- Synthesis and characterization of polyamidoamine dendrimers surface-functionalized with bromotricarbonylpyridyliminerhenium(I) units
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A novel type of rhenium-containing dendrimers has been prepared and characterized. A series of Schiff base-terminated PAMAM dendrimers were prepared by condensing the terminal amine groups of PAMAM dendrimers with pyridine-2-carboxaldehyde. Complete condensation of the terminal amines was confirmed by 1H NMR spectroscopy. Bromotricarbonylrhenium(I) moieties were introduced onto the surface of these modified PAMAM derivatives by refluxing with bromopentacarbonylrhenium(I). These complexes had been characterized by a variety of analytical and spectroscopic techniques and their IR, NMR, and mass spectra discussed. The crystal structure of the model compound [(CH3CONHCH2CH2N{double bond, long}CH{single bond}Py)ReBr(CO)3] confirms a facial configuration of the three carbonyl ligands. UV-Vis absorption spectroscopy suggests that the {Re(CO)3} moieties are quite far apart even in the second generation PAMAM dendrimers and do not interact with one another. In fact, the intensity of the metal-to-ligand (dπ-pπ*) charge-transfer is a linear function of the number of {Re(CO)3} chromophores.
- Zhao, Xinxin,Yan, Yaw-Kai,Chu, Chit-Kay
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- Rechargeable hydrogen storage system based on the dehydrogenative coupling of ethylenediamine with ethanol
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A novel and simple hydrogen storage system was developed, based on the dehydrogenative coupling of inexpensive ethylenediamine with ethanol to form diacetylethylenediamine. The system is rechargeable and utilizes the same ruthenium pincer catalyst for both hydrogen loading and unloading procedures. It is efficient and uses a low catalyst loading. Repetitive reversal reactions without addition of new catalyst result in excellent conversions in both the dehydrogenation and hydrogenation procedures in three cycles. In support of the hydrogen economy: An efficient and simple homogeneous hydrogen carrier system was developed based on the dehydrogenative coupling of ethylenediamine with ethanol to form diacetylethylenediamine. The same ruthenium pincer catalyst is used for both hydrogen loading and unloading reactions.
- Hu, Peng,Ben-David, Yehoshoa,Milstein, David
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- Structural analysis of ATP analogues compatible with kinase-catalyzed labeling
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Kinase-catalyzed protein phosphorylation is an important biochemical process involved in cellular functions. We recently discovered that kinases promiscuously accept γ-modified ATP analogues as cosubstrates and used several ATP analogues as tools for stud
- Suwal, Sujit,Senevirathne, Chamara,Garre, Satish,Pflum, Mary Kay H.
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- Unusual formation of imidazooxazolone in the reaction of 1-[(2-acetylamino)ethyl]imidazolone with KSCN in the presence of AcOH
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1-[(2-Acetylamino)ethyl]imidazolone was introduced for the first time in the condensation with KSCN in the presence of AcOH and imidazooxazolone was unexpectedly obtained. This result was possible only because of the unique character of 1-((2-acetylamino)ethyl)imidazolone, which has an intramolecular N-H O-H hydrogen bond and, therefore, reacts with the NCS anion to give only imidazooxazolone.
- Baranov, Vladimir V.,Antonova, Maria M.,Karnoukhova, Valentina A.,Kravchenko, Angelina N.
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- The mechanisms of the formation of by-products in the catalytic synthesis of C-alkylimidazoles from diamines and carboxylic acids
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The formation of 1-ethyl-2-methylimidazole (1-Et-2-MI) and 1-ethyl-2-methylimidazoline (1-Et-2-MIN), intermediates in the synthesis of 2-methylimidazole (2-MI) from ethylenediamine (EDA) and AcOH in the presence of a platinum-on-alumina catalyst, was studied.Using CH3(14)COOH the incorporation of two acetate units into 1-Et-2-MI and 1-Et-2-MIN molecules was demonstrated.The same products were also obtained on dehydrogenation of 2-methylimidazoline (2-MIN) under mild conditions (220-230 deg C).A part of the latter is transformed to N-ethyl ethylendiamine (EEDA) and EDA.These facts indicate that both 1-Et-2-MI and 1-Et-2-MIN result from hydrogenolysis of the imidazoline ring with subsequent ethylation.A reverse reaction, the C5-cyclization of EEDA, was also observed.The formation of 2-MI is favored by increasing temperature.
