- Identification of Intermediates and Products of 2,4,6-Trimethyl-1,3,5-Hexahydrotriazine Trihydrate and Glyoxal Reaction in an Aqueous Solution by NMR Spectroscopy
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In situ formation of 2-methylimidazole as a result of 2,4,6-trimethyl-1,3,5-hexahydrotriazine trihydrate and glyoxal interaction in an aqueous solution is studied for the first time using NMR spectroscopy. In addition to the reactants and products, the reaction mixture is shown to contain stable intermediate products of the trimer decomposition as well as glycolic acid.
- Bakibaev, A. A.,Cheltygmasheva, R. S.,Fateev, A. V.,Kotelnikov, O. A.,Kotov, A. V.,Tuguldurova, V. P.,Vodyankina, O. V.
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Read Online
- Continuous synthesis method for 2-methyl-5-nitroimidazole
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The invention provides a continuous synthesis method for 2-methyl-5-nitroimidazole. The 2-methyl-5-nitroimidazole is synthesized in a micro-channel reactor. The synthesis method provided by the invention can realize continuous synthesis, is safe and stable in production process, extremely short in reaction time and high in yield, and can reduce the usage amount of concentrated sulfuric acid and lower cost.
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Paragraph 0016; 0042-0046; 0050-0054; 0058-0061; 0066-0070
(2020/07/15)
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- Imprinted Apportionment of Functional Groups in Multivariate Metal-Organic Frameworks
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Sophisticated chemical processes widely observed in biological cells require precise apportionment regulation of building units, which inspires researchers to develop tailorable architectures with controllable heterogeneity for replication, recognition and information storage. However, it remains a substantial challenge to endow multivariate materials with internal sequences and controllable apportionments. Herein, we introduce a novel strategy to manipulate the apportionment of functional groups in multivariate metal-organic frameworks (MTV-MOFs) by preincorporating interlocked linkers into framework materials. As a proof of concept, the imprinted apportionment of functional groups within ZIF-8 was achieved by exchanging imine-based linker templates with original linkers initially. The removal of linker fragments by hydrolysis can be achieved via postsynthetic labilization, leading to the formation of architectures with controlled heterogeneity. The distributions of functional groups in the resulting imprinted MOFs can be tuned by judicious control of the interlocked chain length, which was further analyzed by computational methods. This work provides synthetic tools for precise control of pore environment and functionality sequences inside multicomponent materials.
- Feng, Liang,Wang, Kun-Yu,Lv, Xiu-Liang,Powell, Joshua A.,Yan, Tian-Hao,Willman, Jeremy,Zhou, Hong-Cai
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supporting information
p. 14524 - 14529
(2019/10/02)
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- Novel nitroimidazole drug as well as preparation method and application of novel nitroimidazole drug
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The invention relates to a novel nitroimidazole compound as well as a preparation method and application of the novel nitroimidazole compound to medical science and specifically relates to a nitroimidazole compound as shown in a general formula (I), a preparation method of the nitroimidazole compound and a pharmaceutical composition containing the compound. The invention aims at synthesizing a novel compound of a series of nitroimidazole derivatives by modifying the structure of a nitroimidazole compound, the compound can be used for obviously reducing adverse reaction in clinic, meanwhile, the compound has a relatively ideal effect on protecting the liver and kidneys, and the clinical application of the compound is apparent.
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Paragraph 0020
(2018/04/01)
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- Design, synthesis, structure-activity relationships study and X-ray crystallography of 3-substituted-indolin-2-one-5-carboxamide derivatives as PAK4 inhibitors
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We have previously described the identification of indolin-2-one-5-carboxamides as potent PAK4 inhibitors. This study expands the structure-activity relationships on our original series by presenting several modifications in the lead compounds, 2 and 3. A series of novel derivatives was designed, synthesized, and evaluated in biochemical and cellular assay. Most of this series displayed nanomolar biochemical activity and potent antiproliferative activity against A549 and HCT116 cells. The representative compound 10a exhibited excellent enzyme inhibition (PAK4 IC50 = 25 nM) and cellular potency (A549 IC50 = 0.58 μM, HCT116 IC50 = 0.095 μM). An X-ray structure of compound 10a bound to PAK4 was obtained. Crystallographic analysis confirmed predictions from molecular modeling and helped refine SAR results. In addition, Compound 10a displayed focused multi-targeted kinase inhibition, good calculated drug-likeness properties. Further profiling of compound 10a revealed it showed weak inhibitory activity against various isoforms of human cytochrome P450.
