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1.
Инвентарный номер: нет.
   
   K 46


   
    Kinetic resolution of racemic 6-substituted 1,2,3,4-tetrahydroquinaldines with chiral acyl chlorides. Experiment and quantum chemical simulation / E. N. Chulakov, M. A. Korolyova, L. S. Sadretdinova [et al.] // Russian chemical bulletin. - 2021. - Vol. 70, № 5. - P890-899
ББК Г
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: A comparative study of the kinetic resolution (KR) of racemic 6-substituted 2-methyl-1,2,3,4-tetrahydroquinolines with acyl chlorides of (S)-naproxen, N-phthaloyl-(S)-leucine, and (R)-O-phenyllactic acid was carried out. The selectivity factors in the KR of racemic amines with acyl chlorides of (S)-naproxen and (R)-O-phenyllactic acid were shown to be approximately the same and higher than those for the KR of N-phthaloyl-(S)-leucyl chloride. The reasons for the stereodifferentiation in the KR of racemic tetrahydroquinaldines containing groups of different electronic properties by acyl chlorides of three different chiral acids were explained using the DFT method. The conditions for stabilizing π—π interactions of aromatic fragments of the reagents, which do not occur in the same form in the transition state and lead to the minor diastereoisomeric product, are created in the transition state of the faster acylation reaction with (S)-naproxen and (R)-O-phenyllactic acyl chlorides. In the case of the KR of 2-methyl-1,2,3,4-tetrahydroquinoline and 2-methyl-6-methoxy-1,2,3,4-tetrahydroquinoline with N-phthaloyl-(S)-leucyl chloride, the acylation diastereoselectivity is determined, most likely, by conformational factors. The individual (S)-enantiomer of 2-methyl-6-methoxy-1,2,3,4-tetrahydroquinoline of high optical purity was synthesized using the KR of the racemate with (S)-naproxen acyl chloride.

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2.
Инвентарный номер: нет.
   


   
    Functionalized trifluoromethyl-containing lithium β-diketonate in the synthesis of homo- and heteronuclear complexes of rare-earth metals / Yu. S. Kudyakova, P. A. Slepukhin, I. N. Ganebnykh [и др.] // Russian Journal of Coordination Chemistry. - 2021. - Vol. 47, № 4. - P280-295
Кл.слова (ненормированные):
β-DIKETONATES -- LANTHANIDES -- 19F NMR SPECTROSCOPY -- MASS SPECTROMETRY
Аннотация: The reactions of functionalized lithium CF3-β-diketonate (LiL) with trivalent rare-earth metal salts in methanol afford homobinuclear and heterobi(tri)nuclear complexes depending on the nature of the transition metal and anion (chlorides, nitrates, and acetates). In the cases of lanthanum(III) and cerium(III), homoleptic complexes [(LnL3)2] are isolated (CIF files CCDC nos. 2031097 (Ia) and 2031102 (Ib)). The reaction of LiL with praseodymium(III) nitrate gives the new trimetallic structure [(LiPrL3)(LiL)(NO3)(H2O)2] (CIF file CCDC no. 2031103 (II)), and the replacement of nitrate by chloride gives [(PrL3)(LiL)(H2O)] (CIF file CCDC no. 2031104 (IIIa)). Regardless of the nature of the anion of the salt in the series from neodymium(III) to ytterbium(III) and yttrium(III), Ln–Li β-diketonates [(LnL3)(LiL)(solv)] (solv is H2O and MeOH) are formed, and their structures are characterized by X-ray structure analysis (CIF files CCDC nos. 2031099 (IIIb), 2031100 (IIIc), 2031098 (IVa), 2031096 (IVc), 2031094 (IVf), 2031101 (IVg), and 2031095 (IVh)). The equilibrium of the diketonate isomeric forms in a solution of deuterated dimethyl sulfoxide is studied by 19F NMR spectroscopy, and the qualitative composition of the polynuclear complexes is determined by mass spectrometry.

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3.
Инвентарный номер: нет.
   


