Research output: Contribution to journal › Article › peer-review
An Azirine Strategy for the Synthesis of Alkyl 4-Amino-5-(trifluoromethyl)-1 H -pyrrole-2-carboxylates. / Funt, Liya D.; Tomashenko, Olesya A.; Novikov, Mikhail S.; Khlebnikov, Alexander F.
In: Synthesis, Vol. 50, No. 24, ss-2018-z0644-fa, 17.12.2018, p. 4809-4822.Research output: Contribution to journal › Article › peer-review
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TY - JOUR
T1 - An Azirine Strategy for the Synthesis of Alkyl 4-Amino-5-(trifluoromethyl)-1 H -pyrrole-2-carboxylates
AU - Funt, Liya D.
AU - Tomashenko, Olesya A.
AU - Novikov, Mikhail S.
AU - Khlebnikov, Alexander F.
PY - 2018/12/17
Y1 - 2018/12/17
N2 - 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 H-2/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.
AB - 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 H-2/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.
KW - trifluoromethylpyrrole
KW - aminopyrrole
KW - trifluoromethylated pyridinium ylide
KW - pyridine
KW - piperidine
KW - PHENYL-PYRIDINIUM CHLORIDE
KW - TRIFLUOROMETHYLATED PYRROLES
KW - 3+2 CYCLOADDITION
KW - 2H-AZIRINES
KW - ISOXAZOLES
KW - BETAINES
UR - http://www.scopus.com/inward/record.url?scp=85058012775&partnerID=8YFLogxK
UR - http://www.thieme-connect.de/DOI/DOI?10.1055/s-0037-1610840
UR - http://www.mendeley.com/research/azirine-strategy-synthesis-alkyl-4amino5trifluoromethyl1hpyrrole2carboxylates
U2 - 10.1055/s-0037-1610840
DO - 10.1055/s-0037-1610840
M3 - статья
VL - 50
SP - 4809
EP - 4822
JO - Synthesis
JF - Synthesis
SN - 0039-7881
IS - 24
M1 - ss-2018-z0644-fa
ER -
ID: 36831502