- Structure-retention relationship in a series of chiral 1,4-disubstituted piperazine derivatives on carbohydrate chiral stationary phases
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New racemic 1,4-disubstituted piperazines chemically named ethyl 2-[(4-pyrimidin-2yl-piperazine-1yl)carbonyl]C3-C5-alkanoates 1-7 were synthesized. The compounds were resolved into enantiomers on cellulose tris(4-methylbenzoate) and amylose tris(3,5-dimethylphenylcarbamate) stationary phases using hexane/propan-2-ol mobile phases. The optimum separation conditions for the compounds were obtained on cellulose tris(4-methylbenzoate) with 5% of 2-propanol in hexane. The relationship between structural and chromatographic parameters is discussed.
- Chilmonczyk, Zdzislaw,Sienicki, Lukasz,Lozowicka, Bozena,Lisowska-Kuzmicz, Malgorzata,Jonczyk, Anna,Aboul-Enein, Hassan Y.
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- Fe-Catalyzed reactions of 2-chloro-1,7-dienes and allylmalonates
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Fe(III)(BIAP)Cl3 complex catalyzes alkylative cyclization of 2-chloro-1,7-heptadiene in the presence of triethylaluminum. It also catalyzes deallylation of certain 2-allyl-2-substituted malonates under the same reaction conditions.
- Ne?as, David,Drabina, Pavel,Sedlák, Milo?,Kotora, Martin
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- Co-Catalytic Effects in Phase-Transfer Catalyzed Reactions
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The phase-transfer catalyzed alkylation reaction of diethyl malonate with butyl bromide using solid potassium carbonate as base could not be accelerated above a limiting reaction rate by increasing the concentration of the onium salt catalyst.The rate limit could be exceeded by using crown ether in addition to an onium salt.Polyethylene glycols exhibit a similar effect.These results were used to improve the yields in a series of related alkylation reactions.
- Szabo, G. T.,Aranyosi, K.,Csiba, M.,Toke, L.
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- Alkylation of malonic and acetoacetic esters in an ionic liquid
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1-Butyl-3-methylimidazolium hexafluorophosphate ([bmim][PF6]) has been used as a recyclable medium in the alkylation of malonic and acetoacetic esters with alkyl, benzyl and prenyl halides.
- Kryshtal, Galina V.,Zhdankina, Galina M.,Zlotin, Sergei G.
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- Catalytic deallylation of allyl- and diallylmalonates
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Substituted allylmalonates undergo the selective C-C bond cleavage in the presence of triethylaluminum and a catalytic amount of nickel and ruthenium phosphine complexes, resulting in the loss of the allyl moiety and formation of monosubstituted malonates. Comparison of reactivity of the nickel and ruthenium complexes showed that the use of the former is general with respect to the structure of the substituted allylmalonates, and the activity of the latter depended on the substitution pattern of the double bond of the allylic moiety. The smooth deallylation may encourage the use of the allyl group as a protective group for the acidic hydrogen in malonates. Copyright
- Necas, David,Tursky, Matyas,Kotora, Martin
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- Xanthenylacetic Acid Derivatives Effectively Target Lysophosphatidic Acid Receptor 6 to Inhibit Hepatocellular Carcinoma Cell Growth
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Despite the increasing incidence of hepatocellular carcinoma (HCC) worldwide, current pharmacological treatments are still unsatisfactory. We have previously shown that lysophosphatidic acid receptor 6 (LPAR6) supports HCC growth and that 9-xanthenylacetic acid (XAA) acts as an LPAR6 antagonist inhibiting HCC growth without toxicity. Here, we synthesized four novel XAA derivatives, (±)-2-(9H-xanthen-9-yl)propanoic acid (compound 4 – MC9), (±)-2-(9H-xanthen-9-yl)butanoic acid (compound 5 – MC6), (±)-2-(9H-xanthen-9-yl)hexanoic acid (compound 7 – MC11), and (±)-2-(9H-xanthen-9-yl)octanoic acid (compound 8 – MC12, sodium salt) by introducing alkyl groups of increasing length at the acetic α-carbon atom. Two of these compounds were characterized by X-ray powder diffraction and quantum mechanical calculations, while molecular docking simulations suggested their enantioselectivity for LPAR6. Biological data showed anti-HCC activity for all XAA derivatives, with the maximum effect observed for MC11. Our findings support the view that increasing the length of the alkyl group improves the inhibitory action of XAA and that enantioselectivity can be exploited for designing novel and more effective XAA-based LPAR6 antagonists.
