Please use this identifier to cite or link to this item: http://hdl.handle.net/10995/26840
Title: Synthesis and reactivity of 5-polyfluoroalkyl-5-deazaalloxazines
Authors: Dudkin, S.
Iaroshenko, V. O.
Sosnovskikh, V. Y.
Tolmachev, A. A.
Villinger, A.
Langer, P.
Issue Date: 2013
Citation: Synthesis and reactivity of 5-polyfluoroalkyl-5-deazaalloxazines / S. Dudkin, V. O. Iaroshenko, V. Y. Sosnovskikh [et al.] // Organic and Biomolecular Chemistry. — 2013. — Vol. 11. — № 32. — P. 5351-5361.
Abstract: Reaction of 6-arylamino-1,3-dialkyluracils with anhydrides of polyfluorocarboxylic acids in the presence of pyridine and subsequent cyclization with concentrated H2SO4 gave the corresponding 1,3-dialkyl-5-(polyfluoroalkyl)pyrimido[4,5-b]quinoline-2,4(1H,3H)-diones (5-polyfluoroalkyl-5-deazaalloxazines). The reactivity of these compounds towards nucleophilic reagents, such as sodium cyanoborohydride, acetophenone, nitromethane, potassium cyanide, indole and p-thiocresol, as well as Suzuki and Sonogashira couplings are described. The nucleophilic addition takes place at the 5-position of the 5-deazaalloxazine system and is in many cases irreversible to give 5,10-dihydropyrimido[4,5-b]quinoline-2,4(1H,3H)-dione derivatives in good to excellent yields.© 2013 The Royal Society of Chemistry.
Keywords: ACETOPHENONES
NITROMETHANE
NUCLEOPHILIC ADDITIONS
NUCLEOPHILIC REAGENT
POTASSIUM CYANIDES
SODIUM CYANOBOROHYDRIDE
SONOGASHIRA COUPLING
ADDITION REACTIONS
KETONES
SYNTHESIS (CHEMICAL)
CYCLIZATION
DRUG DERIVATIVE
HETEROCYCLIC COMPOUND
ISOALLOXAZINE
PYRIDINE
PYRIDINE DERIVATIVE
QUINOLINE DERIVATIVE
RIBOFLAVIN DERIVATIVE
URACIL
ALKYLATION
ARTICLE
CHEMISTRY
CYCLIZATION
HALOGENATION
SYNTHESIS
ALKYLATION
AZA COMPOUNDS
CYCLIZATION
FLAVINS
HALOGENATION
PYRIDINES
QUINOLINES
URACIL
URI: http://hdl.handle.net/10995/26840
SCOPUS ID: 84880861247
WOS ID: WOS:000322944900017
PURE ID: 878889
ISSN: 1477-0520
DOI: 10.1039/c3ob26837c
Appears in Collections:Научные публикации, проиндексированные в SCOPUS и WoS

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