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1.

Вид документа : Статья из сборника (однотомник)
Шифр издания : 54
Автор(ы) : Chupakhin O. N., Krasnov V. P., Demin A. M., Levit G. L., Kodess M. I.
Заглавие : 1H NMR evidence for 5(4H)-oxazolones formation and racemization : доклад, тезисы доклада
Место публикации : XXth European Colloquium on Heterocyclic Chemistry, Stockholm,Sweden, 18-21 Aug. 2002 г. - Stockholm, 2002. - С. C:2
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
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2.

Вид документа : Статья из журнала
Шифр издания : 54
Автор(ы) : Filyakova T. I., Saloutin V. I., Zapevalov A. Ya., Slepukhin P. A., Kodess M. I., Saloutin V. I.
Заглавие : 2,3-Epoxyperfluoro-2-methylpentane in reactions with urea and thiourea [Electronic resource]
Место публикации : Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2011. - Vol. 47, № 5. - С. 650-658: рис., табл.
Систем. требования: http://www.springerlink.com/content/l221n3xn6v8t4n87/fulltext.pdf
Примечания : Bibliogr. : p. 658 (24 ref.). - 1.11.2011 г.
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: 2,3-Epoxyperfluoro-2-methylpentane reacts with thiourea in protic (methanol, 2-propanol) and aprotic (dioxane) solvents, and also with urea in acetonitrile affording unexpected products: 1-(2,2,3,3,3-pentafluoropropionyl)-2-(2,2,2-trifluoro-1-trifluoro-methylethyl)isothiourea, and 1-(2,2,3,3,3-pentafluoropropionyl)-3-(2,2,2-trifluoro-1-trifluoro-methylethyl)urea respectively that result from the rearrangement of the intermediately formed ketone in the process of the intramolecular “haloform” cleavage. At the same time in dioxane the 2,3-epoxyperfluoro-2-methylpentane reacts with urea with the formation of a heterocyclic compound, 2-amino-4-pentafluoroethyl-5,5-bis(trifluoromethyl)-4,5-dihydrooxazol-4-ol. From 1-(2,2,3,3,3-pentafluoropropionyl)-2-(2,2,2-trifluoro-1-trifluoromethylethyl)isothiourea and Cu(OAc)2 a stable fluorine-containing chelate complex was obtained
\\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2011, 47 (5), 650-658.pdf
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3.

Вид документа : Статья из журнала
Шифр издания : 54
Автор(ы) : Korotaev V.Yu., Skorik Yu.A., Barkov A. Yu., Kodess M. I., Zapevalov A. Ya.
Заглавие : 3,3,3-Trifluoro-N-(3-trifluoromethylphenyl)-1,2-propanediamine and its N-mono-and N,N-dicarboxyethyl derivatives: synthesis, protolytic and complexation properties [Electronic resource]
Место публикации : Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2005. - Vol. 54, № 11. - С. 2545-2549
Систем. требования: http://www.springerlink.com/content/5372448026312478/fulltext.pdf
Примечания : 26.10.2011 г.
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: 3,3,3-Trifluoro-N-(3-trifluoromethylphenyl)-1,2-propanediamine (5) was synthesized by the reaction of 2-diazo-1,1,1-trifluoro-3-nitropropane or 3,3,3-trifluoro-1-nitropropene with 3-aminobenzotrifluoride followed by the reduction of the nitro group. The Michael 1,4-addition of diamine 5 to acrylic acid occurs only at the N(1) atom and affords N-mono-or N,N-dicarboxyethyl derivatives 6 and 7, depending on the reactant ratio. Protolytic equilibria 5–7 in aqueous solutions were studied by pH-potentiometry and UV spectroscopy. Only the aliphatic amino group can be protonated in an aqueous solution, while the aromatic amino group remains unprotonated even in 12 M HCl. The stability constants of transition metal (Cu2+, Ni2+, Zn2+) complexes with ligands 5–7 were determined by pH-potentiometric titration. The stability of the complexes and selectivity of the ligands toward Cu2+ ions increase with an increase in the number of N-carboxyethyl groups
\\\\Expert2\\nbo\\Russian Chemical Bulletin\\2005, 54 (11), 2545.pdf
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4.

