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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://elar.urfu.ru/handle/10995/26840 |
SCOPUS ID: | 84880861247 |
WOS ID: | 000322944900017 |
PURE ID: | 878889 |
ISSN: | 1477-0520 |
DOI: | 10.1039/c3ob26837c |
Appears in Collections: | Научные публикации ученых УрФУ, проиндексированные в SCOPUS и WoS CC |
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