Synthesis and reactivity of 5-polyfluoroalkyl-5-deazaalloxazines / Dudkin Sergii,Iaroshenko Viktor O.,Sosnovskikh Vyacheslav Ya,Tolmachev Andrey A.,Villinger Alexander,Langer Peter // ORGANIC \& BIOMOLECULAR CHEMISTRY. - 2013. - V. 11, l. 32. - P. 5351-5361.

ISSN/EISSN:

1477-0520 / 1477-0539

Type:

Article

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-(polyfluoroakyl)pyrimido{[}4,5-b]quinoline-2,4(1H,3H)-dion es (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.

Author keywords:

ADENOSINE-DEAMINASE; 8-SUBSTITUTED 5-DEAZAFLAVINS; OXIDATIVE CYCLIZATION; CONVENIENT SYNTHESIS; INHIBITORS; ANALOGS; 5-DEAZAALLOXAZINES; NUCLEOPHILES; NUCLEOSIDES; PALLADIUM

DOI:

10.1039/c3ob26837c

Web of Science ID:

ISI:000322944900017

Соавторы в МНС:

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Другие поля

Поле	Значение
Month	AUG 28
Publisher	ROYAL SOC CHEMISTRY
Address	THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND
Language	English
EISSN	1477-0539
Keywords-Plus	ADENOSINE-DEAMINASE; 8-SUBSTITUTED 5-DEAZAFLAVINS; OXIDATIVE CYCLIZATION; CONVENIENT SYNTHESIS; INHIBITORS; ANALOGS; 5-DEAZAALLOXAZINES; NUCLEOPHILES; NUCLEOSIDES; PALLADIUM
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	peter.langer@uni-rostock.de
ResearcherID-Numbers	Iaroshenko, Viktor/I-6150-2015
Number-of-Cited-References	56
Usage-Count-Since-2013	11
Journal-ISO	Org. Biomol. Chem.
Doc-Delivery-Number	198TJ