- Gnocchi, Davide,Cavalluzzi, Maria M.,Mangiatordi, Giuseppe F.,Rizzi, Rosanna,Tortorella, Cosimo,Spennacchio, Mauro,Lentini, Giovanni,Altomare, Angela,Sabbà, Carlo,Mazzocca, Antonio
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- Solid-liquid phase transfer catalytic synthesis. XII: Microwave irradiated alkylation of diethyl malonate
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The anion derived from diethyl malonate reacts with a series of halides readily under microwave irradiation, and the isolated yield of alkylated products varying from 64% to 86%.
- Wang,Deng,Mi,Jiang
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- Preparation of mono-substituted malonic acid half oxyesters (SMAHOs)
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The use of mono-substituted malonic acid half oxyesters (SMAHOs) has been hampered by the sporadic references describing their preparation. An evaluation of different approaches has been achieved, allowing to define the best strategies to introduce diversity on both the malonic position and the ester function. A classical alkylation step of a malonate by an alkyl halide followed by a monosaponification gave access to reagents bearing different substituents at the malonic position, including functionalized derivatives. On the other hand, the development of a monoesterification step of a substituted malonic acid derivative proved to be the best entry for diversity at the ester function, rather than the use of an intermediate Meldrum acid. Both these transformations are characterized by their simplicity and efficiency, allowing a straightforward access to SMAHOs from cheap starting materials.
- Condon, Sylvie,Le Gall, Erwan,Pichon, Christophe,Presset, Marc,Xavier, Tania
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supporting information
p. 2085 - 2094
(2021/09/02)
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- Synthesis of Cyclopentenones through Rhodium-Catalyzed C-H Annulation of Acrylic Acids with Formaldehyde and Malonates
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An efficient rhodium-catalyzed protocol for the synthesis of cyclopentenones based on a three-component reaction of acrylic acids, formaldehyde, and malonates via vinylic C-H activation is reported. Exploratory studies showed that 5-alkylation of as-prepared cyclopentenones could be realized smoothly by the treatment of a variety of alkyl halides with a Na2CO3/MeOH solution. Excess formaldehyde and malonate led to a multicomponent reaction that afforded the multisubstituted cyclopentenones through a Michael addition.
- Yu, Shuling,Hong, Chao,Liu, Zhanxiang,Zhang, Yuhong
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supporting information
p. 5054 - 5059
(2021/07/20)
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- Synthesis of protected α-amino acids: Via decarboxylation amination from malonate derivatives
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A general and efficient strategy for the synthesis of protected α-amino acids is reported. The method uses malonate derivatives as the starting materials and Cs2CO3 as a base at 60 degrees, giving α-amino acid derivatives in moderate yields by releasing CO2. This methodology shows broad substrate scope (primary and secondary acids), excellent functional group tolerance and high efficiency to give the desired products under mild reaction conditions. It also allows the construction of β and γ-amino acids and other unnatural products.
- Dai, Qipu,Fu, Hui,Hu, Changwen,Li, Peihe,Li, Xiaoying,Wang, Zheng
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p. 4439 - 4446
(2020/10/20)
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- Synthesis method of phenylbutazone drug intermediate diethyl n-butylmalonate
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The invention relates to a synthesis method of a phenylbutazone drug intermediate diethyl n-butylmalonate, which comprises the following steps: adding 3L of dichloroethylamine into a reaction vessel which is provided with a stirrer, a thermometer, a reflux condenser and a dropping funnel, adding 6.2 mol of cuprous chloride in batches, controlling the stirring rate at 130-150 rpm, heating the solution to 70-75 DEG C, reacting for 3-4 hours, and dropwisely adding 6.1 mol of diethyl malonate; and after finishing addition, continuing stirring for 70-90 minutes, adding 6.6-6.8 mol of n-aminobutane, reacting for 5-6 hours, refluxing for 3-4 hours, distilling under reduced pressure to remove dichloroethylamine, cooling the solution to 15-18 DEG C, adding 3L of sodium chloride solution, continuing for 40-70 minutes while keeping the stirring rate at 160-190 rpm, separating out the water layer, distilling the oil layer under reduced pressure, collecting the 130-135-DEG C fraction, washing with salt solution, washing with hexane, and recrystallizing in ethyl acetate to obtain the diethyl n-butylmalonate, wherein the mass percent of the sodium chloride solution is 15-20%, and the pressure of the reduced pressure distillation is 2.2-2.3 KPa.
