S 98 Synthesis of trifluoroalkyl- and fluoroaryl-substituted 4,5-dihydro-1H-1,2,4-triazole-5-thiones [Electronic resource] / E. B. Vasil'eva, D. V. Sevenard, O. G. Khomutov, O. A. Kuznetsova, N. S. Karpenko, V. I. Filyakova // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2004. - Vol. 40, № 6. - P874-878. - Библиогр. : с. 878 (8 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Reactions of 4-(4-fluorophenyl)-, 4-(4-trifluoromethoxyphenyl)-, 4-(3,4-difluorophenyl)-, 4-(4-trifluoromethylphenyl)-, 4-piperidino-, and 4-(3-pyridyl)thiosemicarbazides with esters gave the corresponding 3,4-disubstituted 4,5-dihydro-1H-1,2,4-triazole-5-thiones and their S-alkyl derivatives. Analogous reactions with methyl 2,2,3,3,4,4,5,5-octafluoropentanoate and 2,2,3,3,4,4,5,5-octafluoropentanenitrile afforded, respectively, the acylation and addition products. \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2004, 40 (6), 874.pdf |
F 70 Fluoro-containing heterocycles: Part XIII. Fluoro-containing derivatives of thiazolo[3,2-a]-, benzothiazolo[3,2-a]-, and benzimidazo[3,2-a]quinazolinones [Electronic resource] / E. V. Nosova, G. N. Lipunova, A. A. Laeva, V. N. Charushin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2005. - Vol. 41, № 11. - P1671-1677. - Библиогр. : с. 1677 (22 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Reactions of 2-aminothiazole, derivatives of 2-aminobenzothiazole and 2-aminobenzoimidazole with polyfluorobenzoyl chlorides gave rise to acylation products that at heating in the diphenyl ether formed fluoro-containing derivatives of thiazolo[3,2- a]-, benzothiazolo[3,2- a]-, and benzimidazo[3,2- a]quinazolinone. \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2005, 41 (11), 1671.pdf |
K 46 Kinetic resolution of 1-methyl- and 1-phenyl-3-amino-1,2-dicarba-closo-dodecaboranes via acylation with chiral acyl chlorides [Electronic resource] / G. L. Levit, V. P. Krasnov, A. M. Demin, M. I. Kodess, L. Sh. Sadretdinova, T. V. Matveeva, V. A. Ol'shevskaya, V. N. Kalinin, O. N. Chupakhin, V. N. Charushin // Mendeleev Communications. - 2004. - Vol. 14, № 6. - P293-295 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A study of the kinetic resolution of racemic 1-substituted 3-amino-1,2-dicarba-closo-dodecaboranes by chiral acyl chlorides has shown that N-tosyl-(S)-prolyl and N-phthaloyl-(S)-alaninyl chlorides are more efficient resolving agents than (S)-naproxen chloride. \\\\Expert2\\nbo\\Mendeleev Communications\\2004, v.14, p.293.pdf |
N 10 N-Phthaloyl-(S)-alanyl chloride as a chiral resolving agent for the kinetic resolution of heterocyclic amines [Text] / V. P. Krasnov, G. L. Levit, M. I. Kodess, V. N. Charushin, O. N. Chupakhin // Tetrahedron: Asymmetry . - 2004. - Vol. 15, № 5. - P859-862 : ил. - Библиогр.: с. 862 (7 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): HETEROCYCLIC AMINES -- CHLORIDE -- KINETIC RESOLUTION Аннотация: Acylation of heterocyclic amines with N-phthaloyl-(S)-alanyl chloride under kinetic resolution conditions resulted in the predominant formation of (S,S)-amides. The diastereoselectivity of resolution depended heavily on the structure of the resolved amine.???? \\\\Expert2\\nbo\\Tetrahedron Asymmetry\\2004, v.15, p.859.pdf |
