R 30 Reaction of 6-nitro-1.2.4-triazolo[1.5-a]pyrimidines with benzylamine - an unusual synthesis of 1-hydroxymidazoles [Electronic resource] / V. L. Rusinov, M. N. Kushnir, O. N. Chupakhin, G. G. Alexandrov // Mendeleev Communications. - 1993. - N 5. - P213-214 . - ISSN 0959-9436 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Heating of 5-methyl-6-nitro-7-p-N,N-dimethylaminophenyl)-1,2,4-triazolo[1,5-a]pyrimidines with benzylamine in ethanol or DMF leads to 1-hyroxy-2-phenyl-4-methyl-5-benylimino(p-N,N-dimethylaminophenyl)methylidinomidazole |
Щ 61 Щербаков, К. В. Реакции 5,6,7,8-тетрафтор-2(3)-этоксикарбонилхромонов с метиламином [] = Reactions of 5,6,7,8-tetrafluoro-4-hydroxycoumarin derivatives with benzylamine and aniline / К. В. Щербаков, Я. В. Бургарт, В. И. Салоутин // Изв. АН. Сер. Химическая. - 2005. - N 9. - 2093-2098: рис. - Библиогр. : с. 2098 (13 назв.) . - ISSN 0002-3353 Рубрики: Химические науки Аннотация: 5.6.7.8-Тетрафтор-2-этоксикарбонилхромон реагирует с метиламином неоднозначно в зависимости от использованного растворителя и количества амина: в ДМСО и MeCN - первоначальнопо положению С(7) с замещением атома фтора, и далее по центрам С(2) и/или С(9), а в этаноле - по центру С(2) с раскрытием пиронового цикла. 2-Метил-5,6,7,8-тетрафтор-3-этоксикарбонилхромон реагирует с метиламином независимо от растворителя с раскрытием хромонового цикла и промежуточным образованием этил-2-(1-метиламино)этилиден-3-(2-гидрокси-3,4,5,6-тетрафторфенил)-3-оксопропионата, из которого в результате внутримолекулярной циклизации получен 3-(1-метил-амино)этилиден-5,6,7,8-тетрафтор-3.4-дигидро-2H-бензопиран-2,4-дион |
S 53 Shcherbakov, K. V. Reactions of 5,6,7,8-tetrafluoro-4-hydroxycoumarin derivatives with benzylamine and aniline [Electronic resource] / K. V. Shcherbakov, Ya. V. Burgart, V. I. Saloutin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2006. - Vol. 55, № 7. - P1215-1219 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 5,6,7,8-Tetrafluoro-4-hydroxycoumarin reacted with benzylamine under mild conditions to give a stable salt, while its refluxing with aniline or benzylamine in xylene afforded 5,6,7,8-tetrafluoro-4-phenyl(benzyl)aminocoumarins. Reactions of 3-acetyl(acetimidoyl)-5,6,7,8-tetrafluoro-4-hydroxycoumarins with benzylamine followed different pathways, depending on the solvent. Condensation at the acyl substituent can be accompanied by replacement of the F atom in position 7. 3-Acetylcoumarin formed a salt, while 3-acetimidoylcoumarin yielded a 7-monosubstituted product. 3-Acetyl(acetimidoyl)-5,6,7,8-tetrafluoro-4-hydroxycoumarins reacted with aniline to give only 5,6,7,8-tetrafluoro-4-hydroxy-3-(N-phenylacetimidoyl)coumarin \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2006, 55 (7), 1215-1219.pdf |
S 53 Shcherbakov, K. V. Features of reactions of polyfluorinated ethyl 4-oxo-2-pnenyl-4H-chromene-3-carboxylates with N-nucleophiles [Electronic resource] / K. V. Shcherbakov, Ya. V. Burgart, V. I. Saloutin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2013. - Vol.49, №5. - С. 719-729. - Библиогр.: с. 729 (13 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): BENZYLAMINE -- CHROMONE-COUMARIN REARRANGEMENT -- TETRAFLUOROFLAVONES Аннотация: Ethyl 5,6,7,8-tetrafluoro-4-oxo-2-phenyl-4H-chromene-3-carboxylate in reactions with primary amines is characterized by a chromone-coumarin rearrangement affording 3-[amino(phenyl)methylene]-6,7,8-trifluoro-2H-chromene-2,4(3H)-diones, and ethyl 4-oxo-2-phenyl-5,6,7,8-tetrafluoro-4H-chromene-3-carboxylate characteristically adds the amine at the C2 site of the flavone furnishing 3-amino-3-phenyl-2-(2,3,4,5-tetrafluoro-6-hydroxybenzoyl)acrylates which depending on the substituent at the amino group are capable of intramolecular cyclization into 3-[(alkylamino)(phenyl)methylene]-5,6,7,8-tetrafluoro-2H-chromene-2,4(3H)-dione or in the case of benzylamine substituent, into ethyl 1-benzyl-5-hydroxy-4-oxo-2-phenyl-6,7,8-trifluoro-1,4-dihydroquinoline-3-carboxylate. The main process in the reaction of tri- and tetrafluoroflavones with secondary amine (1-methylpiperazine) is the nucleophilic substitution at the C7 of flavone. In the reaction with 1,2-phenylenediamine 3-[(2-aminophenyl)amino]-3-phenyl-2-(2,3,4,5-tetrafluoro-6-hydroxybenzoyl)acrylate was obtained from tetrafluoroflavone and 1H-benzimidazol-2-yl(3,4,5-trifluoro-2-hydroxyphenyl)methanone, from trifluoroflavone \\\\expert2\\NBO\\Russian Journal of Organic Chemistry\\2013, 49, (5), 719-729.pdf |