О-42 1-Alkyl-1,2,4-triazinium ylides as 1,3-dipoles in a cycloaddition reaction with diethyl acetylenedicarboxylate [Electronic resource] / O. N. Chupakhin, B. V. Rudakov, S. G. Alexeev, S. V. Shorshnev, V. N. Charushin // Mendeleev Communications. - 1992. - N 3. - P85-86 . - ISSN 0959-9436 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 1-АЛКИЛ-1.2.4-ТРИАЗИНИЛИДЫ -- ИЛИДЫ -- ДИПОЛИ -- 1.3-ДИПОЛИ -- ЦИКЛОПРИСОЕДИНЕНИЕ -- ДИЭТИЛАЦЕТИЛЕНДИКАРБОКСИЛАТ -- ДЕПРОТОНАЦИЯ -- 1-АЛКИЛ-5-ФЕНИЛ-1.2.4-ТРИАЗИНА СОЛИ -- триэтиламины -- АЗОМЕТИНИЛИДЫ -- ЦИКЛОПРИСОЕДИНЕНИЕ ДИПОЛЯРНОЕ -- ДИПОЛЯРНОЕ ЦИКЛОПРИСОЕДИНЕНИЕ -- ПИРРОЛО[2.1-F]1.2.4-ТРИАЗИНЫ -- СОЛИ -- ОРГАНИЧЕСКАЯ ХИМИЯ -- ХИМИЯ ОРГАНИЧЕСКАЯ Аннотация: Deprotonation of 1-alkyl-5-phenyl-1,2,4-triazinium salts by triathylamine results in the formation of azomethyne ylides which undergo a 1,3-dipolar cycloaddition reaction with diethyl acetylenedicarboxylate to yield pyrrolo[2,1-f]1,2,4-triazines \\\\expert2\\nbo\\Mendeleev Communications\\1992, v.2, N 3. p.85-86.pdf |
O-57 One-Step Heterylation at the Upper Rim of Calix[4]arene with 1,2,4-Triazin-5(2H)-ones [Electronic resource] / D. G. Beresnev, N. A. Itsikson, O. N. Chupakhin, V. N. Charushin, M. I. Kodess, A. I. Butakov, G. L. Rusinov, Yu. Yu. Morzherin, A. I. Konovalov, I. S. Antipin // Journal of Organic Chemistry. - 2006. - Vol. 71, № 21. - P8272-8275 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A convenient way to modify calix[4]arenes based on the direct C-C coupling reaction of their phenol moiety with 1,2,4-triazines has been advanced, and the ability of modified calixarenes to provide transport of La3+ and Ga3+ cations through organic membranes has been examined. ?? \\\\Expert2\\nbo\\Journal of Organic Chemistry\\2006, v.71, N 21, p.8272.pdf |
A 10 A simple one pot synthesis of condensed 1,2,4-triazines by using the tandem AN-SNipso and SNH-SNipso reactions [Text] / O. N. Chupakhin, G. L. Rusinov, D. G. Beresnev, V. N. Charushin, H. Neunhoeffer // Journal of Heterocyclic Chemistry. - 2001. - Т. 38, № 4. - P901-907 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A new synthetic approach to condensed 1,2,4-triazines based on using the tandem AN-SNipso and SNH-SNipso reactions has been developed. 5-Methoxy-3-penyl-l,2,4 1,2,4-triazine and its N1-methyl quaternary salt were found to react with C,N-, C,O- and N,N?-bifunctional nucleophiles (m-phenylenediamine, resorcinol, semicarbazide and ureas) into triazacarbazoles, benzofuro[2,3-e][1,2,4]-triazines, and 6-azapurine derivatives. In all cases nucleophiles attack first the unsubstituted C-6 carbon of the triazine ring, while the final stage is replacement of the methoxy group affording cyclization products. \\\\Cserver\\dist\\НБО\\Электронная библиотека_Библиогр1\\Journal of Heterocyclic Chemistry\\2001.v.38.p.901.Chupachin.pdf |
P 93 Protolytic equilibrium of the isomeric phenyl-1,2,4-triazines [Electronic resource] / I. V. Khabibulina, A.P. Volovodenko, R. E. Trifonov, G. V. Yashukova, N. N. Mochul`skaya, V. N. Charushin, G. L. Rusinov, D. G. Beresnev, N. A. Itsikson, V. A. Ostrovskii // Chemistry of Heterocyclic Compounds. - 2003. - Vol. 39, № 5. - P616-623 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The protonation constants for the first and second stages (pK BH+, pKBH2+) of a series of 1,2,4-triazines with a phenyl substituent at various positions in the ring were determined in aqueous solution by a spectrophotometric method. The values of the basicity constants characterizing the first protonation of the heterocycles investigated was in the range of acidity of the medium of