- Gitis, K. M.,Raevskaya, N. I.,Isagulyants, G. V.
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- THE STAGED SYNTHESIS OF 2-METHYLIMIDAZOLE FROM ETHYLENEDIAMINE AND ACETIC ACID IN THE PRESENCE OF A BIFUNCTIONAL ALUMINOPLATINUM CATALYST
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An investigation has been conducted into the staged synthesis of 2-methylimidazole from ethylenediamine and acetic acid in the presence of a bifunctional aluminoplatinum catalyst.It has been shown that the formation stage of 2-methylimidazoline occurs more quickly on γ-Al2O3 than its dehydrogenation on the Pt centers.From a comparison of the processes of dehydrogenation of 2-methylimidazoline in the molten phase and in aqueous solution it follows that the water eliminated in the imidazoline formation stage could cause the decrease in activity during the dehydrogenation on the Pt centers.The structures of the secondary and intermediate products have been established for each stage of the process and their formation routes are discussed. Keywords: aluminoplatinum catalysts, bifunctional catalysis, alkylimidazoles, 2-methylimidazole.
- Gitis, K. M.,Raevskaya, N. I.,Isagulyants, G. V.
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- WDR5 INHIBITORS AND MODULATORS
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Isoquinolmone compounds and derivatives inhibit WDR5 and associated protein-protein interactions, and the compounds and their pharmaceutical compositions are useful for treating disorders and conditions in a subject, such as cancer cell proliferation.
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Paragraph 00326; 00327
(2021/05/15)
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- Unusual formation of imidazooxazolone in the reaction of 1-[(2-Acetylamino)ethyl]imidazolone with KSCN in the presence of AcOH
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1-[(2-Acetylamino)ethyl]imidazolone was introduced for the first time in the condensation with KSCN in the presence of AcOH and imidazooxazolone was unexpectedly obtained. This result was possible only because of the unique character of 1-((2-Acetylamino)ethyl)imidazolone, which has an intramolecular N-H...O-H hydrogen bond and, therefore, reacts with the NCS anion to give only imidazooxazolone.
- Baranov, Vladimir V.,Antonova, Maria M.,Karnoukhova, Valentina A.,Kravchenko, Angelina N.
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- Simple and Versatile Laboratory Scale CSTR for Multiphasic Continuous-Flow Chemistry and Long Residence Times
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A universal multistage cascade CSTR has been developed that is suitable for a wide range of continuous-flow processes. Coined by our group the "Freactor" (free-to-access reactor), the new reactor integrates the efficiency of pipe-flow processing with the advanced mixing of a CSTR, delivering a general "plug-and-play" reactor platform which is well-suited to multiphasic continuous-flow chemistry. Importantly, the reactor geometry is easily customized to accommodate reactions requiring long residence times (≥3 h tested).
- Chapman, Michael R.,Kwan, Maria H. T.,King, Georgina,Jolley, Katherine E.,Hussain, Mariam,Hussain, Shahed,Salama, Ibrahim E.,González Nino, Carlos,Thompson, Lisa A.,Bayana, Mary E.,Clayton, Adam D.,Nguyen, Bao N.,Turner, Nicholas J.,Kapur, Nikil,Blacker, A. John
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p. 1294 - 1301
(2017/09/23)
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- RUTHENIUM COMPLEXES AND THEIR USES AS CATALYSTS IN PROCESSES FOR FORMATION AND/OR HYDROGENATION OF ESTERS, AMIDES AND RELATED REACTIONS
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The present invention relates to novel Ruthenium complexes of formulae A1-A4 and their use, inter alia, for (1) dehydrogenative coupling of alcohols to esters; (2) hydrogenation of esters to alcohols (including hydrogenation of cyclic esters (lactones) or cyclic di-esters (di-lactones), or polyesters); (3) preparing amides from alcohols and amines—(including the preparation of polyamides (e.g., polypeptides) by reacting dialcohols and diamines and/or polymerization of amino alcohols and/or forming cyclic dipeptides from p-aminoalcohols; (4) hydrogenation of amides (including cyclic dipeptides, polypeptides and polyamides) to alcohols and amines; (5) hydrogenation of organic carbonates (including polycarbonates) to alcohols or hydrogenation of carbamates (including polycarbamates) or urea derivatives to alcohols and amines; (6) dehydrogenation of secondary alcohols to ketones; (7) amidation of esters (i.e., synthesis of amides from esters and amines); (8) acylation of alcohols using esters; (9) coupling of alcohols with water and a base to form carboxylic acids; and (10) preparation of amino acids or their salts by coupling of amino alcohols with water and a base. The present, invention further relates to the use of certain known Ruthenium complexes for the preparation of amino acids or their salts from amino alcohols.