D 62 Direct modification of benzoannelated crown ethers with 1,2,4-triazin-5(2H)-one moieties [Text] / G. L. Rusinov, D. G. Beresnev, N. A. Itsikson, O. N. Chupakhin // Heterocycles. - 2001. - Т. 55, № 12. - P2349-2359 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A convenient method for one-step coupling of benzoannelated crown ethers with 1,2,4-triazinones based on the reaction of nucleophilic addition to unsubstituted carbon atom of the triazine ring has been worked out. It has been shown that the reaction of 3-substituted 1,2,4-triazin-5(2H)-ones (1) with benzocrown ethers (benzo-12-crown-4, benzo-15-crown-5, benzo-18-crown-6) in the presence of acetic or trifluoroacetic anhydride is accompanied by acylation of triazine ring and results in formation of 3-(1-acyl-5-oxo-1,4,5,6-tetrahydro-1,2,4-triazin-6-yl)benzocrown ethers (7-12). The latters were converted to 3-(5-oxo-2,5-dihydro-1,2,4-triazin-6-yl)benzocrown ethers (18-20) using two alternative routes: the elimination of acetic or trifluoroacetaldehyde or the deacylation followed by the oxidation of the 1,4,5,6-tetrahydro derivatives (13-15). |
F 70 Fluoroaryl containing beta,beta-dioxoesters in the synthesis of fluorobenzopyran-4(2)-ones [Text] / S. P. Kisil', Ya. V. Burgart, V. I. Saloutin, O. N. Chupakhin // Journal of Fluorine Chemistry. - 2001. - Vol. 108, № 2. - P125-131 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Fluoroaryl containing ?,??-dioxoesters and their copper(II) chelates have been prepared by acylation of ethyl acetoacetate with 2,6-dimethoxy-3,4,5-trifluorobenzoyl, 2-methoxy-3,4,5,6-tetrafluorobenzoyl and pentafluorobenzoyl chlorides. Cyclization of these ?,??-dioxoesters leads to formation of substituted fluorochromones. Depending on conditions, 2-methyl-5-methoxy-6,7,8-trifluoro-3-ethoxycarbonylchromone hydrolyzed to 5-hydroxy-2-methyl-6,7,8-trifluorochromone or 5-hydroxy-2-methyl-6,7,8-trifluorochromone-3-carboxylic acid. The same chromone reacts with morpholine to form a seven-substituted product and ammonium hydroxide to give 3-iminoacetyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin. Hydrolysis of the latter affords 3-acetyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin. Ethyl-2-(2,6-dimethoxy-3,4,5-trifluorobenzoyl)-3-oxobutanoates undergoes ketone-splitting to 1-(2,6-dimethoxy-3,4,5-trifluorophenyl)-1,3-butandione???? |
A 10 A route to ethyl alfa-pentafluorobenzoyl-beta-oxobutanoate via its copper(II) chelate [Text] / Ya. V. Burgart, S. P. Kisil', V. I. Saloutin, O. N. Chupakhin // Mendeleev Communications. - 2001. - Vol. 11, № 2. - P76 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Ethyl 2-pentafluorobenzoyl-3-oxobutanoate has been prepared by the acylation of ethyl acetoacetate with pentafluorobenzoyl chloride via a copper(II) chelate |
E 54 Enantiomers of 3-amino-1-methyl-1,2-dicarba-closo-dodecaborane [Text] / V. P. Krasnov, G. L. Levit, V. N. Charushin, M. I. Kodess, V. N. Kalinin, O. N. Chupakhin // Tetrahedron: Asymmetry . - 2002. - Vol. 13, № 16. - P1833-1835. - Bibliogr. : p. 1835 (6 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The enantiomers of 3-amino-1-methyl-1,2-dicarba-closo-dodecaborane were prepared by means of resolution of the racemic mixture via acylation by (S)-naproxen chloride followed by separation and subsequent acid hydrolysis of each of the diastereoisomeric amides. Partial racemization of enantiomeric 3-aminocarboranes was observed during acid hydrolysis \\\\Expert2\\nbo\\Tetrahedron Asymmetry\\2002, v.13, p.1833.pdf |