pH 3.5 to H0 -2, and the second from H0 -7.3 to H0 -8.7. The position of the phenyl substituent proved to have a significant effect on the size of pK BH+. According to the results of ab initio calculations using HF/6-31G** for the heterocycles investigated the 1H+ form is thermodynamically most stable among the monocations, with the exception of 6-phenyl-1,2,4-triazine for which the existence of the monocation in the 1H+ and 2H+ forms are equally probable. In the case of the dications of all the triazines the 2,4-H,H2+ tautomer is the most preferred. The aromaticity of the 1,2,4-triazine ring is changed insignificantly on mono- and diprotonation. \\\\Expert2\\nbo\\Chemistry of Heterocyclic Compounds\\2003, v.39, N 5, p.616. .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 |
U 88 Use of tandem AN-AN reactions for the synthesis of thiazolo[4,5-e]-1,2,4-triazines [Electronic resource] / V. N. Charushin, N. N. Mochul`skaya, A. A. Andreiko, M. I. Kodess, O. N. Chupakhin // Mendeleev Communications. - 2002. - Vol. 12, № 1. - P28-29 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 3-Aryl-1,2,4-triazines react with thioamides in acetic anhydride to produce thiazolo[4,5-e]-1,2,4-triazine derivatives and this reaction represents a new method for the fusion of thiazole and 1,2,4-triazine rings based on the nucleophilic ortho-diaddition type (AN-AN) cyclization reactions?????? \\\\expert2\\nbo\\Mendeleev Communications\\2002, v.12, N 1. p.28.pdf |
A 48 Aminovinyl ketones and aminovinyl esters as C---C---N building blocks for the synthesis of 1H-pyrrolo[3,2-e]1,2,4-triazines [Text] / V. N. Charushin, N. N. Mochul`skaya, A. A. Andreiko, T. I. Filyakova, M. I. Kodess, O. N. Chupakhin // Tetrahedron Letters. - 2003. - Vol. 44, № 11. - P2421-2424. - Bibliogr. : p. 2424 (16 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 5,6-Unsubstituted-3-aryl-1,2,4-triazines were found to react with aminovinyl ketones and aminovinyl esters in acetic anhydride to form derivatives of 3a,4,7,7a-tetrahydro-1H-pyrrolo[3,2-e]1,2,4-triazines in good yields???? \\\\Expert2\\nbo\\Tetrahedron Letters\\2003. v.44. p.2421.pdf |
U 88 Use of the tandem An-An reactions for the synthesis of condensed 1,2,4-triazines [Text] : доклад, тезисы доклада / V. N. Charushin, N. N. Mochul`skaya, A. A. Andreiko, M. I. Kodess, O. N. Chupakhin // XXth European Colloquium on Heterocyclic Chemistry, Stockholm,Sweden, 18-21 Aug. 2002 г. - Stockholm, 2002. - PA:8 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
C 47 Charushin, V. N. 1,2,4-Triazines and their Benzo Derivatives [] : монография / V. N. Charushin, V. L. Rusinov, O. N. Chupakhin // Comprehensive Heterocyclic Chemistry III : Elsevier : Oxford, 2008. - Vol. 9. - 95-196. Рубрики: ХИМИЧЕСКИЕ НАУКИ |
S 98 Synthesis of pyridines from 1,2,4-triazines under high pressure [Electronic resource] / M. M. Krayushkin, I. P. Sedishev, V. N. Yarovenko, I. V. Zavarzin, S. K. Kotovskaya, D. N. Kozhevnikov, V. N. Charushin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2008. - Vol. 44, № 3. - P407-411 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A procedure has been proposed for the synthesis of pyridines from 1,2,4-triazine derivatives and bicyclo[2.2.1]hepta-2,5-diene under high pressure in the presence of lithium perchlorate as catalyst \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2008, 44 (3), 407.pdf |