- Guo, Jing,Zhao, Fan,Yin, Wenbo,Zhu, Mingyue,Hao, Chenzhou,Pang, Yu,Wu, Tianxiao,Wang, Jian,Zhao, Dongmei,Li, Haitao,Cheng, Maosheng
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p. 197 - 209
(2018/06/12)
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- Coordination properties of μ-carbidodimeric iron(IV) 2,3,7,8,12,13,17,18-octapropyltetraazaporphyrinate and 5,10,15,20-tetraphenylporphyrinate in reactions with nitrogen-containing bases
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The equilibria of μ-carbidodimeric iron(IV) 2,3,7,8,12,13,17,18-octapropyltetraazaporphyrinate and 5,10,15,20-tetraphenylporphyrinate in reactions with nitrogen-containing bases in an inert solvent were studied spectrophotometrically. The equilibrium constants of the studied processes and the compositions of molecular complexes were determined. The effect of the electronic and conformation factors of a macrocycle and the nature of the base on the equilibrium constant was pointed out. A comparative analysis of the substrate specificity of the studied compounds was performed.
- Zaitseva,Zdanovich,Kudrik,Koifman
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p. 1257 - 1266
(2017/09/29)
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- A highly efficient gas-dominated and water-resistant flame retardant for non-charring polypropylene
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Traditional phosphorus-nitrogen (P-N) flame-retardant systems for polypropylene (PP) always act through joint action of the gaseous phase and condensed phase, and are accompanied with a decrease of the thermal stability and water resistance. In this work, a novel mono-component and gas-dominated flame retardant, named DPPIP, was prepared through an amidation reaction of diphenylphosphinyl chloride and piperazine, and used to flame retard PP. Experimental results confirmed that both the thermal stability and water resistance of PP/DPPIP were improved. The initial thermal decomposition temperature of PP/25 wt% DPPIP at 5 wt% weight loss was 287.5 °C under air atmosphere, which is higher than that of neat PP (266.1 °C). Besides, a water-resistance test verified that PP/25 wt% DPPIP had a weight loss of only about 0.52 wt%. More importantly, the flame retardant ability of PP/25 wt% DPPIP had been greatly improved, passing the V-0 rating (UL-94). Furthermore, after the water-resistance test, the LOI value of PP/25 wt% DPPIP exhibited nearly no difference and still passed the UL-94 V-0 rating. A cone calorimeter (CC) result indicated that DPPIP had a positive effect on inhibiting heat release of PP during combustion. All of these combustion tests displayed that there was no char left. The flame retardant mechanism of DPPIP was investigated with py-GC/MS and TG-FTIR. The results illustrated that the gaseous phase resulting from the thermal decomposition of DPPIP played the leading role in the self-extinguishing behavior of PP/DPPIP, which consisted of a large amount of inflammable gaseous products such as piperazine and its derivatives, and phosphorus-containing structures.
- Shao, Zhu-Bao,Zhang, Ming-Xin,Han, Ye,Yang, Xu-Dong,Jin, Jing,Jian, Rong-Kun
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p. 51919 - 51927
(2017/11/22)
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- Enhanced nonenzymatic RNA copying with 2-aminoimidazole activated nucleotides
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Achieving efficient nonenzymatic replication of RNA is an important step toward the synthesis of self-replicating protocells that may mimic early forms of life. Despite recent progress, the nonenzymatic copying of templates containing mixed sequences remains slow and inefficient. Here we demonstrate that activating nucleotides with 2-aminoimidazole results in superior reaction kinetics and improved yields of primer extension reaction products. This new leaving group significantly accelerates monomer addition as well as trimer-assisted RNA primer extension, allowing efficient copying of a variety of short RNA templates with mixed sequences.
- Li, Li,Prywes, Noam,Tam, Chun Pong,Oflaherty, Derek K.,Lelyveld, Victor S.,Izgu, Enver Cagri,Pal, Ayan,Szostak, Jack W.
