Please use this identifier to cite or link to this item: http://hdl.handle.net/10995/51070
Title: Combination of the Suzuki-Miyaura cross-coupling and nucleophilic aromatic substitution of hydrogen (S N H) reactions as a versatile route to pyrimidines bearing thiophene fragments
Authors: Verbitskiy, Egor V.
Cheprakova, Ekaterina M.
Slepukhin, Pavel A.
Kodess, Mikhail I.
Ezhikova, Marina A.
Pervova, Marina G.
Rusinov, Gennady L.
Chupakhin, Oleg N.
Charushin, Valery N.
Issue Date: 2012
Citation: Combination of the Suzuki-Miyaura cross-coupling and nucleophilic aromatic substitution of hydrogen (S N H) reactions as a versatile route to pyrimidines bearing thiophene fragments / Egor V. Verbitskiy, Ekaterina M. Cheprakova, Pavel A. Slepukhin, Mikhail I. Kodess, Marina A. Ezhikova, Marina G. Pervova, Gennady L. Rusinov, Oleg N. Chupakhin, Valery N. Charushin // Tetrahedron. — 2012. — Vol. 68. — № 27-28. — P. 5445-5452.
Abstract: It has been shown that combination of the Suzuki-Miyaura cross-coupling and nucleophilic aromatic substitution of hydrogen is a versatile method for the synthesis of 4-(thiophen-2-yl)-, 5-(thiophen-2-yl)-, and 4,5-di(thiophen-2-yl) substituted pyrimidines from the commercially available 5-bromopyrimidine. The S N H (AE)- and S N H (AO)-reactions of 5-bromopyrimidine with thiophene and 2-bromothiophene have been studied by gas-liquid chromatography/mass-spectrometry. The structures of intermediate σ H-adducts, as well as thiophene-(thiophenyl)pyrimidine and bithiophene-(thiophenyl)pyrimidine dyads have first been established by X-ray crystallography analysis. © 2012 Elsevier Ltd. All rights reserved.
Keywords: MICROWAVE-ASSISTED SYNTHESIS
NUCLEOPHILIC AROMATIC SUBSTITUTION OF HYDROGEN
PYRIMIDINES
SUZUKI-MIYAURA REACTION
THIOPHENES
URI: http://hdl.handle.net/10995/51070
metadata.dc.rights: info:eu-repo/semantics/restrictedAccess
SCOPUS ID: 84862001348
WOS ID: WOS:000306350800016
PURE ID: 1078857
ISSN: 0040-4020
DOI: 10.1016/j.tet.2012.04.095
Appears in Collections:Научные публикации, проиндексированные в SCOPUS и WoS CC

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