Вид документа : Статья из журнала
Шифр издания : 54
Автор(ы) : Belskaia N. P., Bakulev V. A., Deryabina T. G., Subbotina J.O., Kodess M. I.
Заглавие : 3-Alkylsulfanyl-2-arylazo-3-(pyrrolidin-1-yl)-acrylonitriles as masked 1,3-dipoles
Место публикации : Tetrahedron. - 2009. - Vol. 65, № 36. - С. 7662-7672
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Reaction of 3-alkylsulfanyl-2-arylazo-3-(pyrrolidin-1-yl)acrylonitriles with maleimides, dimethyl maleate and dimethylacetylene dicarboxylate were carried out to give octahydro-pyrrolo[3,4-a]pyrrolizin-4-ylidenes, hexahydro-pyrrolizines and 6,7-dihydro-5H-pyrrolizines. The formation of the synthesized compounds is explained by a 1,3-dipolar cycloaddition of an in situ generated azomethine ylide. The mechanisms of the formation of these active intermediates were discussed with the aid of density functional theory methods with the B3LYP functional 6-31G+ calculations using the STQN method and chemical experiments
\\\\Expert2\\nbo\\Tetrahedron\\2009, v. 65, p. 7662.pdf
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5.

Вид документа : Статья из журнала
Шифр издания : 54
Автор(ы) : Kotovskaya S. K., Romanova S. A., Charushin V. N., Kodess M. I., Chupakhin O. N.
Заглавие : 5(6)-Fluoro-6(5)-R-benzofuroxans: synthesis and NMR 1H, 13C and 19F studies
Место публикации : Journal of Fluorine Chemistry. - 2004. - Vol. 125, № 3. - С. 421-428: ил.
Примечания : Библиогр.: с. 428 (14 ref.)
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: 5(6)-Fluoro-6(5)-substituted benzofuroxans were obtained by the reactions of 5,6-difluorobenzofuroxan with a number of nucleophiles, such as alkylamines, cycloalkylimines, sodium azide and sodium alkoxides. The features of tautomerism in the series of asymmetrical 5(6)-fluorobenzofuroxans in acetone solutions have been studied by 1H, 13C and 19F NMR.????
\\\\Expert2\\nbo\\Journal of Fluorine Chemistry\\2004, v.125, p.421.pdf
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6.

Вид документа : Статья из журнала
Шифр издания : 54/A 10
Автор(ы) : Gruzdev D.A., Chulakov E.N., Levit G. L., Ezhikova M. A., Kodess M. I., Krasnov V. P.
Заглавие : A comparative study on the acylative kinetic resolution of racemic fluorinated and non-fluorinated 2-methyl-1,2,3,4-tetrahydroquinolines and 3,4-dihydro-3-methyl-2H-[1,4]benzoxazines
Место публикации : Tetrahedron: Asymmetry . - 2013. - Vol.24, №19. - С. 1240-1246
Примечания : Bibliogr. : p. 1246 (21 ref.)
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): racemic fluorinated --1,2,3,4-tetrahydroquinolines--benzoxazines
Аннотация: The acylative kinetic resolution of racemic 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline, 7,8-difluoro-3,4-dihydro-3-methyl-2H-[1,4]benzoxazine, and their non-fluorinated analogues with (S)-naproxen and N-phthaloyl-(S)-amino acyl chlorides has been carried out. It has been shown that the presence of fluorine atoms in the aromatic fragment of a heterocyclic amine results in the increasing stereoselectivity of acylation with (S)-naproxen acyl chloride and in a decrease in the efficiency of acylative kinetic resolution using N-phthaloyl-(S)-amino acyl chlorides. A method for the preparation of enantiopure (S)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (ee 99%) was developed
\\\\expert2\\NBO\\Tetrahedron Asymmetry\\2013, in Press, Corr. Proof, 4 Sept.pdf
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7.