   
    Mutual kinetic resolution of 3-methyl-3,4-dihydro-2h-1,4-benzoxazines and 2-alkoxyacyl chlorides / S. A. Vakarov, D. Gruzdev, L. S. Sadretdinova, M. I. Kodess, A. A. Tumashov, E. B. Gorbunov, G. L. Levit, V. P. Krasnov // Chemistry of Heterocyclic Compounds. - 2018. - Vol. 54, № 4. - P437-446
Рубрики: ХИМИЧЕСКИЕ НАУКИ

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4.
Инвентарный номер: нет.
   
   S 98


   
    Synthesis of Assemblies of Isoxazole and Azoles Based on 1,3-Dipolar Cycloaddition Reaction of Enamines with Nitrile Oxides = Cинтез ансамблей изоксазолов c азолами в реакции 1,3-диполярного циклоприсоединения енаминов к нитрилоксидам / I. Efimov, Yu. Shafran, N. N. Volkova, N. Beliaev, P. A. Slepukhin, V. A. Bakulev // Chemistry of Heterocyclic Compounds. - 2016. - Vol. 52, № 9. - С. 743-749. - Bibliogr. : p. 748-749 (32 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
ENAMINES -- ISOXAZOLES -- HYDROXAMOYL CHLORIDES
Аннотация: 2-(1,2,3-Thiadiazol-5-yl)enamines and 3-(1,2,3-triazol-4-yl)enaminones react with arylhydroxamoyl chlorides at room temperature with the exclusive formation of 3-aryl-4-(1,2,3-thiadiazol-5-yl)- and [4-(1,2,3-triazol-4-yl)carbonyl]isoxazoles in high yields. The proposed mechanism includes in situ generation of nitrile oxides, which participate in the (3+2)-dipolar cycloaddition reactions leading to the formation of the isoxazole ring.

\\\\expert2\\NBO\\Chemistry of Heterocyclic Compounds\\2016, v.52, N 9, p. 743-749.pdf
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5.
Инвентарный номер: нет.
   
   N 89


   
    Novel 3-acetyl-2-methyl-polyfluorochromones in reactions with amines and esters of amino acids [Electronic resource] / K. V. Shcherbakov, D. N. Bazhin, Ya. V. Burgart, V. I. Saloutin // Chemistry of Heterocyclic Compounds. - 2015. - Vol. 51, № 11/12. - С. 961-968. - Bibliogr. : p. 967-968 (21 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
AMINE -- ACYLATION -- CHROMONE
Аннотация: Novel 3-acetyl-2-methyl-polyfluoro-4Н-chromen-4-ones were obtained via one-pot acylation of acetylacetone with polyfluorobenzoyl chlorides. These chromones were shown to form N-substituted 3-amino-1-[2-hydroxy(polyfluoro)phenyl]but-2-en-1-ones in reaction with aliphatic primary amines, esters of amino acids, and aqueous ammonia via opening of the pyrone ring and deacylation

\\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\2015, v.51, N 11-12, p. 961-968.pdf
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6.
Инвентарный номер: нет.
   
   D 53


   
    Diastereoselective acylation of 3,4-dihydro-3-methyl-2H-[1,4]benzoxazines with 2-phenoxy carbonyl chlorides / S. A. Vakarov, D. A. Gruzdev, L. Sh. Sadretdinova, E. N. Chulakov, M. G. Pervova, M. A. Ezhikova, M. I. Kodess, G. L. Levit, V. P. Krasnov // Tetrahedron: Asymmetry . - 2015. - Vol. 26, № 5-6. - С. 312-319
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
CARBONYL CHLORIDES -- DIASTEREOSELECTIVE SYNTHESIS -- dIASTEREOSELECTIVE ACYLATION

\\\\expert2\\NBO\\Tetrahedron Asymmetry\\2015, v. 26, p.312.pdf
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7.
Инвентарный номер: нет.
   