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supporting information
p. 1810 - 1813
(2017/02/15)
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- METHOD FOR PRODUCING 1,2-DISUBSTITUTED IMIDAZOLE
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PROBLEM TO BE SOLVED: To provide a 1,2-disubstituted imidazole production method which can suppress production of by-products and efficiently produce high-purity 1,2-disubstituted imidazole in a shorter reaction time than that of the conventional one. SOLUTION: A 1,2-disubstituted imidazole production method includes a first stage reaction step of reacting an aldehyde compound with ammonia and/or a primary amine, and a second stage reaction step of reacting a glyoxal compound and ammonia and/or a primary amine with reaction products in the first stage reaction step. The primary amine is reacted in at least one of the first stage reaction step and the second stage reaction step to produce 1,2-disubstituted imidazole in a flow manner. The reaction in at least one of the first stage reaction step and the second stage reaction step is performed in a pressurized state at a pressure of 1-50 MPa. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2017,JPOandINPIT
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Paragraph 0051-0052
(2017/06/14)
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- Reduction of (chloro)-μ-nitrido-bis[(tetra-tert-butyl-phthalocyaninato)iron(IV)] with organic N-bases
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The interaction of (chloro)-μ-nitrido-bis[(tetra-Tert-butyl-phthalocyaninato)iron(IV)] Cl(FePc)2N with organic N-bases L as electron-donors (L diethylamine, imidazole, 1-methylimidazole, 2-methylimidazole) with the formation of one-electron reduced species (L)PcFeIII-N?FeIVPc(L) was investigated in benzene at 298 K by UV-visible spectroscopy. The reaction was established to be stepwise process including fast reversible axial binding of two substrate molecules onto iron cations followed by slow one-electron metal-centered reduction. The results of IR, ESI-MS and EPR study support the formation of final product with Fe?3-N?Fe?4 unit and two substrate molecules in the first coordination sphere. The reaction kinetics was studied, the pre-equilibrium constants Keq and rate constants κ were obtained. The Keq and κ values were found to be linearly correlated with basicity of substrates pκa. The possibility of the transition Fe4?→Fe3??is promoted by electron-donor properties of substrate combined with the presence of both electron-rich macrocycle and φ-backdonation Fe →NPc.
- Zaitseva, Svetlana V.,Zdanovich, Sergei A.,Tyulyaeva, Elena Y.,Grishina, Ekaterina S.,Koifman, Oskar I.
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p. 639 - 646
(2016/07/11)
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- A practical and highly efficient reductive dehalogenation of aryl halides using heterogeneous Pd/AlO(OH) nanoparticles and sodium borohydride
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The reductive dehalogenation of aryl halides was performed by using commercially available aluminium oxy-hydroxide-supported palladium (Pd/AlO(OH)) nanoparticles of about 3?nm size (0.5?wt.?% Pd) with sodium borohydride. The dehalogenated products were obtained with absolute conversion in a mixture of H2O/MeOH (v/v=1/1) under ultrasonic conditions at room temperature. All aryl halides were successfully converted to halogen-free compounds within 1.5–4?h with yields of over 95%. The one-pot catalytic method is presented as a new process for the reductive dehalogenation of halogenated compounds. This method is quite simple, highly efficient and eco-friendly, and has an exceptional recovery rate.
- Kara, Belguzar Yasemin,Yazici, Melike,Kilbas, Benan,Goksu, Haydar
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p. 5898 - 5902
(2016/09/07)
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- Coordinating ability of rhodium(III) porphyrins toward organic bases
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Reactions of hydroxo(2,3,7,8,12,13,17,18-octaethylporphyrinato)rhodium(III) and acetylacetato-(5,10,15,20-tetraphenylporphyrinato)rhodium(III) with nitrogen-containing substrates were studied by spectrophotometry. The stability constants and compositions of the resulting molecular complexes were determined, and the effects of the macrocycle nature and substrate basicity on the stability constants were estimated. The structures of the isolated rhodium porphyrin molecules and their complexes with organic bases were optimized by the PM3 quantum chemical method. The degree of macrocycle deformation was found to change in the course of metal-substrate coordination. A correlation between the metal-substrate bond energy and equilibrium constant was revealed.