Вид документа : Статья из журнала
Шифр издания : 54/A 10
Автор(ы) : Boguslavskii A. M., Ponizovskii M. G., Kodess M. I., Charushin V. N.
Заглавие : A new methodology of annelation of five- and seven-membered heterocycles to quinoxalines [Electronic resource]
Место публикации : Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2003. - Vol. 52, № 10. - С. 2175-2184
Систем. требования: http://www.springerlink.com/content/w155l1p01678555g/fulltext.pdf
Примечания : 24.10.2011
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Pyrazolo[3,4-b]-, isoxazolo[4,5-b]-, benzo[2,3]-1,4-diazepino-, and benzo[2,3]-1,4-oxazepinoquinoxalines were prepared by reactions of 2-quinoxalinecarboxaldehyde with 1,2-N,N-, 1,2-N,O and 1,4-N,N- and 1,4-N,O-dinucleophiles
\\\\Expert2\\nbo\\Russian Chemical Bulletin\\2003, 52 (10), 2175.pdf
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8.

Вид документа : Статья из журнала
Шифр издания : 54/A 10
Автор(ы) : Belskaia N. P., Deryabina T. G., Koksharov A.V., Kodess M. I., Lebedev A.T., Bakulev V. A.
Заглавие : A novel approach to fused 1,2,4-triazines by intramolecular cyclization of 1,2-diaza-1,3-butadienes bearing allyl(propargyl)sulfanyl and cyclic tert-amino groups
Место публикации : Tetrahedron Letters. - 2007. - Vol. 48, № 52. - С. 9128-9131
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: 3-Allyl- and 3-prop-1-ynylsulfanyl-2-arylazo-3-cycloalkylamino-acrylonitriles undergo cyclization under mild conditions to afford the novel heterocyclic systems 1,4,6,7,8,8a-hexahydropyrrolo[2,1-c][1,2,4]-triazine-4-thione, 1,4,6,7,9,9a-hexahydro-[1,4]oxazino[3,4-c][1,2,4]triazine and 1,6,7,8,9,9a-hexahydro-4H-pyrido[2,1-c][1,2,4]triazine via a number of consecutive pericyclic reactions
\\\\Expert2\\nbo\\Tetrahedron Letters\\2007, v. 48, p.9128.pdf
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9.

Вид документа : Статья из журнала
Шифр издания : 54/A 10
Автор(ы) : Saloutina L. V., Zapevalov A. Ya., Kodess M. I., Saloutin V. I., Chupakhin O. N.
Заглавие : A route to fluorocontaining 1,3-thiazolines via internal polyfluorooxiranes [Electronic resource]
Место публикации : Mendeleev Communications. - 1999. - N 6. - С. 231-232. - ISSN 0959-9436. - ISSN 0959-9436
Систем. требования: http://www.sciencedirect.com/science/article/pii/S0959943699710527
Примечания : 10.10.2011
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The reaction of internal fluoroolefin oxides with thiourea results in 2-amino-5-fluoro-4-hydroxy-4,5-di(polyfluoroalkyl)-1,3-thiazolines, providing a route to an unknown type of fluorine-containing thiazolines with two fluoroalkyl substituents
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10.

Вид документа : Статья из журнала
Шифр издания : 54/A 10
Автор(ы) : Saloutina L. V., Zapevalov A. Ya., Saloutin V. I., Slepukhin P. A., Kodess M. I., Kirichenko V. E., Pervova M. G., Chupakhin O. N.
Заглавие : A route to fluorocontaining N,S-heterocycles via octafluoro-2,3-epoxybutane
Место публикации : Journal of Fluorine Chemistry. - 2007. - Vol. 128, № 7. - С. 769-778
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The reaction of octafluoro-2,3-epoxybutane 1 with 2-aminothiophenol gave three kinds of novel fluorocontaining N,S-heterocyclic compounds depending on the solvent nature: 2,3-bis(trifluoromethyl)-3,4-dihydro-2H-1,4-benzothiazin-2-ol 2, 2-trifluoromethyl-2-[1-(2-aminophenylthio)-2,2,2-trifluoroethyl]-1,3-benzothiazolidine 6 and 5a,11a-bis(trifluoromethyl)-5a,6,11a,12-tetrahydro-5,11-dithia-6,12-diazanaphthacene 5. Use of the toluene, dioxane, tetrahydrofuran, acetonitrile and dimethoxyethane gave the unexpected dihydrobenzothiazine 2 (RS,SR RR,SS) in good to moderate yields. In dimethylsulfoxide and N,N-dimethylacetamide, unusual cyclization occurred resulting in benzothiazolidine 6 (RS,SR/RR,SS 1:1) in moderate yields. Formation of minor 1,1,1,3,4,4,4-heptafluoro-3-(2-aminophenylthio)-2,2-dihydroxybutane 4 which was converted into bis(benzothiazine) 5 was observed in all solvents tested with the exception of toluene and dioxane. The molecular structure of the RS,SR-diastereomer of dihydrobenzothiazine 2, bis(benzothiazine) 5 and the RS,SR-diastereomer of benzothiazolidine 6 has been established by X-ray crystallography.
\\\\Expert2\\nbo\\Journal of Fluorine Chemistry\\2007, v.128. p.769.pdf
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11.