K 46 Kinetic resolution of (±)-2-methyl-1,2,3,4-tetrahydroquinoline and (±)-2-methylindoline [Electronic resource] / V. P. Krasnov, G. L. Levit, I. N. Andreeva, A. N. Grishakov, V. N. Charushin, O. N. Chupakhin // Mendeleev Communications. - 2002. - Vol. 12, № 1. - P27-28 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The acylation of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and 2-methylindoline by (S)-naproxen acyl chloride resulted in their kinetic resolution with the predominant formation of (S,S)-diastereoisomeric amides (de 78–76%), recrystallisation of which followed by acid hydrolysis gave individual (S)-isomers of heterocyclic amines???? \\\\expert2\\nbo\\Mendeleev Communications\\2002, v.12, N 1. p.27.pdf |
K 46 Kinetic resolution of (±)-2,3-dihydro-3-methyl-4H-1,4-benzoxazine, (±)-2-methyl-1,2,3,4-tetrahydroquinoline and (±)-2-methylindoline using N-tosyl-(S)-prolyl chloride [Text] / V. P. Krasnov, G. L. Levit, I. M. Bukrina, I. N. Andreeva, L. Sh. Sadretdinova, M. A. Koroleva, M. I. Kodess, V. N. Charushin, O. N. Chupakhin // Tetrahedron: Asymmetry . - 2003. - Vol. 14, № 14. - P1985-1988. - Bibliogr. : p. 1988 (6 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Acylation of racemic 2,3-dihydro-3-methyl-4H-1,4-benzoxazine, 2-methyl-1,2,3,4-tetrahydroquinoline and 2-methylindoline with N-tosyl-(S)-prolyl chloride resulted in their kinetic resolution with the predominant formation of (R,S)-diastereoisomeric amides, des being 80, 66 and 38%, respectively. Recrystallisation of the amides followed by acid hydrolysis gave individual (R)-enantiomers of heterocyclic amines \\\\Expert2\\nbo\\Tetrahedron Asymmetry\\2003, v.14, p.1985.pdf |
S 98 Synthesis of 8-R-9c-alkyl-1-aryl-2-benzyl-1-hydroxy-1,2,9b,9c-tetrahydro-5-oxa-2-aza-cyclopenta[2,3]cyclopropa[1,2-a]naphthalene-3,4-diones and reaction thereof with acetic anhydride [Text] / V. V. Shchepin, P. S. Silaichev, A. R. Racitin, M. I. Kodess // Tetrahedron Letters. - 2006. - Vol. 47, № 4. - P557-560 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reaction of zinc enolates synthesized from 1-aryl-2,2-dibromoalkanones and zinc with 6-R-2-oxochromene-3-carboxylic acid N-benzylamide affords 8-R-9c-alkyl-1-aryl-2-benzyl-1-hydroxy-1,2,9b,9c-tetrahydro-5-oxa-2-aza-cyclopenta[2,3]cyclopropa[1,2-a]naphthalene-3,4-diones. Acylation of these compounds is accompanied by an unexpected rearrangement producing a sole geometrical isomer of 4?-alkyl-5?-aryl-1?-benzyl-3,4,2?,3?-tetrahydro-2,2?-dioxospiro[chroman-3,3?-pyrrol]-4-yl acetates \\\\Expert2\\nbo\\Tetrahedron Letters\\2006, v. 47, p.557.pdf |
P 93 Prokhorov, A. M. Direct introduction of acetylene moieties into azines by S(N)H methodology [Text] / A. M. Prokhorov, M. Makosza, O. N. Chupakhin // Tetrahedron Letters. - 2009. - Vol. 50, № 13. - P1444-1446 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The N-oxides of azines 1a–g react with lithium and/or potassium acetylides to give the corresponding ethynylazines 2a–g. Reaction with lithium acetylide requires subsequent acylation of the intermediate anionic adduct for rearomatization whereas in the case of potassium acetylide, auto-aromatization takes place?? \\\\Expert2\\nbo\\Tetrahedron Letters\\2009, V. 50, N 13, p.1444.pdf |
