T 82 Transformations of 5-diazo derivatives of 1,3-dimethyl-6-hydrazinouracil - new synthetic approaches to novel pyrimidine-derivatives [Electronic resource] / Y. A. Azev, O. L. Guselnikova, O. N. Chupakhin // Mendeleev Communications. - 1994. - N 6. - P208-209 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 1,3-Dimethyl-6-hydrazinouracil 1 gives hydrazones 2 with the corresponding aldehydes. Heating of 6-hydrazinouracil 1 in ethanol in the presence of hyrochloric acid results in the formation of N1, N2-bis(1,3-dimethyl-2,6-dioxopyrimid-4-yl)hydrazine 3, which gives the diazo derivative 4 on treatment with 2,4-diazido-6-cyanomethoxy-s-triazine in DMSO in the presence of triethylamine et room temperature |
U 62 Unusual dimerization of 1-ethyl-1,2,4-triazinium salts into 4a,4b,9,10-tetrahydro-1,3,6,8,8a,10a-hexaazaphenanthrenes [Text] / O. N. Chupakhin, B. V. Rudakov, S. G. Alexeev, V. N. Charushin, V. A. Chertkov // Tetrahedron Letters. - 1990. - Vol. 31, N 52. - P7665-7668 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 1-Ethyl-3-alkylthio-5-phenyl-1,2,4-triazinium tetrafluoroborates were found to undergo an unusual dimerization on treatment with triethylamine in methanol or ethanol solution. A mechanism for the formation of 4a,4b,9,10-tetrahydro-1,3,5,8,8a,10a-hexaaza-phenanthrenes is proposed |
C 51 Chemistry of O- and C-adducts derived from 1,4-diazinium salts: the use of tetrahydropyrazines in the synthesis of condensed systems [Electronic resource] / G. L. Rusinov, P. A. Slepukhin, V. N. Charushin, O. A. Dyachenko, O. N. Kazheva, A. N. Chekhlov, E. V. Verbitskiy, M. I. Kodess, O. N. Chupakhin // Mendeleev Communications. - 2006. - Vol. 16, № 1. - P26-29 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 1-Ethyl-2,3-dicyano-5-nitromethyl-6-methoxy-1,4,5,6-tetrahydropyrazine reacts with N-methylquinoxalinium iodide in the presence of triethylamine to form octahydro-2,4a,5,10-tetraazabenzo[b]fluorene-3,4-dicarbonitrile, while our attempts to obtain similar polycyclic products from stereoisomeric 5-(S)- and 5-(R)-(1`-nitroprop-1`-yl)-6-methoxy-1,4,5,6-tetrahydropyrazines derived from the reaction of 1-nitropropane with 2,3-dicyano-5,6-dimethoxy-1-ethyl-1,4,5,6-tetrahydropyrazine. \\\\Expert2\\nbo\\Mendeleev Communications\\2006, v.1, p.26.pdf |
A 53 An Unusually easy oxidative dequaternization of N-alkyl-1,2,4-triazinium salts [Electronic resource] / O. N. Chupakhin, B. V. Rudakov, P. McDermott, S. G. Alexeev, V. N. Charushin, F. Hegarty // Mendeleev Communications. - 1995. - Vol. 5, № 3. - P104-105 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Unusually easy dequaternization has been found to occur on treatment of 1-alkyl-3-morpholino-5-phenyl-1,2,4-triazinium iodides with triethylamine in alcohol or acetone solutions at room temperature; a plausible reaction mechanism has been advanced on the basis of NMR and kinetic studies \\\\expert2\\nbo\\Mendeleev Communications\\1995, v.5, N 3. p.104.pdf |
I-69 Intermolecular and intramolecular cycloaddition reactions of 1-ethyl-1,2,4-triazinium salts with alkynes [Electronic resource] / N. N. Mochul`skaya, A. A. Andreiko, V. N. Charushin, V. I. Solomonov // Mendeleev Communications. - 2001. - Vol. 11, № 1. - P19-20 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Azomethyne ylides generated from 3-alkylthio substituted 1-alkyl-5-aryl-1,2,4-triazinium salts 4a–c on treatment with triethylamine undergo 1,3-dipolar cycloaddition with dimethyl acetylenedicarboxylate to give pyrrolo[2,1-f] [1,2,4]triazines, while 1-ethyl-5- phenyl-1,2,4-triazinium salts 1a,b bearing the CC bond in the side-chain 3-alkynylthio substituent react with acetylenes to undergo either intermolecular 1,3-dipolar cycloaddition or intramolecular inverse electron demand Diels–Alder reactions???? \\\\expert2\\nbo\\Mendeleev Communications\\2001, v.11, N 1. p.19.pdf |