Вид документа : Статья из журнала
Шифр издания : 54/A 10
Автор(ы) : Korotaev V.Yu., Sosnovskikh V. Ya., Kutyashev I. B., Barkov A. Yu., Matochkina E. G., Kodess M. I.
Заглавие : A simple and convenient synthesis of 4-methyl-3-nitro-2-trihalomethyl-2H-chromenes from N-unsubstituted imines of 2-hydroxyacetophenones and trichloro(trifluoro)ethylidene nitromethanes
Место публикации : Tetrahedron. - 2008. - Vol. 64, № 22. - С. 5055-5060
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The reaction of N-unsubstituted imines of 2-hydroxyacetophenones with trichloro(trifluoro)ethylidene nitromethanes in the presence of DABCO proceeds via tandem oxa-Michael/aza-Henry additions (in dichloromethane) or aza-Michael addition (in benzene) to give 4-methyl-3-nitro-2-trichloro(trifluoro)methyl-2H-chromenes or 1,1,1-trichloro(trifluoro)-3-nitro-N-[1-(2-hydroxyaryl)ethylidene]propan-2-amines, respectively????
\\\\Expert2\\nbo\\Tetrahedron\\2008, v. 64, N22, p. 5050.pdf
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12.

Вид документа : Статья из журнала
Шифр издания : 54/A 10
Автор(ы) : Korotaev V.Yu., Sosnovskikh V. Ya., Barkov A. Yu., Slepukhin P. A., Ezhikova M. A., Kodess M. I., Shklyaev Yu. V.
Заглавие : A simple synthesis of the pentacyclic lamellarin skeleton from 3-nitro-2-(trifluoromethyl)-2H-chromenes and 1-methyl(benzyl)-3,4-dihydroisoquinolines
Место публикации : Tetrahedron. - 2011. - Vol. 67, № 45. - С. 8685-8698
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): lamellarin alkaloids--isoquinoline derivatives--heterocyclic system
Аннотация: The basic structural framework of lamellarin alkaloids, 8,9-dihydro-6H-chromeno[4?,3?:4,5]pyrrolo[2,1-a]isoquinoline derivatives, has been obtained in good yields via Grob synthesis between 3-nitro-2-(trifluoromethyl)-2H-chromenes and 1-methyl-3,4-dihydroisoquinolines in refluxing isobutanol. In the case of 1-benzyl-3,4-dihydroisoquinolines, a dynamic NMR effect was observed in the 1H and 19F NMR spectra of the products as a result of restricted rotation about the single bond linking the benzene ring and the heterocyclic system. When the reaction was carried out with 3-nitro-2-(trichloromethyl)-2H-chromenes in toluene at room temperature, only Michael adducts, as a mixture of two diastereomers, were isolated.??????--------------------------------------------------------------------------------??
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13.

Вид документа : Статья из журнала
Шифр издания : 54/A 18
Автор(ы) : Levit G. L., Demin A. M., Kodess M. I., Ezhikova M. A., Sadretdinova L. Sh., Ol'shevskaya V. A., Kalinin V. N., Krasnov V. P., Charushin V. N.
Заглавие : Acidic hydrolysis of N-acyl-1-substituted 3-amino-1,2-dicarba-closo-dodecaboranes
Место публикации : Journal of Organometallic Chemistry. - 2005. - Vol. 690, № 11. - С. 2783-2786
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Acidic hydrolysis of N-acyl 1-methyl- and 1-phenyl-3-amino-1,2-dicarba-closo-dodecaboranes has been studied. It has been shown that acidic hydrolysis of diastereomeric amides of 1-methyl-3-amino-1,2-dicarba-closo-dodecaborane results in the partial racemization of the target 3-amino-1-methylcarborane. Under the similar conditions, the hydrolysis of N-acyl-3-amino-1-phenyl-1,2-dicarba-closo-dodecaboranes resulted in amide bond cleavage accompanied by simultaneous deboronation with the removal of boron atom at position 6 of carborane cage and formation of 7,8-dicarba-nido-undecaborane derivative according to 11B and 1H NMR spectroscopy.
\\\\Expert2\\nbo\\Journal of Organometallic Chemistry\\2005, v. 690, p.2783.pdf
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14.

