Please use this identifier to cite or link to this item: http://hdl.handle.net/10995/27233
Title: Microwave-assisted palladium-catalyzed C-C coupling versus nucleophilic aromatic substitution of hydrogen (SN H) in 5-bromopyrimidine by action of bithiophene and its analogues
Authors: Verbitskiy, E. V.
Cheprakova, E. M.
Zhilina, E. F.
Kodess, M. I.
Ezhikova, M. A.
Pervova, M. G.
Slepukhin, P. A.
Subbotina, J. O.
Schepochkin, A. V.
Rusinov, G. L.
Chupakhin, O. N.
Charushin, V. N.
Issue Date: 2013
Citation: Microwave-assisted palladium-catalyzed C-C coupling versus nucleophilic aromatic substitution of hydrogen (SN H) in 5-bromopyrimidine by action of bithiophene and its analogues / E. V. Verbitskiy, E. M. Cheprakova, E. F. Zhilina [et al.] // Tetrahedron. — 2013. — Vol. 69. — № 25. — P. 5164-5172.
Abstract: 5-Bromopyrimidine reacts with 2,2′-bithiophene, [2,2′:5′, 2″]terthiophene and 2-phenylthiophene in the presence of a palladium catalyst to give 5-(het)aryl substituted pyrimidines due to the palladium-catalyzed aryl-aryl C-C coupling. However 5-bromo-4-(het)aryl- pyrimidines have been prepared from the same starting materials through the SN H-reaction catalyzed by a Lewis acid. Conditions for both types of reactions were optimized. All components of the reaction mixtures, including by-products, have been elucidated by gas-liquid chromatography/mass- spectrometry. Evidence for the structure of 4- and 5-bithiophenyl-substituted pyrimidines has first been obtained by means of X-ray crystallography analysis. Molecular orbital calculations (TDDFT), as well as the redox and optical measurements for all new compounds have also been performed. © 2013 Elsevier Ltd. All rights reserved.
Keywords: C-H BOND ACTIVATIONS
MICROWAVE-ASSISTED SYNTHESIS
NUCLEOPHILIC AROMATIC SUBSTITUTION OF HYDROGEN
PALLADIUM
PYRIMIDINES
2 PHENYLTHIOPHENE
2,2' DITHIOPHENE
5 BROMOPYRIMIDINE
[2,2':5',2'']TERTHIOPHENE
CHEMICAL COMPOUND
HYDROGEN
LEWIS ACID
PALLADIUM
PYRIMIDINE DERIVATIVE
UNCLASSIFIED DRUG
ARTICLE
ARYLATION
CALCULATION
CATALYST
CHEMICAL STRUCTURE
COVALENT BOND
LIQUID CHROMATOGRAPHY
MASS FRAGMENTOGRAPHY
MEASUREMENT
MICROWAVE RADIATION
NUCLEOPHILICITY
PRIORITY JOURNAL
REACTION OPTIMIZATION
SUBSTITUTION REACTION
X RAY CRYSTALLOGRAPHY
URI: http://hdl.handle.net/10995/27233
SCOPUS ID: 84877725521
WOS ID: WOS:000319647600015
PURE ID: 902269
ISSN: 0040-4020
DOI: 10.1016/j.tet.2013.04.062
Appears in Collections:Научные публикации, проиндексированные в SCOPUS и WoS CC

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