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Paragraph 0007; 0015; 0016
(2017/03/08)
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- Nano-K2CO3: Preparation, characterization and evaluation of reactive activities
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A novel base, nano-K2CO3, was easily prepared by ultrafine wet milling. The surface properties and the reactive activities of nano-K2CO3 were characterized. It was found that such a base showed higher basicity than normal K2CO3 and could replace sodium (or potassium) alkoxide to carry out monoalkylation and oximation of active methylene compounds. The nano-K2CO3 could be regenarated and reused 10 times without loss of its reactive activity.
- Li, Jun-Zhang,Fan, Shi-Ming,Sun, Xuan-Fei,Liu, Shouxin
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p. 1865 - 1869
(2016/01/20)
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- The potential of methylsiloxanes as solvents for synthetic chemistry applications
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The potential use of volatile methylsiloxanes (VMSs) as solvents for chemicals synthesis has been explored. Assessment of the environmental impact of these VMS solvents is made and found to be significantly lower than those of the non-polar organic solvents that they have the potential to replace. The polarities of the VMSs, as expressed by empirical polarity measurements, and miscibilities with other liquids are found to be similar to those of alkane solvents. Finally, some uses of VMSs as solvents for both organic and inorganic transformations are described. The VMSs provide environmentally more sustainable (greener) alternatives to the nonpolar solvents that they have the potential to replace.
- Ab Rani, Mohd Azri,Borduas, Nadine,Colquhoun, Victoria,Hanley, Robert,Johnson, Henry,Larger, Solene,Lickiss, Paul D.,Llopis-Mestre, Veronica,Luu, Selina,Mogstad, Martin,Oczipka, Philipp,Sherwood, James R.,Welton, Tom,Xing, Jun-Yi
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p. 1282 - 1296
(2014/03/21)
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- Synthesis, antibacterial activity, and biological evaluation of formyl hydroxyamino derivatives as novel potent peptide deformylase inhibitors against drug-resistant bacteria
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Peptide deformylase (PDF) has been identified as a promising target for novel antibacterial agents. In this study, a series of novel formyl hydroxyamino derivatives were designed and synthesized as PDF inhibitors and their antibacterial activities were evaluated. Among the potent PDF inhibitors (1o, 1q, 1o′, 1q′, and 1x), in vivo studies showed that compound 1q possesses mild toxicity, a good pharmacokinetic profile and protective effects. The good in vivo efficacy and low toxicity suggest that this class of compounds has potential for development and use in future antibacterial drugs.
- Yang, Shouning,Shi, Wei,Xing, Dong,Zhao, Zheng,Lv, Fengping,Yang, Liping,Yang, Yushe,Hu, Wenhao
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p. 133 - 152
(2014/10/15)
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- Synthesis, characterization, and electrochemical study of diiron organometallic derivatives of 2,6-dibutyl-4,8-dimethyl-1,5-dihydro-S-indacene
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A new fused ring compound, 2,6-dibutyl-4,8-dimethyl-1,5-dihydro-s-indacene (VII) (H2L), has been synthesized from 2,5-dimethyl-1,4- dibromomethylbenzene in almost quantitative yield. Two organomtallic binuclear complexes, [CpFe-L-FeCp] (1) and the mixed-valence compound [CpFe-L-FeCp] + BF-4 (2), have been characterized by spectroscopic and electrochemical techniques. The cyclic voltammogram of 1 exhibits a potential difference of 668 mV between two redox peaks and the UV-vis-NIR spectra of compound 2 shows an intervalance charge transfer band at 1794 nm. The information gathered by these techniques indicates that the studied binuclear complex has strong interaction between the two metal centres.