K 49 Kisil', S. P. New Fluoroaryl-containing beta,beta'-Dioxoesters in the Synthesis of Fluorobenzopyran-2(4)-ones [Electronic resource] / S. P. Kisil', Ya. V. Burgart, V. I. Saloutin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2001. - Vol. 37, № 10. - P1455-1462 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: For the first time were obtained ethyl 2-(2-methoxy-3,4,5,6-tetrafluorobenzoyl)-3-oxobutanoate and ethyl 2-pentafluorobenzoyl-3-oxobutanoate and their copper chelates. The compounds were prepared by acylation of ethyl acetoacetate with 2-methoxy-3,4,5,6-tetrafluoro- and pentafluorobenzoyl chlorides. Cyclization of these ,'-dioxoesters afforded substituted chromones. 2-Methyl-5-methoxy-6,7,8-trifluoro-3-ethoxycarbonylchromone hydrolyzes depending on reaction conditions either to 5-hydroxy-2-methyl-6,7,8-trifluorochromone or to 5-hydroxy-2-methyl-6,7,8-trifluorochromone-3-carboxylic acid. Reaction with morpholine provided 7-substituted product, and with aqueous ammonia as a result of rearrangement forms 3-acetimidoyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin. Hydrolysis of the latter yields 3-acetyl-4-hydroxy-5-methoxy-6,7,8-triflu \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2001, 37 (10), 1455.pdf |
S 98 Synthesis of ethyl 3-oxo-2-(3,4,5-trifluoro-2,6-dimethoxybenzoyl)butyrate [Electronic resource] / S. P. Kisil', M. I. Kodess, Ya. V. Burgart, V. I. Saloutin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2000. - Vol. 49, № 6. - P1090-1092 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Ethyl acetoacetate was acylated with 3,4,5-trifluoro-2,6-dimethoxybenzoyl chloride to give, for the first time, ethyl 3-oxo-2-(3,4,5-trifluoro-2,6-dimethoxybenzoyl)butyrate and its copper chelate. The title compound was used for the synthesis of 6,7,8-trifluoro-5-hydroxy-2-methylchromone, 1-(3,4,5-trifluoro-2,6-dimethoxyphenyl)butane-1,3-dione, and its copper chelate \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2000, 49 (6), 1090.pdf |
S 98 Synthesis of 4-acyl(alkoxycarbonyl)-5-fluoroalkyl-3,5-dihydroxyfuran-2(5H)-ones [Electronic resource] / M. V. Pryadeina, Ya. V. Burgart, K. I. Suslova, V. I. Saloutin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2002. - Vol. 51, № 9. - P1727-1730 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 4-Acyl(alkoxycarbonyl)-5-fluoroalkyl-3,5-dihydroxyfuran-2(5H)-ones were obtained for the first time by the reactions of fluoroalkyl-containing 1,3-diketones and 3-oxo esters with oxalyl chloride \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2002, 51 (9), 1727.pdf |
K 46 Kinetic resolution of heterocyclic amines by reaction with optically active acid chlorides. The effect of reaction conditions on the diastereoselectivity of acylation of (±)-3-methyl-2,3-dihydro-4H-1,4-benzoxazine [Electronic resource] / V. P. Krasnov, G. L. Levit, M. A. Koroleva, I. M. Bukrina, L. Sh. Sadretdinova, I. N. Andreeva, V. N. Charushin, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 6. - P1253-1256 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The influence of the reaction conditions (solvent, base) on the diastereoselectivity of acylation of (±)-3-methyl-2,3-dihydro-4H-1,4-benzoxazine with (S)-naproxen and N-tosyl-(S)-proline chlorides was studied. The highest diastereoselectivity was observed for the reaction carried out in benzene in the presence of aliphatic tertiary amines \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (6), 1253.pdf |
