K 81 Krasnov, V. P. Diastereoselective substitution of halogen in 4-halogeno-N-phtalil-L-glutamates [Text] / V. P. Krasnov, M. A. Koroleva // Amino Acids. - 1993. - Vol. 5, N 1. - P125 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
Н 88 Нуклеофильное замещение галогена в 4-галогенпроизводных глутаминовой кислоты. Сообщение 2. Влияние структуры нуклеофила-ариламина [] = Nucleophilic-substitution of halogen in 4-halogenated derivatives of glutamic-acid. 2.Structural effects of arylamine as nucleophile / В. П. Краснов, М. А. Королева, Н. Г. Евстигнеева, И. А. Низова // Изв. АН. Сер. Химическая. - 1995. - N 4. - С. 656-659 . - ISSN 0002-3353 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
К 78 Краснов, В. П. Нуклеофильное замещение в 4-галогенпроизводных глутаминовой кислоты. Сообщ. 1. Влияние растворителя [] = Nucleophilic-substitution of halogen in 4-halogenated derivatives of clutamic-acid. / В. П. Краснов, М. А. Королева // Изв. АН. Сер. Химическая. - 1995. - N 4. - С. 652-655 . - ISSN 0002-3353 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
К 78 Краснов, В. П. Нуклеофильное замещение галогена в 4-галдогенпроизводных глутаминовой кислоты. Сообщение 3. Влияние высокого давления на стереохимический результат реакции [] = Nucleophilic substitution of halogen in 4-halo derivatives of glutamic acid. 3. High pressure effect on the stereochemical result of the reaction / В. П. Краснов, М. А. Королева, Г. Л. Русинов // Изв. АН. Сер. Химическая. - 1996. - N 3. - С. 583-585 . - ISSN 0002-3353 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
C 47 Charushin, V. N. Nucleophilic aromatic substitution of hydrogen and related reactions [Electronic resource] / V. N. Charushin, O. N. Chupakhin // Mendeleev Communications. - 2007. - Vol. 17, № 5. - P249-254 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The classical concept of nucleophilic aromatic substitution (SNAripso) has been complemented with a new synthetic methodology (SNH), enabling one to build new carbon–carbon C(sp2)–C(sp3), C(sp2)–C(sp2) and C(sp2)–C(sp) or carbon–heteroatom C(sp2)–X (X is O, N, P, S, halogen) bonds through nucleophilic displacement of hydrogen in an aromatic ring. \\\\Expert2\\nbo\\Mendeleev Communications\\2007, v.17, p.249.pdf |
N 10 N-alkylation of chitosan by beta-halopropionic acids in the presence of various acceptors [Text] / A. V. Pestov, Yu. A. Skorik, G. Kogan, Yu. G. Yatluk // Journal of Applied Polymer Science . - 2008. - Vol. 108, № 1. - P119-127 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: N-carboxyethylation of chitosan by -halopropionic acids in the presence of various proton and halogen ion acceptors was investigated. It has been observed that carboxyethylation of chitosan in aqueous medium is accompanied by the by-processes of hydrolysis and dehydrohalogenation of the -halopropionic acids yielding -hydroxypropionic acid, bis(2-carbox-yethyl) ether, and acrylic acid. Degree of carboxyethyl substitution (DS) of chitosan and the relative rates of the by-processes varied significantly depending on the conditions used and nature of the proton or halogen ion acceptor. At carboxyethylation of chitosan with the alkaline -bromopropionates, the DS increased in the order Cs+ Rb- K+ sim; Na+ Li-. |
H 19 Halogenation of Fluorinated 1,3-Dicarbonyl and 1,3,5-Tricarbonyl Compounds [Text] : доклад, тезисы доклада / D. V. Sevenard [и др.] // 18th ISFC international Symposium on Fluorine Chemistry. Bremen, 30th Jul.-4 Aug. 2006 г. : Final Program. Abstracts. - Bremen, 2006. - P271 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): HALOGEN -- HALOGENATION AGENTS |
