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Svetlakov, N. V.; Nikitin, V. G.; Orekhova, A. O.

doi:10.1023/a:1019635811413

Cited by 10 publications

(7 citation statements)

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“…The solvent was removed in a vacuum at 70°C, the residue was dried by azeotropic distillation with benzene using Dean-Stark trap, then the product was fi ltered off and recrystallized from acetone-benzene mixture. Yield 7.4 g (92%), colorless crystals, R f 0.20 (F), mp 142-143°C (mp 140-144°C [12]). IR spectrum, ν, cm Oxidation of PEG 3400 .…”

Section: -Oxapentanedioic Acid (Vii)mentioning

confidence: 99%

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Design, synthesis, and properties of neoglycolipids based on ethylene glycoles conjugated with lactose as components of targeted delivery systems of biologically active compounds

2012

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Section: -Oxapentanedioic Acid (Vii)mentioning

confidence: 99%

“…In each event the adjustment of the individual reaction conditions allowed obtaining dicarboxylic acids VII-IX in 89-92% yields [12,13].…”

mentioning

confidence: 99%

Design, synthesis, and properties of neoglycolipids based on ethylene glycoles conjugated with lactose as components of targeted delivery systems of biologically active compounds

2012

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“…Thus the rate determining step proposed is: The small salt effect, increase in reaction rate on increasing the dielectric constant and straight line double reciprocal plots between 1/k versus 1/[TEG] with positive intercept at y-axis (Figure 3), support equation 12as being the rate determining step. The thus formed complex decomposes quickly into the products, equation (13).…”

Section: Mechanismmentioning

confidence: 99%

“…The main uses for TEG depend upon its hygroscopic properties. Oxidation of polyethylene glycols, different alcohols and diols by different oxidant has been carried out by various workers [2][3][4][5][6][7][8][9][10][11][12][13][14] but no one has ever used chloramine-T (p-Me-C 6 H 4 -SO 2 NClNa.5H 2 O) as an oxidant. Chloramine-T abbreviated as CAT, is a versatile oxidant [15][16][17][18][19] .In continuation of our work [20][21][22] C 16 TAB catalyzed oxidation of TEG by chloramine-T has been undertaken.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Effect of Cetyltrimethylammonium Bromide on the Oxidation of Triethylene glycol by Chloramine‐T in Acidic Medium

Sharma¹,

Sharma²,

Bhagwat³

2008

Journal of Chemistry

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The kinetics and mechanism of cetyltrimethylammonium bromide catalyzed oxidation of triethylene glycol [2,2'-ethylene diqxybis(ethanol)] by chloramine-T in acidic acid medium have been investigated. The reaction is first order dependence on chloramine-T and fractional order for triethylene glycol with excess concentration of other reactants. The catalytic effect due to cetyletrimethylammonium bromide has been studied. The small salt effect and increase in the reaction rate with increasing dielectric constant suggest the involvement of neutral molecule in the rate-determining step. The addition ofp-toluene sulfonamide retards the reaction rate. The effect of chloride ion on the reaction also studied. The effect of temperature on the reaction has been investigated in the temperature range 313-333K and thermodynamic parameters were calculated from the Arrhenious plot. A tentative mechanism consistent with the experimental results has been proposed.

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“…Such compounds include heterocyclic compounds such as isoquinoline derivatives. Diglycolic acid (3) was synthesized via oxidation of diethyleneglycol by HNO 3 according to the literature [8]. In continuation of systematic research on the synthesis of bis-tetrahydroisoquinolines via the Bischler-Napieralski reaction, we used diamides of glutaric (2) and diglycolic acids (3) in the reaction.…”

mentioning

confidence: 99%

Synthesis of bis-Tetrahydroisoquinolines Based on Homoveratrylamine and a Series of Dibasic Acids. 3.

et al. 2014

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Their structures were confirmed using IR and NMR spectra and an x-ray crystal structure analysis.Organic chemists are faced with the problem of creating effective synthetic pathways to previously unknown compounds with useful properties. Such compounds include heterocyclic compounds such as isoquinoline derivatives. Despite the variety of known structures, research on the development of methods for preparing isoquinoline alkaloids and their synthetic analogs is critical according to the number of publications [1][2][3].We showed earlier [4] that the cyclization of diamides obtained from homoveratrylamine (1) and a series of dibasic fatty acids (from C 6 to C 10 ) did not depend on the acid chain length whereas the cyclization of phthalic acid diamides depended on their structure [5]. In continuation of systematic research on the synthesis of bis-tetrahydroisoquinolines via the Bischler-Napieralski reaction, we used diamides of glutaric (2) and diglycolic acids (3) in the reaction.Methods for preparing diglycolic acid from chloroacetic acid gave poor results [6,7]. Diglycolic acid (3) was synthesized via oxidation of diethyleneglycol by HNO 3 according to the literature [8]. Use of 86% HNO 3 increased the yield of 3 to 90%.Diamides 4 and 5 were synthesized by heating previously formed salts of 2 and 3 with 1 whereas others [9] prepared diglycolic acid diamide in several steps. In the first step, the cyclic anhydride of diglycolic acid was prepared and used to acylate an amine to form the monoamide. Then, the diamide was obtained through the acid chloride of the second carboxylic acid. This decreased significantly the yield. The synthetic method proposed by us was performed in one flask in two steps with 86% (5) and 79% (4) yields.The structures of 4 and 5 were proved using IR and PMR spectra (see Experimental). IR spectra of 4 and 5 had strong absorption bands for amide carbonyl at 1638 and 1680 cm -1 , respectively.

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Cited by 10 publications

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Design, synthesis, and properties of neoglycolipids based on ethylene glycoles conjugated with lactose as components of targeted delivery systems of biologically active compounds

Design, synthesis, and properties of neoglycolipids based on ethylene glycoles conjugated with lactose as components of targeted delivery systems of biologically active compounds

Catalytic Effect of Cetyltrimethylammonium Bromide on the Oxidation of Triethylene glycol by Chloramine‐T in Acidic Medium

Synthesis of bis-Tetrahydroisoquinolines Based on Homoveratrylamine and a Series of Dibasic Acids. 3.

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