R 30 Reaction of fluoroalkyl-containing 1,3-dicarbonyl compounds with benzylideneacetone [Electronic resource] / Ya. V. Burgart, A. S. Fokin, I. T. Bazyl, V. I. Saloutin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1997. - Vol. 46, № 5. - P952-954 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reaction of fluoroalkyl-containing 1,3-dicarbonyl compounds with benzylideneacetone with the use of pyridine or triethylamine as a catalyst gave new 3-fluoroalkyl-4-ethoxycarbonyl(acyl)-5-phenylcyclohexan-3-ol-I-ones in yields of 16–33% \\\\Expert2\\nbo\\Russian Chemical Bulletin\\1997, 46 (5), 952.pdf |
F 70 Fluorine-containing Heterocycles. X. Acetoacetamides in the Synthesis of Fluorine-containing Chromone [Electronic resource] / G. N. Lipunova, E. V. Nosova, M. I. Kodess, V. N. Charushin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2004. - Vol. 40, № 8. - P1162-1166 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Fluorine-containing chromone-3-carboxamides were synthesized by reaction of tetra(penta)fluoro-benzoyl chlorides with acetoacetamides in dichloromethane in the presence of triethylamine. Nucleophilic substitution of fluorine atoms by amine rests in compounds synthesized was investigated \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2004, 40 (8), 1162.pdf |
F 70 Fluorine-containing pyrido[1,2-a]quinazolin-6-ones [Electronic resource] / E. V. Nosova, G. N. Lipunova, M. I. Kodess, E. B. Vasil'eva, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 10. - P2314-2318 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Reactions of 2-aminopyridine and 2-amino-5-methylpyridine with 2,3,4,5-tetrafluorobenzoyl chloride afforded N,N’-diaroylpyridinium salts, which were converted into 6H-pyrido[1,2-a]quinazolin-6-ones by refluxing in toluene in the presence of triethylamine. The angular structure of the tricyclic derivatives obtained was confirmed by 19F and 13C NMR spectroscopy and 2D heteronuclear HetCOR and HMBC experiments \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (10), 2314.pdf |
F 76 Formation of polynuclear palladium complexes with the benzimidazole-2-thiolate anion [Electronic resource] / M. O. Talismanova, A. A. Sidorov, G. G. Aleksandrov, V. N. Charushin, S. K. Kotovskaya, I. L. Eremenko, I. I. Moiseeva // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2008. - Vol. 57, № 1. - P47-55 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reactions of palladium(II) salts with 2-mercaptobenzimidazole (HL) and its 5,6-difluorinated derivative (HLF) were investigated. In the presence of hydrochloric acid, PdCl2 and K2PdCl4 react with HL and HLF in the ethanol—water and acetonitrile—water systems to form the mono-nuclear dicationic complexes [Pd(HL)4]Cl2 (1) and [Pd(LF)4]Cl2 (2). In the absence of HCl, the reactions afford the tetranuclear complex Pd4[(L)2(3-S,N-(L))2(S,N-(L))4] (3). The reaction of triethylamine with an ethanolic solution of 3 leads to degradation of 3 and the formation of the lantern-type dinuclear complex Pd2[2-(L)4] (4), in which the palladium atoms are in the nonequivalent coordination environment, PdN4 and PdS4. The reaction of K2PdCl4 with HL or HLF in the THF—water or acetonitrile—water systems (for the reaction with HLF) in the presence of Et3N produces the lantern-type dinuclear complexes Pd2[(?S,N-(L3))4] and Pd2[(S,N)(LF))4] (5), in which the metal atoms are in the equivalent coordination environment (cis-PdN2S2) \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2008, 57 (1), 47.pdf |
R 30 Reaction of pentafluorobenzoylpyruvic acid with amines [Electronic resource] / V. I. Saloutin, I. T. Bazyl, Z. E. Skryabina, P. N. Kondrat'ev, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1994. - Vol. 43, № 2. - P279-282 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CYCLIZATION -- INTRAMOLECULAR CYCLIZATION -- PRIMARY AMINES -- PENTAFLUOROBENZOYLPYRUVIC ACID Аннотация: Reactions of pentafluorobenzoylpyruvic acid with amines afford the respective enamines. The intramolecular cyclization of the latter results in N-substituted 4-quinolone-2-carboxylic acids. Ammonia and triethylamine favor the cyclization of pentafluorobenzoylpyruvic acid to 2-carboxychromone. \\\\Expert2\\nbo\\Russian Chemical Bulletin\\1994, 43 (2), 279.pdf |