K 81 Krasnov, V. P. Nucleophilic substitution of halogen in 4-halo derivatives of glutamic acid 3. High pressure effect on the stereochemical result of the reaction [Electronic resource] / V. P. Krasnov, M. A. Koroleva, G. L. Rusinov // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1996. - Vol. 45, № 3. - P543-544 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Reactions of diastereomeric dialkyl N-phthaloyl-4-haloglutamates withpara-anisidine were studied at high pressure, and an additional confirmation of the exactS N2 mechanism of the reactions was obtained. Quantitative parameters of the relative reactivity of the diastereomers were found in various solvents, which made it possible to perform the desired synthesis of products of diastereomeric substitution. kg]Key words kw]glutamic acid kw]diastereoselectivity kw]nucleophilic substitution kw]reaction rate constant kw]high pressure. \\\\Expert2\\nbo\\Russian Chemical Bulletin\\1996, 45 (3), 543.pdf |
K 81 Krasnov, V. P. Nucleophilic-substitution of halogen in 4-halogenated derivatives of glutamic-acid. 1. Solvent effect [Electronic resource] / V. P. Krasnov, M. A. Koroleva // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1995. - Vol. 44, № 4. - P631-634 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): GLUTAMIC ACID -- DIASTEREOSELECTIVITY -- NUCLEOPHILIC SUBSTITUTION -- RATE CONSTANT -- SOLVENT EFFECT Аннотация: The reaction of nucleophilic substitution of bromine by p-anisidine in dimethyl (2S,4S)- and (2S,4R)-N-phthaloyl-4-bromoglutamates proceeds according to the S(N)2 mechanism. The relative reactivity of diastereomers in various solvents was studied. \\\\Expert2\\nbo\\Russian Chemical Bulletin\\1995, 44 (4), 631.pdf |
N 91 Nucleophilic-substitution of halogen in 4-halogenated derivatives of glutamic-acid. 2. Structural effects of arylamine as nucleophile [Electronic resource] / V. P. Krasnov, M. A. Koroleva, N. G. Evstigneeva, I. A. Nizova // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1995. - Vol. 44, № 4. - P635-638 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): GLUTAMIC ACID -- DIASTEREOSELECTIVITY -- NUCLEOPHILIC SUBSTITUTION -- RATE CONSTANT -- ARYLAMINE Аннотация: Kinetics of nucleophilic substitution of halogen in diastereomeric dimethyl 4-bromo- and 4-iodoglutamates with ortho-, meta-, and para-substituted anilines was studied by HPLC. The threo-diastereomers of the halogenated derivatives react 3-5 times faster than the erythro ones. The structure of the transition state is discussed. \\\\Expert2\\nbo\\Russian Chemical Bulletin\\1995, 44 (4), 635.pdf |
C 53 Chloromethyl-, dichloromethyl-, and trichloromethyl-1,2,4-triazines and their 4-oxides: method for the synthesis and tele-substitution reactions with C-nucleophiles [Electronic resource] / D. N. Kozhevnikov, N. N. Kataeva, V. L. Rusinov, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 6. - P1295-1300 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A simple procedure was developed for the synthesis of 1,2,4-triazines and their 4-oxides containing the ClCH2, Cl2CH, or CCl3 group at position 3 by cyclization of 2-aryl-2-hydrazono-1-oximinoethanes with the corresponding chloroacetonitriles. The reaction pathway depends on the number of halogen atoms in the acetonitrile used. The reactions with trichloroacetonitrile, monochloroacetonitrile, and dichloroacetonitrile afford 3-trichloromethyl-1,2,4-triazines, 3-chloromethyl-1,2,4-triazine 4-oxides, and a mixture of the corresponding dichloromethyltriazines and their 4-oxides, respectively. The reactions of 3-trichloromethyl-1,2,4-triazines with indoles and phenols are accompanied by tele-substitution with elimination of halogen from the trichloromethyl group to give 5-indolyl- (or 5-hydroxyphenyl)-3-dichloromethyl-1,2,4-triazines \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (6), 1295-1300.pdf |