   R 30


   
    Reactivity of 1,2,3-triazoles towards sulfonyl chlorides. A novel approach to 1-and 2-sulfonyl-4-azolyl-1,2,3-triazoles / T. Beryozkina, I. Efimov, W. M. F. Fabian, N. Beliaev, P. A. Slepukhin, M. L. Isenov, W. Dehaen, G. Lubec, O. S. Eltsov, Z. Fan // Tetrahedron. - 2015. - Vol. 71, № 36. - С. 6189-6195
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
1,2,3-TRIAZOLES -- SULFONYL CHLORIDES -- 2-SULFONYL-4-AZOLYL-1,2,3-TRIAZOLES

\\\\expert2\\NBO\\Tetrahedron\\2015, v. 71 , p. 6189.pdf
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8.
Инвентарный номер: нет.
   
   L 62


    Levit, G. L.
    Acylative kinetic resolution with chiral acyl chlorides as an efficient preparative approach for enantio pure heterocyclic amines / G. L. Levit, V. P. Krasnov // CHIRALITY 2014. 26-th International Symposium on Chiral Discrimination, ISCD-26, Prague, Czech Repablic, 27-30 July 2014 : book of asbstracts. - Prague, 2014. - 218 (P-099). - Bibliogr. : p. 218 (2 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
HETEROCYCLIC AMINES -- RESOLVING AGENTS -- SYNTHESIS

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9.
Инвентарный номер: нет.
   
   L 62


    Levit, G. L.
    Acylative Kinetic Resolution with Chiral Acyl Chlorides as an Efficient Preparative Approach for Enantio Pure Heterocyclic Amines / G. L. Levit, V. P. Krasnov // CHIRALITY 2014 : book of abstr., Prague, Czech Republic, 27-30 July 2014. - 2014. - P. 218 (P-099)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
CHIRAL ACYL CHLORIDES -- HETEROCYCLIC AMINES

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10.
Инвентарный номер: нет.
   
   A 10


   
    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 [Electronic resource] / D. A. Gruzdev, E. N. Chulakov, G. L. Levit, M. A. Ezhikova, M. I. Kodess, V. P. Krasnov // Tetrahedron: Asymmetry . - 2013. - Vol.24, №19. - С. 1240-1246. - Bibliogr. : p. 1246 (21 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
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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11.
Инвентарный номер: нет.
   
   A 19


   
    Acylative kinetic resolution of racemic amines with N-protected (S)-amino acyl chlorides / D. A. Gruzdev, G. L. Levit, V. P. Krasnov, V. N. Charushin // 18th European Symposium on Organic Chemistry ESOC-2013, Marseille, France, 7-12 July 2013 : book of abstracts. - Marseille (France) , 2013. - 244 (P1-184)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
RACEMIC AMINES -- CHLORIDES -- ACYLATIVE KINETIC RESOLUTION

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12.
Инвентарный номер: нет.
   
   S 98


   
    Synthesis of enantiomers of 6-nitro- and 6-amino-2-methyl-1,2,3,4-tetrahydroquinolines / D. A. Gruzdev, G. L. Levit, M. I. Kodess, V. P. Krasnov // Chemistry of Heterocyclic Compounds. - 2012. - Vol.48, №5. - С. 748-757
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
AMIDES -- DIASTEREOISOMERS -- ENANTIOMERS
Аннотация: Enantiomers of 2-methyl-6-nitro-1,2,3,4-tetrahydroquinoline have been obtained by kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline in acylation with acyl chlorides of N-protected amino acids followed by regioselective nitration of the diastereoisomeric amides and acidic hydrolysis. The introduction of a trifluoroacetyl protecting group into the position 1 of the enantio pure nitro compound followed by the reduction led to (S)-6-amino-2-methyl-1-trifluoroacetyl-1,2,3,4-tetra-hydroquinoline in a high yield

\\\\Expert2\\nbo\\Chemistry of Heterocyclic Compounds\\2012, v.48, N 5, p.748-757.pdf
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13.
Инвентарный номер: нет.
   