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Paragraph 0289
(2017/10/18)
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- Colloid and nanosized catalysts in organic synthesis: XIII. Synthesis of 2-R-2-imidazolines catalyzed by copper and iron oxide nanoparticles
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The reaction of carboxylic acids with ethylenediamine catalyzed by copper or iron oxide nanoparticles proceeds at 80°C with azeotropic water distilling off during 2-8 h to form 2-R-2-imidazolines. Acyl and diacyl derivatives of ethylenediamine are formed in the reaction as side products.
- Popov,Mokhov,Kalitina
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p. 281 - 285
(2016/04/20)
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- HIV INTEGRASE INHIBITORS
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The present invention features compounds that are HIV integrase inhibitors and therefore are useful in the inhibition of HIV replication, the prevention and/or treatment of infection by HIV, and in the treatment of AIDS and/or ARC.
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- A two-step continuous-flow synthesis of n-(2-aminoethyl)acylamides through ring-opening/hydrogenation of oxazolines
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Harnessing hydrazoic acid in flow! 2-Oxazolines can be ring-opened in a very efficient manner by treatment with in situ generated hydrazoic acid. Despite the toxic and explosive nature of hydrazoic acid, this process can be conducted safely in a continuou
- Gutmann, Bernhard,Roduit, Jean-Paul,Roberge, Dominique,Kappe, C. Oliver
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supporting information; experimental part
p. 13146 - 13150
(2012/02/02)
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- Synthesis and application of a microgel-supported acylating reagent by coupled ring-opening metathesis polymerization and activators Re-Generated by electron transfer for atom transfer radical polymerization
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A novel microgel-supported acylating reagent (MGAR) was prepared by combining ring-opening metathesis polymerization (ROMP) and Activators Re-Generated by Electron Transfer for Atom Transfer Radical Polymerization (ARGET ATRP): (1) synthesis of an ATRP macroinitiator 3 by living ROMP of oxanorbornene-based activated ester 1, derived from Af-hydroxysuccinimide, using the Grubbs initiator RuCl2(PCy3)2(=CHPh) and (Z)-but-2-ene-l,4-diyl bis(2-bromopropanoate) (BDBP) as a terminating agent; (2) synthesis of MGAR 4 by ARGET ATRP of styrene (S) and divinylbenzene (DVB) using the prepared macroinitiator 3, a CuCI2ZMe6TREN (tris[2-(dimethylamino)ethyl]amine) catalyst system, a Sn(Oct)2 [tin(II)2ethylhexanoate] reducing agent. The synthesized microgels 4 exhibit excellent acyl (acetyl, benzoyl, phenylsulfonyl) transfer properties for primary and secondary amines (n-BuNH2, Et2NH, morpholine, etc.) under mild conditions (25 °C, 13.5-14 h) affording N-acylamines with high yield (95.6-100%) and purity (94.1-96.0%).
- Li, Hong,Pang, Zi-Bo,Jiao, Zhi-Feng,Lin, Fei
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experimental part
p. 255 - 259
(2010/09/03)
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- Pyrrolo [3,2-C] Pyridine-4-One 2-Indolinone Protein Kinase Inhibitors
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The present invention relates to pyrrolo[3,2-c]pyridine-4-one 2-indolinone compounds of Formula (I) and their pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4, R5, R6, R7, R8X, Y and have the meaning cited in the specification.