S 98 Synthesis of the (2S,4S)-stereoisomers of 4-(indol-1-yl) and 4-arylamino derivatives of 5-oxoproline, proline, and 2-hydroxymethylpyrrolidine / A. Yu. Vigorov, I. A. Nizova, K. E. Shalunova, A. N. Grishakov, L. Sh. Sadretdinova, I. N. Ganebnuikh, M. A. Ezhikova, M. I. Kodess // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2011. - Vol.60, №5. - С. 873-881 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 4-AMINOPROLINE -- 4-AMINOPROLINE -- INDOLE Аннотация: Nucleophilic substitution of the halogen atom in dimethyl (S)-4-bromoglutamate followed by removal of the protecting groups and closure of a lactam ring afforded (2S,4S)-4-(indolin-1-yl)-5-oxoproline. The indoline fragment was oxidized into the indole fragment to give (2S,4S)-4-(indol-1-yl)-5-oxoproline; reduction of the carbonyl groups with BH3 yielded (2S,4S)-4-(indol-1-yl)prolines and (2S,4S)-2-hydroxymethyl-4-(indol-1-yl)pyrrolidines. Reduction of (2S,4S)-4-arylamino-5-oxoprolines with BH3 to the corresponding (2S,4S)-4-arylaminoprolines and (2S,4S)-4-arylamino-2-hydroxymethylpyrrolidines was studied \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2011, 60 (5), 873-881.pdf |
A 10 A single crystal X-ray study of the products of halogen mercury cyclization of 8-allylthioquinoline / P. A. Slepukhin, V. I. Batalov, D. G. Kim, V. N. Charushin // Journal of Structural Chemistry. - 2012. - Vol.53, №1. - С. 145-150 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 8-ALLYLTHIOQUINOLINE -- X-RAY DIFFRACTION -- HALOGEN Аннотация: The reaction products of 8-allylthioquinoline with mercury halides are studied by single crystal X-ray diffraction. It is shown that the products are organomercury derivatives of salts of 2,3-dihydro[1,4]-thiazino[2,3,4-ij]quinoliniuim \\\\Expert2\\nbo\\Journal of Structural Chemistry\\2012, V. 53, N 1, p.145-150.pdf |
L 79 Lipunova, G. N. Fluorinated Quinolines: Synthesis, Properties and Applications / G. N. Lipunova, E. V. Nosova, V. N. Charushin // Fluorine in Heterocyclic Chemistry : Издательство "Springer", 2014. - Vol. 2. - С. 59-109. - Bibliogr. : p. 108-109 (158 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): fLUORINATED QUINOLINES -- SYNTHETIC METHODS -- CYCLOADDITION REACTIONS Аннотация: The data on the chemistry of fluorinated quinolines available in the literature of the last 10–15 years are presented. A variety of synthetic methods exploiting cyclization and cycloaddition reactions, displacements of halogen atoms or the diaza group, as well as direct fluorinations have been considered. Novel approaches to functionalization of polyfluorinated quinolines, including nucleophilic displacement of fluorine atoms, cross-coupling reactions, and synthesis on the basis of organometallic compounds are discussed. Selected representative examples of fluoroquinolines exhibiting a remarkable biological activity or those quinolines which have already found their applications in medicine will also be discussed in the text. The bibliography |
T 98 Two Approaches in the Synthesis of Planar Chiral Azinylferrocenes [Electronic resource] / I. A. Utepova, O. N. Chupakhin, P. O. Serebrennikova, A. A Musikhina, V. N. Charushin // Journal of Organic Chemistry. - 2014. - Vol. 79, № 18. - С. 8659-8667. - Bibliogr. : p. 8666-8667 (34 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CHIRAL AZINYLFERROCENES -- CROSS-COUPLING REACTION -- HALOGENATED AZINES Аннотация: Two synthetic routes to the chiral azinylferrocenes (CAFs) 5 and 15, key intermediates for the synthesis of new enantiomerically enriched P,N-ligands, have been compared. The first approach is based on the palladium-catalyzed cross-coupling reaction of halogenated azines with organozinc derivatives of ferrocenes (the Negishi reaction). The second approach exploits a new synthetic methodology, which provides a shorter pathway, through the direct C–H functionalization of aromatics by the C–C coupling of halogen-free (hetero)arenes with lithium ferrocenes bearing stereogenic C and S atoms. The palladium complexes of P,N-ligands have been used as catalysts for the Tsuji–Trost reaction, which proceeds with high enantioselectivity to give allylic substitution products in good yields. \\\\expert2\\nbo\\Journal of Organic Chemistry\\2014, v.79, p.8659.pdf |