   N 10


   
    N-heterocyclic carbenes. IV.(1)Synthesis of symmetrical and unsymmetrical imidazolium salts with abietane moiety / V. A. Glushkov, K. A. Arapov, M. S. Kotelev, K. S. Rudowsky, K. Yu. Suponitsky, A. A. Gorbunov, O. A. Maiorova, P. A. Slepukhin // Heteroatom Chemistry. - 2012. - Vol.23, №1. - С. 5-15
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
IMIDAZOLINIUM -- 12-AMINODEHYDROABIETATE -- SALTS OF IMIDAZOLINIUM
Аннотация: Methyl 12-chloromethyl-dehydroabie-tate reacts with 1-benzyl- and 1-arylimidazoles to give unsymmetrically substituted imidazolium chlorides (1a–i), with abietane moiety. Starting from methyl 12-aminodehydroabietate, symmetrically substituted diterpene-based salts of imidazolinium (4) and imidazolium (5) were synthesized. Anion exchange afforded corresponding (1e·BF4) and (1e·PF6). The new compounds were tested as ligands for a Pd-catalyzed Suzuki-Miyaura reaction. The molecular structure of (1e) is reported

\\\\Expert2\\nbo\\Heteroatom Chemistry\\2012, V. 23, N 1, P. 5-15.pdf
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14.
Инвентарный номер: нет.
   
   G 90


    Gruzdev, D. A.
    Acylative kinetic resolution of racemic heterocyclic amines using N-phthaloyl-(S)-amino acyl chlorides with alkyl side chains / D. A. Gruzdev, G. L. Levit, V. P. Krasnov // Tetrahedron: Asymmetry . - 2012. - Vol.23. - С. 1640-1646. - Bibliogr.: p. 1645-1646 (15 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
HETEROCYCLIC AMINES -- RACEMIC AMINES -- ACYL CHLORIDES
Аннотация: A comparative study of the acylative kinetic resolution of racemic 2-methyl-1,2,3,4 tetrahydroquinoline and 3,4-dihydro-3-methyl-2H-[1,4]benzoxazine using N-phthaloyl-(S)-amino acyl chlorides with alkyl side chains has been carried out. The influence of steric factors on the stereoselectivity of the acylation was demonstrated. The (S)-enantiomers of the heterocyclic amines (ee >99%) were obtained in good yields via a kinetic resolution protocol using N-phthaloyl-(S)-leucyl chloride

\\\\expert2\\NBO\\Tetrahedron Asymmetry\\2012, v. 23, p.1640.pdf
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15.
Инвентарный номер: нет.
   
   S 91


   
    Substituent effect on the stereoselectivity of acylation of racemic heterocyclic amines with N-phthaloyl-3-aryl-(S)-alanyl chlorides [Text] / G. L. Levit, D. A. Gruzdev, V. P. Krasnov, E. N. Chulakov, L. Sh. Sadretdinova, M. A. Ezhikova, M. I. Kodess, V. N. Charushin // Tetrahedron: Asymmetry . - 2011. - Vol. 22, № 2. - P185-189. - Bibliogr. : p. 189 (17ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The acylative kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and 2,3-dihydro-3-methyl-4H-1,4-benzoxazine using acyl chlorides of N-phthaloyl-(S)-phenylalanine, N-phthaloyl-3-(4-nitrophenyl)-(S)-alanine and N-phthaloyl-O-methyl-(S)-tyrosine as chiral resolving agents has been carried out. It is shown that the effectiveness of an acylative kinetic resolution depends on the electronic effects of substituents in the phenyl fragment of the acylating agent and increases as the electron-donating properties of the para-substituent (OMe H NO2) in phenyl fragment of N-phthaloyl-3-aryl-(S)-alanyl chlorides increase; conducting the process at a reduced temperature also contributes to an enhancement of the kinetic resolution

\\\\Expert2\\nbo\\Tetrahedron Asymmetry\\2011, v. 22, p.185.pdf
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16.
Инвентарный номер: нет.
   


