volume 50 issue 24 pages 4809-4822

An Azirine Strategy for the Synthesis of Alkyl 4-Amino-5-(trifluoromethyl)-1 H -pyrrole-2-carboxylates

Liya Funt
Olesya Tomashenko
Publication typeJournal Article
Publication date2018-11-15
scimago Q2
wos Q2
SJR0.559
CiteScore4.6
Impact factor2.3
ISSN00397881, 1437210X
Catalysis
Organic Chemistry
Abstract

1-(3,3,3-Trifluoro-2,2-dihydroxypropyl)pyridin-1-ium bromide serves as a trifluoromethyl-containing building block for the preparation of trifluoromethyl-substituted aminopyrroles based on the 2H-azirine ring expansion strategy. The primary products, 3-aryl-2-(methoxycarbonyl)-4-(pyridin-1-ium-1-yl)-5-(trifluoromethyl)pyrrol-1-ides, can be hydrogenated by H2/PtO2 to form alkyl 3-aryl-4-(piperidin-1-yl)-5-(trifluoromethyl)-1H-pyrrole-2-carboxylates and transformed into alkyl 4-amino-3-aryl-1-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylates via methylation/hydrazinolysis.

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GOST Copy
Khlebnikov A. F. et al. An Azirine Strategy for the Synthesis of Alkyl 4-Amino-5-(trifluoromethyl)-1 H -pyrrole-2-carboxylates // Synthesis. 2018. Vol. 50. No. 24. pp. 4809-4822.
GOST all authors (up to 50) Copy
Khlebnikov A. F., Funt L., Tomashenko O., Novikov M., Tomashenko O. A. An Azirine Strategy for the Synthesis of Alkyl 4-Amino-5-(trifluoromethyl)-1 H -pyrrole-2-carboxylates // Synthesis. 2018. Vol. 50. No. 24. pp. 4809-4822.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1055/s-0037-1610840
UR - https://doi.org/10.1055/s-0037-1610840
TI - An Azirine Strategy for the Synthesis of Alkyl 4-Amino-5-(trifluoromethyl)-1 H -pyrrole-2-carboxylates
T2 - Synthesis
AU - Khlebnikov, Alexander F
AU - Funt, Liya
AU - Tomashenko, Olesya
AU - Novikov, Mikhail
AU - Tomashenko, Olesya A
PY - 2018
DA - 2018/11/15
PB - Georg Thieme Verlag KG
SP - 4809-4822
IS - 24
VL - 50
SN - 0039-7881
SN - 1437-210X
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2018_Khlebnikov,
author = {Alexander F Khlebnikov and Liya Funt and Olesya Tomashenko and Mikhail Novikov and Olesya A Tomashenko},
title = {An Azirine Strategy for the Synthesis of Alkyl 4-Amino-5-(trifluoromethyl)-1 H -pyrrole-2-carboxylates},
journal = {Synthesis},
year = {2018},
volume = {50},
publisher = {Georg Thieme Verlag KG},
month = {nov},
url = {https://doi.org/10.1055/s-0037-1610840},
number = {24},
pages = {4809--4822},
doi = {10.1055/s-0037-1610840}
}
MLA
Cite this
MLA Copy
Khlebnikov, Alexander F., et al. “An Azirine Strategy for the Synthesis of Alkyl 4-Amino-5-(trifluoromethyl)-1 H -pyrrole-2-carboxylates.” Synthesis, vol. 50, no. 24, Nov. 2018, pp. 4809-4822. https://doi.org/10.1055/s-0037-1610840.