C 57 Chupakhin, O. N. Regioselectivity in the reactions of pyrroles with 3-aryl-1,2,4-triazin-5-ones [Electronic resource] / O. N. Chupakhin, G. V. Zyryanov, V. L. Rusinov // Mendeleev Communications. - 2001. - Vol. 11, № 2. - P77-78 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Depending on the nature of acylating agents, the reaction of 1-methylpyrrole with 3-aryl-1,2,4-triazin-5-ones leads to either ?- or ?-heteroarylpyrroles with a high degree of regioselectivity???? |
Z 99 Zyryanov, G. V. Easy formation of S-N(H) products in reactions of indoles and pyrroles with 3-aryl-1,2,4-triazin-5(2H)-ones in the presence of tosyl chloride [Electronic resource] / G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2002. - Vol. 51, № 6. - P1042-1044 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reactions of 3-aryl-1,2,4-triazin-5(2H)-ones with indoles and pyrroles in the presence of p-toluenesulfonyl chloride afforded 3-aryl-6-hetaryl-1,2,4-triazin-5(2H)-ones in high yields. The latter are products of the nucleophilic substitution of hydrogen \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2002, 51 (6), 1042-1044.pdf |
C 75 Consecutive S-N(H) and Suzuki–Miyaura Cross-Coupling Reactions – an Efficient Synthetic Strategy to Pyrimidines Bearing Pyrrole and Indole Fragments / E. V. Verbitskiy, G. L. Rusinov, V. N. Charushin, O. N. Chupakhin, E. M. Cheprakova, P. A. Slepukhin, M. G. Pervova, M. I. Kodess // European Journal of Organic Chemistry. - 2012. - Vol. 2012, №33. - С. 6612-6621 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SYNTHETIC METHODS -- CROSS-COUPLING -- NITROGEN HETEROCYCLES Аннотация: 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 SNH [AE, (addition–elimination)] and SNH [AO, (addition–oxidation)] reactions of 5-bromopyrimidine with pyrroles and indoles were studied by gas chromatography–mass spectrometry. The structures of the intermediate σH 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 \\\\Expert2\\nbo\\European Journal of Organic Chemistry\\2012, p.6612.pdf |
S 78 Spiroheterocyclization of methyl 1-Aryl-3-cinnamoyl-4,5-dioxo-4,5-dihydro- 1H-pyrrole-2-carboxylates by the action of 3-(Arylamino)-1H-inden-1-ones [Электронный ресурс] / P. S. Silaichev, V. O. Filimonov, P. A. Slepukhin, A. N. Maslivets // Molecules. - 2012. - Vol.17, №12. - P13787-13794 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ENAMINES -- PYRROLE-2,3-DIONES -- SPIRO[INDENO[1,2-b]PYRROLE-3,2'-PYRROLES] Аннотация: Methyl 1-Aryl-3-cinnamoyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates interact with 3-(arylamino)-1H-inden-1-ones to give the corresponding 1,1'-diaryl-3'- cinnamoyl-4'-hydroxy-1H-spiro[indeno[1,2-b]pyrrole-3,2'-pyrrole] -2,4,5'(1'H)-triones in good yields. |
A 23 Aerobic oxidative C-H/C-H coupling of azaaromatics with indoles and pyrroles in the presence of TiO2 as a photocatalyst [Electronic resource] / I. A. Utepova, M. A. Trestsova, O. N. Chupakhin, V. N. Charushin, A. A. Rempel // Green Chemistry. - 2015. - Vol. 17, № 8. - С. 4401-4410. - Bibliogr. : p. 4409-4410 (30 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): BOND ACTIVATION -- INHIBITORS -- HYDROGEN Аннотация: In this paper we wish to report a highly selective and benign method for the double C-H/C-H coupling of azaaromatics with indoles or pyrrole in the presence of air oxygen/TiO2, as an effective photocatalytic oxidative system. It has been shown that this versatile approach can be applied for direct C-H functionalisation of a variety of azaaromatic systems, such as mono-, di- and triazines, substituted and unsubstituted azines and their benzo-annelated analogues. \\\\expert2\\nbo\\Green Chemistry\\2015, v.17, N 8, p.4401-4410.pdf |
A 10 A facile, metal-free, oxidative coupling of new 6-(hetero)aryl-[1,2,5]oxadiazolo[3,4-b]pyrazines with pyrroles, indoles and carbazoles. / Yu. A. Kvashnin, N. A. Kazin, E. V. Verbitskiy, T. S. Svalova, A. V. Ivanova, A. Kozitsina, P. A. Slepukhin, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // ARKIVOC. - 2016. - Vol. V. - С. 279-300. - Bibliogr. : p. 297-300 (45 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRAZINES -- PYRROLES -- INDOLES \\\\expert2\\NBO\\ARKIVOC\\2016, p.279-300.pdf |
S 98 Synthesis of a new class of carbinol linked bis-heterocycles via the reaction of 2-(trifluoroacetyl)chromones with indoles and pyrroles / A. V. Safrygin, R. A. Irgashev, M. A. Barabanov, V. Ya. Sosnovskikh // Tetrahedron. - 2016. - Vol. 72. - С. 227-233. - Bibliogr. : p. 233 (25 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SYNTHESIS -- CARBINOL LINKED BIS-HETEROCYCLES -- INDOLES \\\\expert2\\nbo\\Tetrahedron\\2016, v. 72 , p. 227-233.pdf |
Iron(III)-catalyzed multicomponent synthesis of highly substituted pyrroles under ball-milling conditions / A. Mukherjee, S. Al-Ghezi Basim, G. V. Zyryanov, O. N. Chupakhin // Современные синтетические методологии для создания лекарственных препаратов и функциональных материалов" (MOSM 2021): V международная конференция: сборник тезисов. - Екатеринбург, 2021. - C. PR-186 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Nowadays, green chemistry plays an important role for environment. In this context, development of solvent-free ball milling or a grinding approach has attracted considerable interest in organic synthesis.1 Hence, carrying out a reaction under solvent-free conditions and at room temperature is an effective approach to eliminate the use of volatile organic compounds and to obtain the greenness in the process. On the other hands, pyrroles are the small aromatic, nitrogen-containing heterocyclic compounds present in many natural products.2 Pyrrole molecules show important biological relevance such as porphyrins, bile pigments, and coenzymes and are known to exhibit various applications as organic materials.3 In this work, we have presented a highly robust one-pot, four-component cascade cyclization reaction of α-keto aldehydes, anilines, activated alkynes, and aromatic nucleophiles to synthesize a diverse range of pharmaceutically important penta-substituted pyrroles. The reaction proceeded smoothly under ball-milling conditions in presence of iron catalyst. |
Direct C−H functionalization of calix[N](het)arenes (N=4,6): a brief update / A. Mukherjee, D. S. Kopchuk, I. S. Kovalev [et al.] // ChemistrySelect. - 2022. - Vol. 7, № 12. - Pe202103017 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Calix[n]arenes, their hetero derivatives, are the most popular hosts for the supramolecular and materials chemistry as they can form stable inclusion complexes with charged or neutral molecules, including gases. This short review highlights the most prospective synthetic approaches for direct modification of calix[4]arene core with various functional moieties as well as selected patterns of direct C−H-modification of calix[6]arenes and calix[4]pyrroles. |