- Amshumali,Arancibia, Veronica,Manriquez, Juan M.,Chavez, Ivonne
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p. 727 - 731
(2013/08/23)
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- Preparation and ESR characterization of polyalkyl-s-indacenyl anion-radicals from polyalkyl-1,5-dilithio-s-indacenes
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Polyalkyl-(or chloropolyalkyl)-s-indacenyl anion radicals were obtained from the organodilithium derivatives of the corresponding substituted-1,5- dihydro-s-indacenes by three different methods: (i) UV photolysis, (ii) oxidation by a ferrocenium salt, (iii) single electron transfer reaction from an electron rich olefin. The last reaction (iii) involves transient formation of an unstable polyalkyl-lithio-s-indacenyl imidazolidinium salt. The same salt, obtained by another way by reacting 1,3-dimethylimidazolidinium chloride with the polyalkyl-1,5-dilithio-s-indacene, also leads to the corresponding lithium polyalkyl-s-indacenyl anion radical. All lithium polyalkyl-s-indacenyl anion radicals studied were characterized from their ESR spectra. They present a characteristic symmetrical spin distribution. On the contrary a Rhodium-COD polyalkyl-s-indacene radical presents a non symmetrical spin distribution.
- Adams,Araneda,Morales,Chavez,Manriquez,Mac-Leod Carey,Katir,Castel,Rivière,Rivière-Baudet,Dahrouch,Gatica
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experimental part
p. 44 - 52
(2011/03/23)
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- Synthesis of 3-alkyl(aryl)thietanes
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A preparative procedure for the synthesis of thietanes bearing alkyl substituents in the β-position was developed. Using this procedure, 3-substituted thietanes can be obtained in four steps with an ultimate yield of > 50%. 3-R-thietanes (where R = CH3, C4H9, C5H11, C6H13, C6H 5) and the corresponding sulfoxides and sulfones were synthesized and examined. The feasibility of preparation of gem-3,3-substituted thietanes was exemplified by the synthesis of 3,3-dihexylthietane.
- Shevchenko,Volynskii
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body text
p. 123 - 128
(2010/02/28)
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- Peptide deformylase inhibitors of Mycobacterium tuberculosis: Synthesis, structural investigations, and biological results
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Bacterial peptide deformylase (PDF) belongs to a subfamily of metalloproteases catalyzing the removal of the N-terminal formyl group from newly synthesized proteins. We report the synthesis and biological activity of highly potent inhibitors of Mycobacterium tuberculosis (Mtb) PDF enzyme as well as the first X-ray crystal structure of Mtb PDF. Structure-activity relationship and crystallographic data clarified the structural requirements for high enzyme potency and cell based potency. Activities against single and multi-drug-resistant Mtb strains are also reported.
- Pichota, Arkadius,Duraiswamy, Jeyaraj,Yin, Zheng,Keller, Thomas H.,Alam, Jenefer,Liung, Sarah,Lee, Gladys,Ding, Mei,Wang, Gang,Chan, Wai Ling,Schreiber, Mark,Ma, Ida,Beer, David,Ngew, Xinyi,Mukherjee, Kakoli,Nanjundappa, Mahesh,Teo, Jeanette W.P.,Thayalan, Pamela,Yap, Amelia,Dick, Thomas,Meng, Wuyi,Xu, Mei,Koehn, James,Pan, Shi-Hao,Clark, Kirk,Xie, Xiaoling,Shoen, Carolyn,Cynamon, Michael
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scheme or table
p. 6568 - 6572
(2009/09/30)
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- COMPOSITION FOR ELECTROLYTIC SOLUTION AND PROCESS FOR PRODUCING THE SAME
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An electrolytic solution for operating electrolytic capacitors which deteriorates extremely little in electrical properties even when used in a high-tension capacitor. The electrolytic solution comprises a compound expressed by general formula (1) below a
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- Preparation of phosphinodipeptide analogs as building blocks for pseudopeptides synthesis
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A simple and effective preparation of phosphinodipeptides, in good overall yields, has been developed. This one pot procedure, allowing the variation of the substituents in α and/or β position to the phosphorus atom and also in α position to the nitrogen atom, consists in the addition of alkyl hypophosphites to imines, followed by Michael-addition on acrylates. To show the value of phosphinodipeptides analogs 1 as synthetic intermediates, selective deprotections of the three functional groups are described.
