nenajdenko V. G., Muzalevskiy V., Shastin A., Haufe G. Synthetic Approach to Alkoxy-β-(trifluoromethyl)styrenesand Their Application in the Synthesis of New TrifluoromethylatedHeterocycles // Synthesis. 2009. Vol. 2009. No. 13. pp. 2249-2259.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1055/s-0029-1216697
UR - https://doi.org/10.1055/s-0029-1216697
TI - Synthetic Approach to Alkoxy-β-(trifluoromethyl)styrenesand Their Application in the Synthesis of New TrifluoromethylatedHeterocycles
T2 - Synthesis
AU - Muzalevskiy, Vasily M.
AU - Nenajdenko, Valentine G.
AU - Muzalevskiy, Vasiliy
AU - Shastin, Aleksey
AU - Haufe, Gunter
PY - 2009
DA - 2009/05/12
PB - Georg Thieme Verlag KG
SP - 2249-2259
IS - 13
VL - 2009
SN - 0039-7881
SN - 1437-210X
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2009_Muzalevskiy,
author = {Vasily M. Muzalevskiy and Valentine G. Nenajdenko and Vasiliy Muzalevskiy and Aleksey Shastin and Gunter Haufe},
title = {Synthetic Approach to Alkoxy-β-(trifluoromethyl)styrenesand Their Application in the Synthesis of New TrifluoromethylatedHeterocycles},
journal = {Synthesis},
year = {2009},
volume = {2009},
publisher = {Georg Thieme Verlag KG},
month = {may},
url = {https://doi.org/10.1055/s-0029-1216697},
number = {13},
pages = {2249--2259},
doi = {10.1055/s-0029-1216697}
}
MLA
Cite this
MLA Copy
Muzalevskiy, Vasily M., et al. “Synthetic Approach to Alkoxy-β-(trifluoromethyl)styrenesand Their Application in the Synthesis of New TrifluoromethylatedHeterocycles.” Synthesis, vol. 2009, no. 13, May. 2009, pp. 2249-2259. https://doi.org/10.1055/s-0029-1216697.