Please use this identifier to cite or link to this item: http://hdl.handle.net/10995/51273
Title: Consecutive S N H and Suzuki-Miyaura cross-coupling reactions-an efficient synthetic strategy to pyrimidines bearing pyrrole and indole fragments
Authors: Verbitskiy, Egor V.
Rusinov, Gennady L.
Charushin, Valery N.
Chupakhin, Oleg N.
Cheprakova, Ekaterina M.
Slepukhin, Pavel A.
Pervova, Marina G.
Ezhikova, Marina A.
Kodess, Mikhail I.
Issue Date: 2012
Citation: Consecutive S N H and Suzuki-Miyaura cross-coupling reactions-an efficient synthetic strategy to pyrimidines bearing pyrrole and indole fragments / Egor V. Verbitskiy, Gennady L. Rusinov, Valery N. Charushin, Oleg N. Chupakhin, Ekaterina M. Cheprakova, Pavel A. Slepukhin, Marina G. Pervova, Marina A. Ezhikova, Mikhail I. Kodess // European Journal of Organic Chemistry. — 2012. — № 33. — P. 6612-6621.
Abstract: The combination of the Suzuki-Miyaura cross-coupling and nucleophilic aromatic substitution of hydrogen reactions is a versatile tool for the syntheses of 4-(1R-pyrrol-2-yl)-and 4-(1R-indol-3-yl)-5-(hetero)aryl-substituted pyrimidines from commercially available 5-bromopyrimidine. The S N H [AE, (addition-elimination)] and S N H [AO, (addition-oxidation)] reactions of 5-bromopyrimidine with pyrroles and indoles were studied by gas chromatography-mass spectrometry. The structures of the intermediate σ H adducts as well as the pyrrole-(hetero)arylpyrimidine and indole-(hetero)arylpyrimidine dyads were established for the first time by X-ray crystal structure analysis. © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Keywords: CROSS-COUPLING
MICROWAVE CHEMISTRY
NITROGEN HETEROCYCLES
NUCLEOPHILIC SUBSTITUTION
SYNTHETIC METHODS
URI: http://hdl.handle.net/10995/51273
https://elar.urfu.ru/handle/10995/51273
SCOPUS ID: 84869062762
WOS ID: 000310981500016
PURE ID: 1072349
ISSN: 1434-193X
DOI: 10.1002/ejoc.201201035
Appears in Collections:Научные публикации, проиндексированные в SCOPUS и WoS CC

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