C 57 Chupakhin, O. N. Atom- and step-economical nucleophilic arylation of azaaromatics via electrochemical oxidative cross C–C coupling reactions / O. N. Chupakhin, A. V. Shchepochkin, V. N. Charushin // Green Chemistry. - 2017. - Vol. 19, № 13. - P2931-2935 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The synthesis of asymmetrical bi(het)aryls through direct functionalization of the C(sp2)–H bond in azaaromatics with fragments of (hetero)aromatic nucleophiles has first been carried out under electrochemical oxidative conditions. This versatile method for C–C bond formation between two aryl fragments can be realized under very mild potential-controlled oxidative conditions, and it does require neither incorporation of any halogen atoms or other leaving groups, nor the use of metal catalysts. The use of the electrochemical SHN methodology for modification of azaaromatic compounds has first been demonstrated. \\\\Expert2\\NBO\\Green Chemistry\\2017 v.19 p.2931-2935.pdf |
Chupakhin, O. N. Application of electrochemical oxidative methods in the C(SP2)–H functionalization of heterocyclic compounds / O. N. Chupakhin, A. V. Shchepochkin, V. N. Charushin // Advances in heterocyclic chemistry. - 2020. - Т. 131. - P1-47 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): C-H FUNCTIONALIZATION -- ELECTROCHEMICAL OXIDATION -- GREEN CHEMISTRY -- OCDC -- SN H REACTIONS Аннотация: New atom-economic and environmentally friendly processes should replace the traditional ways of building C–C, C–N, C–O, C–P, C–S bonds, which are usually based on the replacement of a halogen atom, and, therefore, required the preliminary modification of substrates, and the use of aggressive reagents, harsh conditions or expensive catalysts. In recent years, the direct metal-free functionalization of the C(sp2)–H bond, which provides the most efficient and low-waste pathway for molecular transformation, has attracted increasing attention. However, these transformations usually require stoichiometric amounts of chemical oxidizing agents. The modern world and its sustainable development trends are forcing the chemical industry to improve in an environmentally friendly direction and meet the requirements of “green chemistry.” In this regard, the use of electrochemical methods is extremely important. Electrochemical anodic oxidation is an ideal option for the replacement of chemical oxidizers in C–H functionalization reactions. The data on the main electrochemical methods and approaches used for the direct functionalization of the C(sp2)–H bond in heterocyclic compounds are classified and summarized in this paper. |
Korolyova, M. A. Theoretical study of the stereoselectivity in the reaction of 4-haloglutamic acid derivatives with arylamines / M. A. Korolyova, A. Yu. Vigorov, V. P. Krasnov // Russian chemical bulletin. - 2022. - Vol. 71, № 6. - P1135-1142 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Diastereoselective nucleophilic substitution reaction of halogen in dimethyl (2S,4RS)-4-bromo- and 4-iodo-N-phthaloylglutamates with arylamines was studied within the framework of the electron density functional theory. According to calculations, the stereoselectivity of the substitution reaction with respect to (2S,4S)-isomers of 4-arylamino derivatives is determined not only by the steric hindrances in the transition state leading to minor (2S,4R)-diastereomers, but also by the stabilization of the corresponding initial reagents complex due to stacking interactions of the aromatic fragments of reagents. |