A 60 Annelation of the thiazole ring to 1,2,4-triazines by tandem AN—AN or SNH—SNH reactions [Electronic resource] / N. N. Mochul`skaya, A. A. Andreiko, M. I. Kodess, E. B. Vasil'eva, V. I. Filyakova, A. T. Gubaidullin, I. A. Litvinov, O. G. Sinyashin, G. G. Aleksandrov, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 6. - P1279-1289 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reactions of 3-aryl-1,2,4-triazines with aromatic thioamides and 4-arylthiosemicarbazides in acetic anhydride at room temperature afforded cyclic products of the tandem nucleophilic addition reactions, viz., tetrahydrothiazolo[4,5-e]-annelated 1,2,4-triazines, in good yields. The latter underwent aromatization in the presence of potassium permanganate \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (6), 1279.pdf |
T 19 Tandem AN—AN reactions in the synthesis of 1H-pyrrolo[3,2-e]-1,2,4-triazines and products of their oxidative transformations [Electronic resource] / V. N. Charushin, N. N. Mochul`skaya, A. A. Andreiko, M. I. Kodess, I. A. Litvinov, O. G. Sinyashin, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2003. - Vol. 52, № 8. - P1740-1749 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reactions of 3-aryl-1,2,4-triazines with -aminovinyl ketones or ethyl -aminocrotonates in acetic anhydride at room temperature afforded cyclic products of the tandem nucleophilic addition, viz., 3a,4,7,7a-tetrahydro-1H-pyrrolo[3,2-e]-1,2,4-triazines, in good yields. Under oxidative conditions, the latter compounds underwent the pyrrole-ring opening under the action of potassium permanganate to form the corresponding triazinones and were transformed into thriazolyl-substituted pyridines under the action of selenious acid \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2003, 52 (8), 1740.pdf |
A 99 Azolo[5,1-c]-1,2,4-triazines as a new class of antiviral compounds [Electronic resource] / V. L. Rusinov, E. N. Ulomskii, V. N. Charushin, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2008. - Vol. 57, № 5. - P985-1014 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Synthetic methods, reactivity, and the properties of a new class of antiviral compounds, pyrazolo-, imidazo-, 1,2,4-triazolo[5,1-c]-1,2,4-triazinones, tetrazolo[5,1-b]-1,2,4-triazinones, and azoloannulated amino-1,2,4-triazines having structural similarity with biogenic purines and capable of mimicking them in metabolic processes are considered \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2008, 57 (5), 985.pdf |
S 98 Synthesis of new meso-substituted heterocyclic calix[4]arenes via SN H approach [Electronic resource] / M. V. Varaksin, I. A. Utepova, G. N. Chupakhin, V. N. Charushin // Macroheterocycles . - 2013. - Vol.6, №4. - С. 308-314. - Bibliogr. : p. 313-314 (42 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): AZINES -- C-C COUPLING -- CALIX[4]ARENES Аннотация: An effective synthetic approach to heterocyclic derivatives of meso-substituted calixarenes has been suggested by using the SN H methodology based on the direct, non-catalyzed by transition metals, C-C coupling of 1,2,4-triazines with the lithium salts of tetramethoxycalix[4]arenes \\\\expert2\\NBO\\Macroheterocycles\\2013.6.4.308-314.pdf |
B 45 Berezin, M. V. C-H Functionalisation of 1,2,4,-Triazines/ The Treatment of 3-R-1,2,4-Triazines with C-nucleophiles / M. V. Berezin, G. L. Rusinov, V. N. Charushin // Уральский научный форум "Современные проблемы органической химии". XVII Молодежная школа-конф. по органической химии, Екатернинбург, 8-12 июня 2014 г. : сб. тез. - Екатеринбург, 2014. - С. 116 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 1,2,4-TRIAZHIES -- GLC-MS |