- Cristau, Henri-Jean,Coulombeau, Agnès,Genevois-Borella, Arielle,Sanchez, Frédéric,Pirat, Jean-Luc
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p. 381 - 391
(2007/10/03)
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- Process for the C-alkylation of malonic esters using phase-transfer agents
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The invention relates to a process for the C-alkylation of dialkyl malonates, in which a dialkyl malonate is reacted with an alkyl halide in the presence of potassium carbonate as a hydrogen halide acceptor in an inert solvent, and a phase-transfer cataly
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- SYNTHESIS OF NEW LIPOPHILIC LIGANDS AND NMR MEASUREMENT OF THEIR CRITICAL MICELLAR CONCENTRATION (CMC)
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New lipophilic ligands are synthesized to build potential Magnetic Resonance Imaging contrast agents (MRI).Using the evolution of 1H-NMR chemical shifts δ with concentration of monomer in D2O, the critical micellar concentration (CMC) has been measured. - Key words: Contrast agents; M.R.I.; C.M.C.; micelles.
- Nguyen, M. V. D.,Brik, M. E.,Ouvrard, B. N.,Courtieu, J.,Nicolas, L.,Gaudemer, A.
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p. 181 - 184
(2007/10/03)
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- Carbon-Carbon Bond Formation with New Mitsunobu Reagents
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The efficiency of three azodicarboxylic acid derivatives and a stabilized phosphorane in the Mitsunobu type C-C bond formation was compared utilizing the reactions of three nucleophiles of different pKa's and several alcohols of different structure types.The study established the characteristics of each reagent.The synthesis of two insect pheromone analogs was accomplished effectively using these homologation reactions.
- Tsunoda, Tetsuto,Nagaku, Miwa,Nagino, Chisato,Kawamura, Yumi,Ozaki, Fumie,et al.
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p. 2531 - 2534
(2007/10/02)
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- Synthesis of Dinitroxides of Potential Use as Contrast Agent in MRI
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Dinitroxides derived from 6-alkyl-1,4,8,11-tetraazaundecane-5,7-dione have been synthesized in three steps.These compounds, which contain two paramagnetic centers, are more effective proton relaxation agents than those containing only one nitroxyl moiety and could be used in smaller quantities as contrast agents in MRI.
- Brik, Mohab-Eddine,Nguyen, Marguerite Van Duong,Nicolas, Louisette,Courtieu, Jacques,Gaudemer, Alain
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p. 2183 - 2190
(2007/10/02)
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- 1,1′-(azodicarbonyl)dipiperidine-tributylphosphine, a new reagent system for mitsunobu reaction
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The 1,1′-(azodicarbonyl)dipiperidine (ADDP)-tributylphosphine (TBP) system was developed as a new institute of the Mitsunobu reagent. The new system activates nitrogen or carbon nucleophiles, known to be innert or poorly reactive with the Mitsunobu reagent, to react with alcohols satisfactorily forming C-N or C-C bonds. The inversion of stereogenic carbinyl carbons was confirmed in the acylaltion reaction of two sec-alcohols.
- Tsunoda, Tetsuto,Yamamiya, Yoshiko,Ito, Sho
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p. 1639 - 1642
(2007/10/02)
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- Synthesis of a new chiral phase-transfer catalyst: Chemical activity in alkylation reactions
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A new chiral phase-transfer catalyst (3S,4S)-1-benzyl-1-methyl-3,4- pyrrolidin-diol-onium iodide (2) synthesized, is found to be more active than the conventional tetraaklylammonium salts in alkylation reactions on active methylene compounds under usual solid-liquid phase-transfer conditions.
- Valli,Sarma,Choudary
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p. 481 - 482
(2007/10/02)
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- Molecular Recognition and Catalysis: Acceleration of Acyl Transfer Reactions by a Hydrogen-Bonding Receptor
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A hydrogen-bonding receptor containing an appended thiol has been synthesized and shown to cause large rate accelerations (kobs/kuncat>104) in the thiolysis reaction of complementary barbiturate acetate derivatives.
- Tecilla, Paolo,Hamilton, Andrew D.
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p. 1232 - 1234
(2007/10/02)
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- Synthesis and Liquid Crystal Properties of Dimethylene Linked Compounds Incorporating the Cyclobutane or Spiroheptane Rings
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The preparation of sixteen dimethylene linked compounds is described heptane ring>, and a comparison is made between the transition temperatures of these compounds and those of the corresponding esters.This comparison once again highlights the fact that the cyclobutane ring should be regarded, in terms of its ability to promote nematic thermal stability, as a "chain stiffener rather than as a ring system.A comparison is also made of the nematic thermal stabilities of the trans-cyclobutane and the spiroheptane systems and of the trans-cyclohexane and the spiroundecane systems.