   
    2-Arylpropionyl chlorides in kinetic resolution of racemic 3-methyl-2,3-dihydro-4H-[1,4]benzoxazines [Electronic resource] / E. N. Chulakov, D. A. Gruzdev, G. L. Levit, L. Sh. Sadretdinova, V. P. Krasnov, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2011. - Vol.60, №5. - С. 948-954. - Bibliogr. : p. 953-954 (34 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
KINETIC RESOLUTION -- ACYL CHLORIDES -- ENANTIOMERS
Аннотация: Kinetic resolution of racemic 3 methyl 2,3 dihydro 4H [1,4]benzoxazines in the reaction with chiral 2 arylpropionyl chloride predominantly yielded R*,R* diastereomers. Ibuprofen acyl chloride as acylating agent was found to be more selective and sensitive to the changes in the reaction temperature as compared to naproxen acyl chloride and 2 phenylpropionyl chloride

\\\\expert2\\NBO\\Russian Chemical Bulletin\\2011, 60 (5), 948-954.pdf
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17.
Инвентарный номер: нет.
   
   S 89


   
    Structure of diethyl (polyfluorobenzoyl)malonates and their thermal intramolecular cyclizat / D. N. Bazhin, E. V. Schegolkov, Yu. S. Kudyakova, Ya. V. Burgart, V. I. Saloutin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2011. - Vol.60, №5. - С. 929-932
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
POLYFLUOROBENZOYL -- POLYFLUOROBENZOYL CHLORIDES -- CYCLIZATION
Аннотация: The reaction of the C-ethoxymagnesium derivative of diethyl malonate with polyfluorobenzoyl chlorides affords the corresponding (polyfluorobenzoyl)malonates prone to thermal cyclization into coumarin derivatives. The compounds obtained are inherent in keto—enol tautomerism

\\\\Expert2\\nbo\\Russian Chemical Bulletin\\2011, 60 (5), 929-932.pdf
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18.
Инвентарный номер: нет.
   
   A 89


   
    Asymmetric induction in the reactions of azinones with C-nucleophiles [Electronic resource] / O. N. Chupakhin, I. N. Egorov, V. L. Rusinov, P. A. Slepukhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2010. - Vol. 59, № 5. - P991-1001
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
TRIAZINONES -- QUINOXALIN -- C-NUCLEOPHILES -- INDOLES
Аннотация: Effect of acylating agents on the course of addition of C-nucleophiles to 1,2,4- and 1,3,5-triazinones, as well as to quinoxalin-2(1H)-one, was studied. A series of new azinone derivatives was obtained. A method for the preparation of diastereomerically pure addition products of indoles to 1,2,4-triazinones and quinoxalin-2(1H)-one in the presence of N-Ts-L-amino acid acyl chlorides was suggested

\\\\Expert2\\nbo\\Russian Chemical Bulletin\\2010, 59 (5), 991-1001.pdf
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19.
Инвентарный номер: нет.
   
   A 19


   
    Acylative kinetic resolution of racemic amines using N-phthaloyl-(S)-amino acyl chlorides [Text] / D. A. Gruzdev, G. L. Levit, V. P. Krasnov, E. N. Chulakov, L. Sh. Sadretdinova, A. N. Grishakov, M. A. Ezhikova, M. I. Kodess, V. N. Charushin // Tetrahedron: Asymmetry . - 2010. - Vol. 21, № 8. - P936-942
ББК 54
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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20.
Инвентарный номер: нет.
   
   F 70


   
    Fluorine-containing heterocycles. XVIII. Monofluoro derivatives of quinazolines and 1,3-benzothiazin-4-ones [Electronic resource] / E. V. Nosova, A. A. Laeva, T. V. Trashakhova, A. V. Golovchenko, G. N. Lipunova, P. A. Slepukhin, V. N. Charushin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2009. - Vol. 45, № 6. - P904-912
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: 5- and 7-Fluoro-substituted quinazolines and 1,3-benzothiazin-4-ones were synthesized starting from 2-amino-6-fluorobenzonitrile and mono- and difluoro-substituted benzoic acid derivatives. The reactivities of di- and tetrafluoro-substituted benzoyl chlorides and benzoyl isothiocyanates in cyclocondensations leading to fluorinated quinazolines and 1,3-benzothiazines were compared

\\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2009, 45 (6), 904.pdf
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