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(2010/02/16)
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- Synthesis of 3-hydroxypyrid-2-ones from furfural for treatment against iron overload and iron deficiency
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Derivatives of 3-hydroxypyrid-2-ones, which posses very high affinity for iron and have anomalous applications in iron overload and iron deficiency, were prepared from furfural in simple reaction conditions.
- Samant, Bhupesh S.
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p. 1978 - 1982
(2008/12/22)
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- PYRROLO [3,2-C] PYRIDINE-4-ONE 2-INDOLINONE PROTEIN KINASE INHIBITORS
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The present invention relates to pyrrolo[3,2-c]pyridine-4-one 2-indolinone compounds of Formula (I) and their pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4, R5, R6, R7, R8 X , Y and …. have the meaning cited in the specifica
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(2010/11/28)
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- Synthesis of new bis-imidazole derivatives
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The reaction of aldimines with α-(hydroxyimino) ketones of type 10 (1,2-diketone monooximes) was used to prepare 2-unsubstituted imidazole 3-oxides 11 bearing an alkanol chain at N(1) (Scheme 2, Table 1). These products were transformed into the corresponding 2H-imidazol-2-ones 13 and 2H-imidazole-2-thiones 14 by treatment with Ac2O and 2,2,4,4-tetramethylcyclobutane-l,3-dithione, respectively (Scheme 3). The three-component reaction of 10, formaldehyde, and an alkane-1,ω-diamine 15 gave the bis[1H-imidazole 3-oxides] 16 (Scheme 4, Table2). With Ac 2O, 2,2,4,4-tetramethylcyclobutane-1,3-dithione or Raney-Ni, the latter reacted to give the corresponding bis[2H-imidazol-2-ones] 19 and 20, bis[2H-imidazol-2-thione] 21, and bis[imidazole] 22, respectively (Schemes 5 and 6). The structures of 11a and 16b were established by X-ray crystallography.
- Jasinski, Marcin,Mloston, Grzegorz,Mucha, Paulina,Linden, Anthony,Heimgartner, Heinz
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p. 1765 - 1780
(2008/02/13)
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- Pyridone azo compound, tautomer thereof, and colorant-containing curable composition, color filter and manufacturing method thereof
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The invention provides a pyridone azo compound represented by the following Formula (I) and a tautomer thereof. R1, R3 and R4 each independently represent a hydrogen atom, an alkyl group having 1 to 21 carbon atoms, an alkenyl group having 2 to 21 carbon atoms, an aryl group having 6 to 21 carbon atoms, an aralkyl group having 7 to 21 carbon atoms, or a substituent having a hetero atom; at least one of R1, R3 and R4 represents a substituent having a hetero atom; R3 and R4 may be formed into a heterocycle together with a jointly bonded nitrogen atom; and R2 represents an alkyl group having 1 to 10 carbon atoms, a methoxymethyl group, or a trifluoromethyl group. The invention further provides a colorant-containing curable composition and a color filter which contain the pyridone azo compound of Formula (I) and/or a tautomer thereof as a colorant.
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- Oligomeric aminodiol-containing compounds, libraries thereof, and process of preparing the same
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Oligomeric compounds comprising a plurality of aminodiol monomer subunits joined by linking groups are provided, as well as libraries of such compounds and processes for preparing the oligomeric compounds and libraries.
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- Substituted 2-aminoalkyl-1,4-Diaminobenzene compounds and oxidation dye precursor compositions containing same
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The oxidation hair dye precursor composition contains from 0.005 to 20.0 percent by weight of at least one coupler compound and from 0.005 to 20.0 percent by weight of at least one developer compound, which includes at least one substituted 2-aminoalkyl-1
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- Tetracyclic benzimidazole derivatives and combinatorial libraries thereof
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The present invention relates to novel tetracyclic benzimidazole derivative compounds of the following formula: wherein R1to R10have the meanings described in here. The invention further relates to combinatorial libraries containing two or more such compounds, as well as methods of preparing tetracyclic benzimidazole derivative compounds.
