Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
Transformation of fluorinated 2-alkynylanilines by various catalytic systems. / Politanskaya, Larisa; Petyuk, Maxim; Tretyakov, Evgeny.
в: Journal of Fluorine Chemistry, Том 228, 109394, 01.12.2019.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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TY - JOUR
T1 - Transformation of fluorinated 2-alkynylanilines by various catalytic systems
AU - Politanskaya, Larisa
AU - Petyuk, Maxim
AU - Tretyakov, Evgeny
N1 - The authors thank the Russian Foundation for Basic Research (grant No 19-53-53003) for financial support and the Chemical Service Center SB RAS for spectral and analytical measurements.
PY - 2019/12/1
Y1 - 2019/12/1
N2 - Simple and efficient approaches to the synthesis of fluorinated benzoazaheterocycles with good yields are reported. Firstly a series of polyfluorinated 2-alkynylanilines – the versatile building blocks – was synthesized by the Sonogashira reaction of o-iodoaniline with terminal alkynes. Then the transformations of the obtained 2,3,4-trifluo-6-alkynilanilines in the presence of KOH or PdCl2 in MeCN, and in the presence of monohydrate of p-toluenesulfonic acid (p-TSA•H2O) in MeOH, EtOH or benzene were investigated. It was found that Ph- and n-Bu-containing alkynylanilines by action of PdCl2 in MeCN underwent an intramolecular cyclization reaction to produce the corresponding indoles in high yields. The reaction of KOH with alkynes containing the tertiary alcohol function at the triple bond produced the unsubstituted on the pyrrole ring indole. It was found that fluorinated 2-alkynilanilines can be transformated into indoles, 2-arylketones and 2,3-dihydroquinolines by action of p-TSA•H2O in boiling alcohols, depending on the substituent at the triple bond. The use of benzene as a solvent in the reaction of p-TSA•H2O with polyfluorinated alkynes, bearing an alcohol group resulted in representative series of 2,3-dihydroquinolinones containing a substituents R1 and R2 in the 2nd position of their structure (R = H, H; Me, Me; H, i-Pr; H, Ph).
AB - Simple and efficient approaches to the synthesis of fluorinated benzoazaheterocycles with good yields are reported. Firstly a series of polyfluorinated 2-alkynylanilines – the versatile building blocks – was synthesized by the Sonogashira reaction of o-iodoaniline with terminal alkynes. Then the transformations of the obtained 2,3,4-trifluo-6-alkynilanilines in the presence of KOH or PdCl2 in MeCN, and in the presence of monohydrate of p-toluenesulfonic acid (p-TSA•H2O) in MeOH, EtOH or benzene were investigated. It was found that Ph- and n-Bu-containing alkynylanilines by action of PdCl2 in MeCN underwent an intramolecular cyclization reaction to produce the corresponding indoles in high yields. The reaction of KOH with alkynes containing the tertiary alcohol function at the triple bond produced the unsubstituted on the pyrrole ring indole. It was found that fluorinated 2-alkynilanilines can be transformated into indoles, 2-arylketones and 2,3-dihydroquinolines by action of p-TSA•H2O in boiling alcohols, depending on the substituent at the triple bond. The use of benzene as a solvent in the reaction of p-TSA•H2O with polyfluorinated alkynes, bearing an alcohol group resulted in representative series of 2,3-dihydroquinolinones containing a substituents R1 and R2 in the 2nd position of their structure (R = H, H; Me, Me; H, i-Pr; H, Ph).
KW - 2,3-Dihydroquinolinones
KW - Cross-coupling
KW - Fluorinated alkynes
KW - Fluorinated heterocycles
KW - Triple bond hydration
KW - ALCOHOLS
KW - CYTOTOXICITY EVALUATION
KW - EFFICIENT SYNTHESIS
KW - REGIOSELECTIVE TRANSFORMATION
KW - ALKYNES
KW - CLEAVAGE
KW - HYDRATION
UR - http://www.scopus.com/inward/record.url?scp=85074458188&partnerID=8YFLogxK
U2 - 10.1016/j.jfluchem.2019.109394
DO - 10.1016/j.jfluchem.2019.109394
M3 - Article
AN - SCOPUS:85074458188
VL - 228
JO - Journal of Fluorine Chemistry
JF - Journal of Fluorine Chemistry
SN - 0022-1139
M1 - 109394
ER -
ID: 22344632