S 17 Saloutina, L. V. Reactions of 2,3-epoxypolyfluoroalkanes with triethylamine [Electronic resource] / L. V. Saloutina, M. I. Kodess, A. Ya. Zapevalov // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1994. - Vol. 43, № 12. - P2057-2061 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reactions of 2,3-epoxyperfluoro- and 2,3-epoxy--hydropolyfluoroalkanes with excess triethylamine at elevated temperatures yield secondary alcohols, which are the reduction products of intermediate isomeric ketones. Ring-opening occurs preferentially from the side of the less bulky trifluoromethyl group in all compounds except 2,3-epoxy-6-hydroundecafluorohexane \\\\Expert2\\nbo\\Russian Chemical Bulletin\\1994, 43 (13), 2057-2061.pdf |
T 82 Transformations of 1,2,4-Triazines in Reactions with Nucleophiles: V. SNH and ipso-Substitution in the Synthesis and Transformations of 5-Cyano-1,2,4-triazines [Electronic resource] / D. N. Kozhevnikov, V. N. Kozhevnikov, I. S. Kovalev, V. L. Rusinov, O. N. Chupakhin, G. G. Aleksandrov // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2002. - Vol. 38, № 5. - P744-750 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The scope of functionalization of 1,2,4-triazines can be considerably extended via successive nucleophilic substitution of hydrogen (SN H) and ipso-substitution. A convenient procedure has been developed for direct cyanation of 1,2,4-triazine 4-oxides with acetone cyanohydrin in the presence of triethylamine. The cyano group in the resulting 5-cyano-1,2,4-triazines is readily replaced by reactions with various aliphatic alcohols and amines \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2002, 38 (5), 744.pdf |
S 73 Sosnovskikh, V. Ya. Reactions of 3-cyanochromones with primary amines: structures of the products [Electronic resource] / V. Ya. Sosnovskikh, V. S. Moshkin, M. I. Kodess // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2010. - Vol. 59, № 3. - P615-625 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 3-CYANOCHROMONES -- PRIMARY AMINES -- RECYCLIZATION Аннотация: Reactions of 3-cyanochromones with primary aromatic amines in boiling benzene gave mixtures of Z- and E-3-arylamino-2-(2-hydroxyaroyl)acrylonitriles and 2-amino-3-(aryl-iminomethyl)chromones. The latter can easily be obtained in the individual state when the reaction is carried out in the presence of triethylamine. In the case of primary aliphatic amines, the open-chain reaction product immediately undergoes cyclization into 3-alkyliminomethyl-2-aminochromones. The structures of the products were examined by 1D and 2D 1H, 13C, and 15N NMR spectroscopy in DMSO-d6 and CDCl3 \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2009, 59 (3), 615-625.pdf |
U 62 Unusual Expansion of the 1,2,4,5-Tetrazine Ring in [1,2,4]Triazolo[4,3-b]-[1,2,4,5]tetrazines Leading to [1,2,4,6]Tetrazepine Systems [Text] / I. N. Ganebnuikh, S. G. Tolshchina, R. I. Ishmetova, N. K. Ignatenko, P. A. Slepukhin, G. L. Rusinov, V. N. Charushin // European Journal of Organic Chemistry. - 2011. - № 12. - P2309-2318. - Bibliogr. : p. 2318 (22 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Expansion of the tetrazine ring has first been found to occur when [1,2,4]triazolo[4,3-b][1,2,4,5]tetrazines were allowed to react with CH-active compounds in acetonitrile in the presence of triethylamine to give the unexpected series of 8,9-dihydro-7H-[1,2,4]-triazolo[4,3-b][1,2,4,6] tetrazepine derivatives \\\\Expert2\\nbo\\European Journal of Organic Chemistry\\2011, p.2309.pdf |