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- 2-aminopyridine derivatives and combinatorial libraries thereof
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The present invention relates to novel 2-aminopyridine derivative compounds of the following formula: wherein R1to R5have the meanings provided herein. The invention further relates to combinatorial libraries containing two or more such compounds, as well as methods of preparing 2-aminopyridine derivative compounds.
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- Anthraquinone anticancer drugs
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A molecule of formula (I); wherein: X is a halogen, or a substituted sulfonate group; m=1-5; n=1-5; R1, R2=H, C1-4 lower alkyl or C1-4 lower alkyl chain having additional functionality; and the amino group ?NR1R2linked to the anthraquinone is primary, secondary or tertiary or is a tertiary group in the N-oxide form having the formula —N(O)R1R2.
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- Ac2O-Py/basic alumina as a versatile reagent for acetylations in solvent-free conditions under microwave irradiation
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Acetic anhydride-pyridine over basic alumina has been used in order to carry out acetylations of hydroxy, thiol and amino groups in solvent-free conditions under microwave irradiation. The technique can be extended for selective acetylations by regulation of irradiation time.
- Paul, Satya,Nanda, Puja,Gupta, Rajive,Loupy, André
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p. 4261 - 4265
(2007/10/03)
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- High affinity chelates containing isothiocyanate groups, useful for coupling with peptides and proteins
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The ligands HBED-SCN, HBPD-SCN, and HTDD-SCN are provided which have enhanced ease of reaction with peptides or proteins and which are suitable for chelating with radioisoptopes, especially Indium-III and Gallium-67.
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- Kinetics and mechanism of aminolysis of phenyl acetates in aqueous solutions of poly(ethylenimine)
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Second-order rate constants (kn) for the aminolysis of some phenyl acetates with poly(ethylenimine) (PEI) were obtained in a pH range 4.36-11.20 at 25 °C in 1 M KC1. Linear Bronsted-type plots (log kn vs pKN of PEI) were found for less reactive esters 2-nitrophenyl acetate, 4-acetoxy-3-chlorobenzoic acid, and 4-acetoxybenzenesulfonate with slopes of 0.92, 0.99, and 0.82, respectively. Curved plots were obtained for 3-acetoxy-2,6-dinitrobenzoic acid and 4-acetoxy-3-nitrobenzene-sulfonate, which are consistent with a stepwise reaction. The most likely mechanism involves the existence of a tetrahedral intermediate (T±) and a change in the rate-determining step from its breakdown to its formation when the basicity of the polyamine increases. A semiempirical equation was used to calculate the values of limiting slopes of the plots (0.9 and 0.1 for both esters) and pKN at the center of the curvature of the plots (p-KN° = 7.94 and 9.02, respectively). The values of pKN° are lower than those estimated for the aminolysis of the same esters with simple monomeric amines (pKn° > 11) because of a better leaving ability of the aryl oxide ion from the tetrahedral intermediate when amino groups of PEI instead of simple amines are involved. Estimation of the pK's of the reactive intermediates and of the microscopic rate constants for the proton transfer from T± to PEI or from PEIH+ to T± indicates that either base or acid catalysis is unimportant in the aminolysis of these esters by PEI.
- Arcelli, Antonio,Concilio, Carlo
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p. 1682 - 1688
(2007/10/03)
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- 2-hydroxypropylamine heteroaryl ester derivatives
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The present invention relates to compounds of the general formula STR1 wherein Ar represents a substituted or unsubstituted heterocyclic group; W represents alkylene of from 1 to about 10 carbon atoms; and B represents --NR2 COR1, --NR2 CONR1 R3, --NR2 SO2 R1, NR2 SO2 NR1 R3, or --NR2 COOR1, wherein R1, R2 and R3 may be alike or different and may be hydrogen, alkyl, alkoxyalkyl cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, or aralkyl, except that R1 is not hydrogen when B is --NR2 SO2 R1 or --NR2 COOR1, or R1 and R3 may together with N form a 5 to 7 membered heterocyclic group and the pharmaceutically acceptable salts thereof. The compounds exhibit beta-adrenergic blocking activity and are also useful in the treatment of glaucoma.
