- Synthesis of fluorinated pyrimidinones
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A method for the construction of fluorinated pyrimidinones based on the reaction of cyanodifluoromethyl- substituted amines with isocyanates is described. The use of ortho-iodophenylisocyanate in this reaction followed by copper catalyzed intramolecular amination affords fluorinated fused heterocycles - 4-fluoropyrimido[1,6-a]benzimidazol-1(2H)-ones.
- Kosobokov, Mikhail D.,Struchkova, Marina I.,Arkhipov, Dmitry E.,Korlyukov, Alexander A.,Dilman, Alexander D.
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- Gold(I) biscarbene complexes derived from vascular-disrupting combretastatin A-4 address different targets and show antimetastatic potential
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Gold N-heterocyclic carbene (NHC) complexes are an emerging class of anticancer drugs. We present a series of gold(I) biscarbene complexes with NHC ligands derived from the plant metabolite combretastatin A-4 (CA-4) that retain its vascular-disrupting eff
- Muenzner, Julienne K.,Biersack, Bernhard,Kalie, Hussein,Andronache, Ion C.,Kaps, Leonard,Schuppan, Detlef,Sasse, Florenz,Schobert, Rainer
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supporting information
p. 1195 - 1204
(2014/06/09)
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- Synthesis of 2-alkyl-1-aryl-1,2-dihydrochromeno[2,3-c]pyrrole-3,9-dione derivatives
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A preparative procedure for the synthesis of 2-alkyl-1-aryl-1,2- dihydrochromeno[2,3-c]pyrrole-3,9-diones from methyl 4-(o-hydroxyphenyl)-2,4- dioxobutanoate, aromatic aldehyde, and aliphatic amine is described.
- Vydzhak,Panchishin, S. Ya.
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experimental part
p. 2391 - 2397
(2009/05/30)
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- SYNTHESIS OF SUBSTITUTED 5-CHLOROMETHYL-1,3-OXAZOLIDINES
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Substituted 5-chloromethyl-1,3-oxazolidines were synthesized from 1-chloro-2,3-epoxypropane and Schiff bases in carbon tetrachloride in the presence of stannic chloride at 5-10 deg C.It was shown by 1H NMR spectroscopy that 2,3-diaryl-5-chloromethyl-1,3-oxazolidines are formed as a single diastereomer while N-alkyl-substituted 5-chloromethyl-1,3-oxazolidines are formed as mixtures of two stereoisomers.
- Bulatova, O. F.,Romanov, N. A.,Chalova, O. B.,Rakhmankulov, D. L.
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- Reactions of N-Chloro-N-alkylbenzylamines with Amines in Acetonitrile. Origin of Steric Effect in Imine-Forming Elimination
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Reaction of N-chloro-N-alkylbenzylamines in which the alkyl group is Me, Et, i-Pr, sec-Bu, and t-Bu with MeNH2 and Et2NH in MeCN have been studied kinetically.The eliminations are quantitative and regiospecific, producing only N-benzylidenealkylamines.The relative rates of elimination for Me/Et/i-Pr/sec-Bu/t-Bu alkyl substituents are 1/0.6/0.4/0.3/0.1 with MeNH2 and 1/0.5/0.3/0.2/0.03 with Et2NH, respectively.Comparison with published data reveals that Charton's value for the imine-forming elimination decreases with the variation of the base-solvent from MeONa-MeOH to MeNH2-MeCN but increases when the base is changed from MeNH2 to Et2NH.For a given base, Hammett ρ and kH/kD values decrease and the ΔH(excit.) and ΔS(excit.) values increase with bulkier alkyl substituents.From these results, the origin of the steric effect in imine-forming elimination is attributed to the repulsive interaction between the alkyl group and the base in the transition state.
- Cho, Bong Rae,Suh, Young Wook
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p. 2855 - 2858
(2007/10/02)
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- Reactions of N-Chlorobenzylalkylamines with Sodium Methoxide in Methanol. Steric Effects in Elimination Reactions
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Reactions of N-chlorobenzylalkylamines in which the alkyl group is Me, Et, i-Pr, t-Bu, and sec-Bu with MeONa-MeOH have been investigated kinetically.The eliminations are quantitative and regiospecific, producing only benzylidenealkylamines.The reactions are first order in base and first order in substrate, and an E2 mechanism is evident.The relative rates of elimination at 25 deg C are 1/0.5/0.3/0.2/0.01 for Me/Et/i-Pr/sec-Bu/t-Bu alkyl substituents, respectively.The results are attributed to repulsive interaction between the alkyl group and the base in the transition state.Hammett ρ and kH/kD values decreased, but the ΔH(excit.) and ΔS(excit.) values increased with bulkier alkyl substituents.Changes in the transition-state parameters with the substrate steric effect are interpreted with variation in structure of the imine-forming transition states.
- Cho, Bong Rae,Maeng, Jun Ho,Yoon, Jong Chan,Kim, Tae Rin
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p. 4752 - 4756
(2007/10/02)
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- Benzylamines: Synthesis and evaluation of antimycobacterial properties
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The synthesis of benzylamines with various N-alkyl chains and substituents in the aromatic system as well as their evaluation on Mycobacterium tuberculosis H 37 Ra are described. The most active compounds in this test, N-methyl-3-chlorobenzylamine (MIC 10.2 μg/mL), N-methyl-3,5-dichlorobenzylamine (93, MIC 10.2 μg/mL), and N-butyl-3,5-difluorobenzylamine (MIC 6.4 μg/mL), also exhibited a marked inhibitory effect on Mycobacterium marinum and Mycobacterium lufu used for the determination of antileprotic properties. The combination of 93 with aminosalicylic acid, streptomycin, or dapsone exert marked supra-additive effects on M. tuberculosis H 37 Ra.
- Meindl,Von Angerer,Schonenberger,Ruckdeschel
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p. 1111 - 1118
(2007/10/02)
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- N,N'-Dialkyl-1,2-bis(hydroxyphenyl)ethylenediamines and N,N'-Dialkyl-4,5-bis(4-hydroxyphenyl)imidazolidines: Syntheses and Evaluation of Their Mammary Tumor Inhibiting Activity
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Diastereomeric N,N'-dialyl-1,2-bis(hydroxyphenyl)ethylenediamines (5) were synthesized and tested for their affinity for the estradiol receptor.Only the (+/-)-1,2-bis(4-hydroxyphenyl)ethylenediamines with the alkyl groups C3H7 a=1.1
- Angerer, Erwin von,Egginger, Guenter,Kranzfelder, Gerhard,Bernhauer, Horst,Schoenenberger, Helmut
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p. 832 - 837
(2007/10/02)
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