R 95 Rusinov, V. L. Fluorinated Triazines / V. L. Rusinov, E. V. Nosova, V. N. Charushin // Fluorine in Heterocyclic Chemistry : Издательство "Springer", 2014. - Vol. 2. - С. 673-716. - Bibliogr. : p. 715-716 (119 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SYNTHETIC ROUTES -- 1,2,3-TRIAZINES -- 1,2,4-TRIAZINES -- 1,3,5-TRIAZINES Аннотация: In this chapter data on structure, synthetic routes, reactivity of derivatives of 1,2,3-triazines, 1,2,4-triazines and 1,3,5-triazines − bearing one or several fluorine atoms in heterocyclic ring as well as trifluoromethyl substituted triazines are considered and analyzed, and also their certain representatives are discussed |
D 62 Direct fusion of a triazine to a pyrazine ring. Synthesis of derivatives of [1,2,4]triazino[5,6-b]quinoxaline [Electronic resource] / V. N. Charushin, V. G. Baklykov, O. N. Chupakhin, L. M. Naumova // Chemistry of Heterocyclic Compounds. - 1984. - Vol. 20, № 9. - P1057-1058. - Bibliogr. : p. 1058 (2 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): TRIAZINES -- PYRAZINES \\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\1984, v.20, N 9, p. 1057.pdf |
A 32 Alekseev, S. G. New type of transformation of a 1,2,4-triazine ring to pyrazine derivatives (Letter) [Electronic resource] / S. G. Alekseev, V. N. Charushin, O. N. Chupakhin // Chemistry of Heterocyclic Compounds. - 1987. - Vol. 23, № 2. - С. 238-239. - Bibliogr. : p. 239 (6 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRAZINE DERIVATIVES -- 1,2,4-TRIAZINES \\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\1987, v.23, N 2, p. 238.pdf |
C 98 Cyclizations of 1,2,4-triazinium salts with bifunctional nucleophiles - a new route to condensed 1,2,4-triazines [Electronic resource] / S. G. Alexeev, V. N. Charushin, O. N. Chupakhin, G. G. Alexandrov // Tetrahedron Letters. - 1988. - Vol. 29, № 12. - С. 1431-1434. - Bibliogr. : p. 1434 (6 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 1,2,4-TRIAZINIUM SALTS -- AMIDES -- NUCLEOPHILES Аннотация: The reaction of 1,2,4-triazinium salts with amides of acetoacetic acid yielding 1,4,4a,5,7,7a-hexahydro-6H-pyrrolo[3,2-e]-1,2,4-triazin-6-ones exemplifies the first direct annelation to the 1,2,4-triazine ring based on the diaddition of bifunctional nucleophiles at C-5 and C-6. \\\\expert2\\nbo\\Tetrahedron Letters\\1988, v 29, p.1431.pdf |
B 39 Behavior of Monocyclic 1,2,4-Triazines in Reactions with C-, N-, O-, and S-Nucleophiles [Electronic resource] / V. N. Charushin, S. G. Alexeev, O. N. Chupakhin, H. C. Van der Plas // Advances in Heterocyclic Chemistry. - 1989. - Vol. 46 (C). - С. 73-142. - Bibliogr. : p. 135-142 (200 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 1,2,4-TRIAZINES -- NITROGEN-CONTAINING HETEROCYCLES Аннотация: Among the six-membered nitrogen-containing heterocycles the 1,2,4-triazines have attracted the attention of chemists for a long time. This is due to the fact that many 1,2,4-triazine derivatives are biologically active and are used in medicine and agriculture. Moreover, 1,2,4-triazines are of chemical interest. They proved to be very susceptible to attack by all kinds of nucleophiles, leading to the addition, and subsequently either substitution or cyclization, and ring transformation. This continuing and lively interest in this area of heterocyclic chemistry has produced a great number of publications and patent applications. This chapter concentrates on the behavior of monocyclic 1,2,4-triazines in reactions with C-, N-, 0-, and S-nucleophiles, because the important features of general character established for simple 1,2,4-triazines can evidently be applied to other derivatives including condensed 1,2,4-triazines. \\\\expert2\\nbo\\Advances in Heterocyclic Chemistry\\1988. V. 46 (C). P. 73-142.pdf |