D 44 Deprotonation of pyrazole and its analogs by aqueous copper acetate in the presence of triethylamine / M. A. Yakovleva , E. V. Kushan, N. S. Boltacheva, V. I. Filyakova, S. E. Nefedov // Russian Journal of Inorganic Chemistry (Zhurnal Neorganicheskoi Khimii). - 2012. - Vol. 57, № 2. - С. 181-192 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SECONDARY BUILDING UNITS -- MAGNETIC-PROPERTIES -- COORDINATION POLYMERS Аннотация: Deprotonation reactions of pyrazole and its analogs by aqueous copper acetate in benzene at room temperature in the presence of triethylamine were studied. Unlike 3,5-dimethylpyrazole, more acidic pyrazole, 5-methyl-3-trifluoromethylpyrazole, and 3,5-bis(trifluoromethyl)pyrazoles are deprotonated to give pyrazolate bridges. The structural features of the obtained compounds are discussed based on X-ray diffraction data \\\\Expert2\\nbo\\Russian Journal of Inorganic Chemistry\\2012, v. 57, N. 2, p.181-192.pdf |
R 30 Reactions of quinoxaline with 3-methyl-1-phenylpyrazol-5-one / Y. A. Azev, E. D. Oparinaa, I. S. Kovalev, P. A. Slepukhin, R. K. Novikova // Mendeleev Communications. - 2012. - Vol.22, №1. - С. 37-38 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): QUINOXALINES -- PHENYLPYRAZOL -- TRIETHYLAMINE Аннотация: Quinoxaline during the reaction with 3-methyl-1-phenylpyrazol-5-one in the presence of triethylamine at room temperature in dimethylsulfoxide eliminates o-phenylenediamine and gives 4,4’-methylene-bis(3-methyl-1-phenylpyrazol-5-one) and 1,1,2,2-tetrakis(5-methyl-2-oxo-2-phenyl-1,2-dihydro-3H-pyrazol-4-yl)ethane. The latter was proved to be the intermediate to form the above dipyrazolylmethane derivative \\\\Expert2\\nbo\\Mendeleev Communications\\2012, v.22, p. 37.pdf |
A 10 A convenient synthesis of new 5,11-dihydroindolo[3,2-b]carbazoles bearing thiophene, 2,2′-bithiophene or 2,2′:5′,2″-terthiophene units at C-2 and C-8 positions / R. A. Irgashev, N. A. Kazin, G. L. Rusinov, V. N. Charushin // Tetrahedron Letters. - 2017. - Vol. 58, № 32. - P3139-3142 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 5,11-DIHYDROINDOLO[3,2-B]CARBAZOLE -- THIOPHENE -- 3-CHLOROACRYLALDEHYDE -- THE VILSMEIER–HAACK FORMYLATION -- THE FIESSELMANN REACTION Аннотация: A series of new 5,11-dihydroindolo[3,2-b]carbazole derivatives, containing functional thiophene, 2,2′-bithiophene or 2,2′:5′,2″-terthiophene moieties at both C-2 and C-8 positions of their fused scaffolds, have been obtained from 2,8-diacetyl-substituted 5,11-dihydroindolo[3,2-b]carbazole compounds through the effective strategy, which is based on the sequence of two reactions, namely the Vilsmeier–Haack formylation and the Fiesselmann thiophene synthesis. The starting acetyl substituted materials have been transformed into the corresponding 3-chlorocrylaldehyde-containing compounds by treatment with POCl3-DMF complex, followed by the reaction with alkyl thioglycolates or α-mercaptoacetone in the presence of triethylamine to afford 2-carboalkoxythiophene- or 2-acetylthiophene-linked derivatives. 2-Acetylthiophene derivatives have further been involved into the same sequence of reactions to obtain 2,2′-bithiophene-, and 2,2′:5′,2″-terthiophene-linked 5,11-dihydroindolo[3,2-b]carbazole compounds. \\\\Expert2\\NBO\\Tetrahedron Letters\\2017 v.58 p.3139-3142.pdf |
Grafting of (3-chloropropyl)-trimethoxy silane on halloysite nanotubes surface / A. M. Abu El-Soad, G. Lazzara, A. V. Pestov [et al.] // Applied sciences. - 2021. - Vol. 11, № 12. - Ст. 5534 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): GRAFTING -- HALLOYSITE NANOTUBES -- CPTMS Аннотация: Modified halloysite nanotubes (HNTs-Cl) were synthesized by a coupling reaction with (3-chloropropyl) trimethoxysilane (CPTMS). The incorporation of chloro-silane onto HNTs surface creates HNTs-Cl, which has great chemical activity and is considered a good candidate as an active site that reacts with other active molecules in order to create new materials with great applications in chemical engineering and nanotechnology. The value of this work lies in the fact that improving the degree of grafting of chloro-silane onto the HNT’s surface has been accomplished by incorporation of HNTs with CPTMS under different experimental conditions. Many parameters, such as the dispersing media, the molar ratio of HNTs/CPTMS/H2O, refluxing time, and the type of catalyst were studied. The greatest degree of grafting was accomplished by using toluene as a medium for the grafting process, with a molar ratio of HNTs/CPTMS/H2O of 1:1:3, and a refluxing time of 4 h. The addition of 7.169 mmol of triethylamine (Et3N) and 25.97 mmol of ammonium hydroxide (NH4OH) led to an increase in the degree of grafting of CPTMS onto the HNT’s surface. |