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- Fiber-reactive disazo brown dye having vinylsulfone-type reactive group
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A compound, or a salt thereof, represented by the following formula, STR1 wherein A is a substituted or unsubstituted phenylene or naphthylene group, B is STR2 in which R3 is a hydrogen atom or a lower alkyl, lower alkoxy, acylamino or ureido group, and R4 is a hydrogen atom or a lower alkyl or lower alkoxy group, R1 and R3 are independently a hydrogen atom or a substituted or unsubstituted lower alkyl group, X is a substituted or unsubstituted amino, lower alkoxy, substituted phenoxy or sulfo group, Y is --SO2 CH=CH2 or --SO2 CH2 CH2 Z, in which Z is a group capable of being split by the action of an alkali, and m is 2 or 3, which is useful for dyeing hydroxyl group- or amide group-containing fiber materials to give dyed products of a brown color having excellent fastness properties with good build-up property.
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- AROMATIC AND ESTERS OF HYDROXYPROPYLAMINES
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Novel compounds of the general formula STR1 wherein Ar represents a substituted or unsubstituted aromatic or heterocyclic group; W represents alkylene of from 1 to about 10 carbon atoms; and B represents--NR 2 COR 1,--NR 2 CONR 1 R 3,--NR 2 SO 2 R. sub.1,--NR 2 SO 2 NR 1 R 3, or--NR 2 COOR 1 wherein R. sub.1, R 2 and R 3 may be the same or different and may be hydrogen, alkyl, alkoxyalkyl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, or aralkyl, except that R 1 is not hydrogen when B is--NR 2 SO 2 R 1 or--NR 2 COOR 1, or R 1 and R 3 may together with N form a 5 to 7 momoered heterocyclic group; and the pharmaceutically acceptable salts thereof. These compounds exhibit β-adrenergic blocking activity and are also useful in the treatment of glaucoma.
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- Chelating Vesicles Made from N,N-Dihexadecyl-1,2-ethanediamine-N',N'-diacetic Acid
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Aqueous suspensions of N,N-Dihexadecyl-1,2-ethanediamine-N',N'-diacetic acid (1d) give stable vesicles on sonication at pH = 3.5 and 9.0.The outer vesicle surface chelates copper(II) and iron(III) ions without vesicle precipitation.
- Fuhrhop, Juergen-Hinrich,Koesling, Volker,Schoenberger, Gerhard
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p. 1634 - 1640
(2007/10/02)
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- Ultra-Short-Acting β-Adrenergic Receptor Blocking Agents. 3. Ethylenediamine Derivatives of (Aryloxy)propanolamines Having Esters on the Aryl Function
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Various ethylenediamine derivatives have been incorporated into the nitrogen substituent of certain short-acting (aryloxy)propanolamine systems that contain esters on their aryl functions.Although several of these compounds showed durations of action comparable to their prototypes, most of the nitrogen substituents significantly prolonged the duration of β-adrenergic blockade.Similarly, while one of the compounds showed appreciable cardioselectivity in vitro, generally, little enhancement of cardioselectivity was obtained.A brief discussion of structure-activity relationships observed for the ethylenediamine derivatives is presented.
- Erhardt, Paul W.,Woo, Chi M.,Matier, William L.,Gorczynski, Richard J.,Anderson, William G.
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p. 1109 - 1112
(2007/10/02)
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- SYNTHESIS OF ACYLATED (2'-HYDROXYETHYL)AMINO- AND (2'-AMINOETHYL)AMINO-1,3,5-TRIAZINES
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The acylation of (2'-hydroxyethyl)amino-1,3,5-triazines with chloroacetyl chloride with subsequent reaction of the resulting (2'-chloroacetoxyethyl)aminotriazines with potassium thiocyanate is described.Acylated derivatives of substituted (2'-aminoethyl)aminotriazines were obtained by the reaction of the chlorotriazines with monoacylethylenediamines.
- Sapozhnikova, Zh. Z.,Prokof'eva, A. F.,Koroleva, T. I.,Mel'nikov, N. N.
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p. 205 - 208
(2007/10/02)
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