- Chan, L. K. M.,Gemmell, P. A.,Gray, G. W.,Lacey, D.,Toyne, K. J.
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p. 229 - 246
(2007/10/02)
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- Substituent effects on partition coefficients of barbituric acids
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Precise partition coefficients in 1-octanol-water at 25°C were determined for three 2-thiobarbituric acids and 14 barbituric acids with a wider range of substituents. The experimental log P values (log P(exp)) of barbituric acids were correlated with the carbon number and the branching effect of the C5 substituent(s) by linear regression analysis. The carbon number term makes a major contribution to the partition coefficients. The contribution of the polar effect of the C5 substituents was insignificant in contrast to a previous report. Hydrophobic constants (π) were determined for allyl, phenyl, and chloro-substituents, and these emperical π values gave much closer predicted calculated log P (log P(calc)) values when applied to the reported log P(exp) values.
- Wong,McKeown
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p. 926 - 932
(2007/10/02)
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- Alkylation Reactions of Ethyl Malonate, Ethyl Acetoacetate, and Acetylacetone by Gas-Liquid Phase-Transfer Catalysis (G.L.-P.T.C)
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Malonyl, acetoacetyl, and acetylacetonyl alkylation reactions have been carried out in the gaseous state under gas-liquid phase-transfer catalysis (g.l-p.t.c) conditions using potassium carbonate or sodium hydrogencarbonate as the base.No alkali metal was used to generate the reactive anion.No solvents are used in the process, and the reaction mixture requires no stirring.The phase-transfer catalysts which promote the reaction: phosphonium salts, crown ethers, and poly(ethylene glycol) are also the medium in which the reaction occurs; they direct C- or O- alkylation, as a function of the methylene compound and the alkylating agent used.The malonic ester alkylation using poly(ethylene glycol) gives rise to improved selectivity for C-monoalkylation compared with the other catalysts.
- Tundo, Pietro,Venturello, Paolo,Angeletti, Enrico
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p. 2159 - 2162
(2007/10/02)
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- LIQUID CRYSTAL MATERIALS WITH SULFUR ATOMS INCORPORATED IN THE PRINCIPAL STRUCTURE: 1. NEW LIQUID CRYSTAL COMPOUNDS WITH 1,3-DITHIANE RING.
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2-(p-Substituted phenyl)-5-alkyl-1,3-dithianes, new liquid crystals, were synthesized by the thioacetalization of the corresponding aldehydes and dithiols. These compounds have characteristic supercooling states, exhibit monotropic liquid crystal phases even in the case of long terminal alkyl substituents. The mesomorphic characteristics of these compounds were different from those of the corresponding 1,3-dioxanes, this must originate in the difference in the molecular width caused by the difference in the atomic volume between sulfur and oxygen.
- Haramoto,Nobe,Kamogawa
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p. 1966 - 1969
(2007/10/02)
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- Mesomorphic Phenyl Benzoate and 1,3-Dioxane Derivatives Bearing Terminal Vinyl Group
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4-Alkylphenyl 2-chloro-4-(4-vinylbenzoyloxy) benzoates and 2-phenyl-1,3-dioxane derivatives with terminal vinyl groups were synthesized.Most of the novel compounds obtained possess characteristic mesomorphic ranges.
- Kamogawa, Hiroyoshi,Hirose, Tomoki,Nanasawa, Masato
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p. 3517 - 3518
(2007/10/02)
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- Lipophilic Complexones, Part 3. Synthesis of Polyamines Derived from 2-Alkyl-1,3-propanediols and 2,2-Bis(hydroxymethyl)alkanols
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Lipophilic di-, tri-, tetra-, and hexaamines were synthesized from 2-alkyl-1,3-propanediols and 2,2-bis(hydroxymethyl)alkanols.The alcohols were converted into the sulfonate esters which were substituted with ethylenediamine or sodium azide.The azides were directly reduced to give amines.Also dioxyethylenated 2-octadecyl-1,3-propanediol yielded the corresponding amine.Some amines were converted into the salicylidene derivatives. - Keywords: Complexone; Polyamines
- Skarzewski, Jacek,Daniluk, Ewa
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p. 1071 - 1078
(2007/10/02)
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