N 52 New 1,2,4-triazine-containing podands: synthesis and properties [Electronic resource] / O. N. Chupakhin, G. L. Rusinov, N. A. Itsikson, D. G. Beresnev, O. V. Fedorova, I. G. Ovchinnikova // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 10. - P2308-2313 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A method of one-step C-C coupling of 1,5-bis(2,6-dimethylphenoxy)-3-oxapentane (1a) and 1,8-bis(2,6-dimethylphenoxy)-3,6-dioxaoctane (1b) with 3-methylthio- (2) and 3-amino-1,2,4-triazine (3) and 3-aryl-1,2,4-triazin-5-one (6-8) has been described. The reaction of compounds 1a,b with compounds 2 and 3 in the presence of trifluoroacetic acid results in the addition of the dimethylphenoxy group to the unsubstituted C(5) carbon atom of the triazine ring. The reactions of triazinones 6-8 with compounds 1a,b in a mixture of trifluoroacetic acid and organic anhydrides are accompanied by the acylation of the nitrogen atom adjacent to the reaction center and affords bis[(3-R-1-acyl-5-oxo-1,4,5,6-tetrahydro-1,2,4-triazin-6-yl)-2,6-dimethylphenoxy]-3-oxapentane or -3,6-dioxaoctane. The obtained adducts can smoothly be oxidized under mild conditions to form more stable products of nucleophilic hydrogen substitution in the triazine ring. The extraction and transport of Ca2+ and Mg2+ cations through an organic membrane by the compounds synthesized are discussed. \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (10), 2308.pdf |
S 53 Shchepin, V. V. Unexpected formation of 5-aryl-1-benzyl-4-methyl-3,4,2,3-tetrahydro-2,2-dioxospiro[chroman3,3-pyrrol]-4-yl acetates at acylation of 1-aryl-2-benzyl-1-hydroxy-9c-methyl-1,2,9b,9c-tetrahydro-5-oxa-2-azacyclopenta[2,3]cyclopropa[1,2-a]naphthalene-3,4-diones with acetic anhydride [Electronic resource] / V. V. Shchepin, P. S. Silaichev, M. I. Kodess // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2006. - Vol. 42, № 5. - P778-779 Рубрики: ХИМИЧЕСКИЕ НАУКИ \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2006, 42 (5), 778.pdf |
A 19 Acylation and Carbamoylation of 2-Hydrazinothiazole Derivatives. Identification of Isomeric Structures [Electronic resource] / A. V. Denisova, V. A. Bakulev, W. Dehaen, S. Toppet, L. Van Meerlent, M. I. Kodess // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2005. - Vol. 41, № 4. - P584-590 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Acylation and carbamoylation of 2-(arylmethylidenehydrazino)- and 2-(aroylhydrazino)thiazoles was performed, and structure of the products was established \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2005, 41 (4), 584.pdf |
T 82 Transformations of 1,2,4-triazines in reactions with nucleophiles: IV. Nucleophilic substitution of hydrogen in 1,2,4-triazine 4-oxides under acylation conditions [Text] / V. L. Rusinov, D. N. Kozhevnikov, I. S. Kovalev, O. N. Chupakhin, G. G. Aleksandrov // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2000. - Vol. 36, № 7. - P1050-1060. - Bibliogr. : p. 1060 (13 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 3-SUBSTITUTED 6-PHENYL-1,2,4-TRIAZINE 4-OXIDES -- AROMATIC NUCLEOPHILES -- AUTOAROMATIZATION -- KINETIC REGIOSELECTIVITY -- THERMODYNAMIC REGIOSELECTIVITY |