Вид документа : Статья из журнала
Шифр издания : 54/A 19
Автор(ы) : Denisova A.V., Bakulev V. A., Dehaen W., Toppet S., Van Meerlent L., Kodess M. I.
Заглавие : Acylation and Carbamoylation of 2-Hydrazinothiazole Derivatives. Identification of Isomeric Structures [Electronic resource]
Место публикации : Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2005. - Vol. 41, № 4. - С. 584-590
Систем. требования: http://www.springerlink.com/content/u82t64215k1317tk/fulltext.pdf
Примечания : 1.11.2011 г.
ББК : 54
Предметные 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
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15.

Вид документа : Статья из журнала
Шифр издания : 54/A 19
Автор(ы) : Gruzdev D.A., Levit G. L., Krasnov V. P., Chulakov E.N., Sadretdinova L. Sh., Grishakov A. N., Ezhikova M. A., Kodess M. I., Charushin V. N.
Заглавие : Acylative kinetic resolution of racemic amines using N-phthaloyl-(S)-amino acyl chlorides
Место публикации : Tetrahedron: Asymmetry . - 2010. - Vol. 21, № 8. - С. 936-942
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: A comparative study of the kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and 2,3-dihydro-3-methyl-4H-1,4-benzoxazine using N-phthaloyl-(S)-amino acyl chlorides as chiral acylating agents is described. Temperature and solvent effects on the stereochemical features have been examined. It has been found that N-phthaloyl-(S)-phenylalanyl and N-phthaloyl-(S)-2-phenylglycyl chlorides bearing aromatic substituents close to the stereogenic centre are more stereoselective acylating agents than N-phthaloyl-(S)-alanyl chloride. For the preparative kinetic resolution of racemic amines N-phthaloyl-(S)-phenylalanyl chloride proved to be the most appropriate chiral acylating agent
\\\\Expert2\\nbo\\Tetrahedron Asymmetry\\2010, v. 21, p.936.pdf
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16.

Вид документа : Статья из сборника (однотомник)
Шифр издания : 54/A 19
Автор(ы) : Krasnov V. P., Levit G. L., Kozhevnikov D. N., Kodess M. I., Gruzdev D.A., Chulakov E.N., Charushin V. N.
Заглавие : Acylative kinetic resolution of racemic amines with profens and amino acids derivatives
Место публикации : International Congress on Organic Chemistry, dedicated to the 150-th anniversary of the Butlerov's Theory of Chemical Structure of Organic Compounds, Kazan, September 18-23, 2001 : book of abstr. - Kazan, 2011. - С. 85
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): kinetic resolution--s-amines--racemic amines
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17.