Azolyl pyrimidines-synthesis and antimicrobial activity / N. H. Basha, T. Rekha, V. Padmavathi [et al.] // AIP conference proceedings. - 2022. - Vol. 2390. - Ст. 020006 Рубрики: ЗДРАВООХРАНЕНИЕ. МЕДИЦИНСКИЕ НАУКИ ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CHEMICAL COMPOUNDS -- PHARMACEUTICALS -- ANTIMICROBIALS Аннотация: Amide unit is a privileged structural motif and is a constituent of proteins, natural products and pharmaceuticals. Amongst different heterocyclic scaffolds, azoles and pyrimidines are the prominent entities in pharmaceutical arena. The biopotency of these heterocycles have triggered to synthesize a variety of heteroaromatics – azoles linked with pyridines by amino acetamide group. The target molecules-azolylaminoacetamidopyrimidines were prepared by the reaction of methyl azolylglycinate with pyrimidinyl-2-amine in the presence of DMAP and triethylamine in dichloromethane under ultrasonication. The lead molecules were evaluated for antimicrobial activity. Nitro substituted 2-((4-(4-chlorofuran-2-yl)thiazole-2-yl)amino)-N-(4,6-diphenylpyrimidin-2-yl)acetamide (9c) displayed excellent antibacterial activity against B. subtilis greater than the standard drug Chloramphenicol. However, 9c and nitro substituted 2-((4-(4-chlorofuran-2-yl)-1H-imidazol-2-yl)amino)-N-(4,6-diphenylpyrimidin-2-yl)acetamide (10c) showed antifungal activity on A. niger greater than the standard drug Ketoconazole. |
Abnormal push-pull benzo[4,5]imidazo[1,2-a][1,2,3]triazolo[4,5-e]pyrimidine fluorophores in planarized intramolecular charge transfer (PLICT) state: Synthesis, photophysical studies and theoretical calculations / O. S. Taniya, V. V. Fedotov, L. K. Sadieva [et al.] // Dyes and Pigments. - 2022. - Vol. 204. - Ст. 110405 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The combination of excellent luminescence with high solvent polarity effect and aggregation induced emission (AIE) is an ideal combination for creating fluorophores/probes with high microenvironmental sensitivity. However, many push-pull chromophores of the D−A type in common intramolecular charge transfer (ICT) state with a significant solvatochromic effect and AIE activity, have poor luminescent properties. Herein, to overcome this problem by using reactions of nucleophilic aromatic hydrogen substitution (SNH), we have designed a series of novel 4-heteroaryl-substituted 2-aryl-2H-benzo[4,5]imidazo[1,2-a][1,2,3]triazolo[4,5-e]pyrimidine fluorophores possessing a planarized intramolecular charge transfer (PLICT) state. All these fluorophores exhibited high luminescence quantum yields (up to 60%) and large Stokes shift values of up to 7459 cm−1. Among them, the fluorophore 4h was found to exhibit the most pronounced positive solvatochromic effect and the probe 4f exhibited the most pronounced aggregation induced emission characteristics. This AIE behavior was further confirmed by means of time-resolved fluorescence lifetime measurements as well as DFT-assisted geometry optimization studies. In the presence of trifluoroacetic acid (TFA) compound 4h exhibited a well-pronounced acidochromism via visible color change from yellow-green to orange which returned to the original yellow-green solution after the addition of triethylamine (TEA). The Stern-Volmer constant for the probe 4h towards TFA was 38 M−1. Finally, for the compounds 4f, g, h theoretical calculations in the ground and excited states in different solvents were carried out to confirm the PLICT process. Based on all above the herein reported PLICT fluorophores 4a-h can be successfully applied as biological probes and optical switches. |