Вид документа : Статья из журнала
Шифр издания : 54/A 19
Автор(ы) : Vakarov S. A., Gruzdev D.A., Chulakov E.N., Sadretdinova L. Sh., Tumashov A. A., Pervova M. G., Ezhikova M. A., Kodess M. I., Levit G. L., Krasnov V. P., Charushin V. N.
Заглавие : Acylative kinetic resolution of racemic heterocyclic amines with (R)-2-phenoxypropionyl chloride
Место публикации : Tetrahedron: Asymmetry . - 2016. - Vol. 27, № 24. - С. 1231-1237
Примечания : Bibliogr. : p. 1236-1237 (15 ref.)
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): heterocyclic amines --benzoxazines-- 2-methylindoline--kinetic resolution
Аннотация: The acylative kinetic resolution of racemic heterocyclic amines such as 3,4-dihydro-3-methyl-2H-[1,4]benzoxazines, 3,4-dihydro-3-methyl-2H-[1,4]benzothiazine, 2-methyl-1,2,3,4-tetrahydro-quinolines and 2-methylindoline with enantiopure (R)-2-phenoxypropionyl chloride has been studied. It has been found that acylation of 3,4-dihydro-3-methyl-2H-[1,4]benzothiazine proceeds with the best stereoselectively when compared with other racemic amines. An efficient method for the preparation of (S)-3,4-dihydro-3-methyl-2H-[1,4]benzothiazine (99.4% ee) via a kinetic resolution protocol was developed. The possibility of recycling (R)-2-phenoxypropionic acid has been demonstrated.
\\\\expert2\\NBO\\Tetrahedron Asymmetry\\2016, v. 27, p.1231.pdf
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18.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Gruzdev D.A., Vakarov S. A., Korolyova M. A., Tumashov A. A., Chulakov E.N., Ezhikova M. A., Kodess M. I., Levit G. L., Krasnov V. P., Bartashevich E. V.
Заглавие : Acylative kinetic resolution of racemic methyl-substituted cyclic alkylamines with 2,5-dioxopyrrolidin-1-yl (R)-2-phenoxypropanoate
Место публикации : Organic & biomolecular chemistry. - 2022. - Vol. 20, № 4. - С. 862-869
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The diastereoselective acylation of a number of racemic methyl-substituted cyclic alkylamines with active esters of 2-phenoxypropanoic acid was studied in detail. The ester of (R)-2-phenoxypropanoic acid and N-hydroxysuccinimide was found to be the most selective agent. The highest stereoselectivity was observed in the kinetic resolution of racemic 2-methylpiperidine in toluene at −40 °C (selectivity factor s = 73) with the predominant formation of (R,R)-amide (93.7% de). To explain the observed stereoselectivity, DFT modelling of the transition states in the reactions of the title acylating agent with 2-methylpiperidine and 2-methylpyrrolidine was performed. The calculated values were in good agreement with experimental data. It has been demonstrated that the acylation proceeds via a concerted mechanism, in which the addition of an amine occurs simultaneously with the elimination of the hydroxysuccinimide fragment. The high stereoselectivity of the (R,R)-amide formation is largely ensured by the lower steric hindrances in the transition states as compared to the formation of (R,S)-amide.
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19.

Вид документа : Статья из журнала
Шифр издания : 54/A 48
Автор(ы) : Belykh D.V., Tarabukina I.S., Gruzdev D.A., Kodess M. I., Kutchin A.V.
Заглавие : Aminomethylation of chlorophyll a derivatives using bis(N,N-dimethylamino) methane
Место публикации : Journal of Porphyrins and Phthalocyanines. - 2009. - Vol. 13, № 7-8. - С. 949-956
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Bis(N,N-dimethylamino)methane has been shown to be a convenient reagent for the aminomethylation of chlorophyll a derivatives. Methylpheophorbide a (in enol form) and chlorin e6 13-amides were aminomethylated with bis(N,N-dimethylamino)methane. Reactivity of methylpheophorbide a exo-ring and chlorin e6 13-amides vinyl group were shown to be different. Selective methylpheophorbide a exo-ring aminomethylation was realized and isomerization of the exo-ring aminomethylation product with rhodochlorin 15-acrylic derivative formation was studied. The action of bis(N,N- dimethylamino)-methane in the presence of weak acid has been shown to be a simple and effective synthetic procedure to obtain a new chlorin e6 derivative with two N,N-dimethylaminomethyl substituents in the vinyl group. The aminomethylation products' high yields, the simplicity of the procedure, the use of metal-free chlorines and the possible synthesis of new compounds, were found to be the main advantages of using bis(N,N-dimethylamino)methane as an aminomethylation reagent in chlorophyll a derivatives' chemistry
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20.

Вид документа : Статья из журнала
Шифр издания : 54/A 48
Автор(ы) : Charushin V. N., Mochul`skaya N. N., Andreiko A. A., Filyakova T. I., Kodess M. I., Chupakhin O. N.
Заглавие : Aminovinyl ketones and aminovinyl esters as C---C---N building blocks for the synthesis of 1H-pyrrolo[3,2-e]1,2,4-triazines
Место публикации : Tetrahedron Letters. - 2003. - Vol. 44, № 11. - С. 2421-2424
Примечания : Bibliogr. : p. 2424 (16 ref.)
ББК : 54
Предметные 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
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