- Zaitseva,Zdanovich,Bryukhanova,Koifman
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p. 2786 - 2792
(2016/02/18)
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- Deprotection of N-benzylbenzimidazoles and N-benzylimidazoles with triethylsilane and Pd/C
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The benzyl group is a protecting group for benzimidazoles and imidazoles that can survive acidic, basic, oxidizing, and reducing conditions. Deprotection, however, can require vigorous and potentially non-chemoselective methods. The triethylsilane–Pd/C reduction system is an exceptionally mild, convenient, and efficient method for deprotecting N-benzylbenzimidazoles that are unsubstituted at the 2- and 4-positions as well as suitably substituted N-benzylimidazoles.
- Graham, Thomas H.
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supporting information
p. 2688 - 2690
(2017/11/14)
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- Synthesis, structure-activity relationship studies, and identification of novel 5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine derivatives as dual orexin receptor antagonists. Part 1
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A novel series of non-peptidic OX1R/OX2R orexin receptor antagonists was prepared by heterocyclic replacement of the dimethoxyphenyl moiety contained in the tetrahydroisoquinoline core skeleton of almorexant. Introduction of substituted imidazole moieties delivered potent dual orexin receptor antagonists with nanomolar potency for hOX1R and hOX2R suitable for further fine-tuning. The preparation of these novel orexin receptor antagonists and the outcome of preliminary structure-activity relationship studies are described in this communication.
- Sifferlen, Thierry,Koberstein, Ralf,Cottreel, Emmanuelle,Boller, Amandine,Weller, Thomas,Gatfield, John,Brisbare-Roch, Catherine,Jenck, Francois,Boss, Christoph
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p. 2212 - 2216
(2013/04/23)
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- Unusual reactivity of N-tert-butylimines under FVT conditions
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Thermal reactions of N-tert-butyl-(E)-crotonaldimine (1a) and 1,4-di-(tert-butyl)-1,4-diazabuta-1,3-dien (glyoxal-bis-N-tert-butylimine) (1b) under FVT conditions have been studied. It has been found that at 800 °C compound 1a yielded pyrrole and crotonon
- Le?niak, Stanis?aw,Pasternak, Beata,Justyna, Katarzyna,Vu, Thien Y.,Huynh, Thi Kieu Xuan,Khayar, Sa?d,Dargelos, Alain,Chrostowska, Anna
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p. 722 - 729
(2013/07/27)
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- Fluorous oxime palladacycle: A precatalyst for carbon-carbon coupling reactions in aqueous and organic medium
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To facilitate precatalyst recovery and reuse, we have developed a fluorous, oxime-based palladacycle 1 and demonstrated that it is a very efficient and versatile precatalyst for a wide range of carbon-carbon bond formation reactions (Suzuki-Miyaura, Sonogashira, Stille, Heck, Glaser-type, and Kumada) in either aqueous or organic medium under microwave irradiation. Palladacycle 1 could be recovered through F-SPE in various coupling reactions with recovery ranging from 84 to 95% for the first cycle. Inductively coupled plasma optical emission spectrometry (ICP-OES) analyses of the Pd content in the crude product from each class of transformation indicated extremely low levels of leaching and the palladacycle could be reused four to five times without significant loss of activity.
- Susanto, Woen,Chu, Chi-Yuan,Ang, Wei Jie,Chou, Tzyy-Chao,Lo, Lee-Chiang,Lam, Yulin
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experimental part
p. 2729 - 2742
(2012/05/21)
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- Rapid and efficient biomimetic oxidation of 2-imidazolines to their corresponding imidazoles with NaIO4 catalyzed by Mn(salophen)Cl
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Rapid and efficient oxidation of 2-substituted imidazolines with sodium periodate is reported. The Mn(III)-salophen/NaIO4 catalytic system efficiently converted 2-imidazolines to their corresponding imidazoles at room temperature in 2: 1, CH3CN/H2O mixture.
- Kargar, Hadi
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experimental part
p. 863 - 866
(2011/06/25)
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- Dehydrogenation of 2-imidazolines with sodium periodate catalyzed by manganese(III) tetraphenylporphyrin
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In the present work, dehydrogenation of 2-substituted imidazolines with sodium periodate in the presence of tetraphenylporphyrinatomanganese(III) chloride, [Mn(TPP)Cl], is reported. A wide variety of 2-imidazolines efficiently converted to their corresponding imidazoles by [Mn(TPP)Cl]/NaIO4 catalytic system at room temperature in 1:2, CH3CN/H2O mixture. The effect of reaction parameters such as kind of solvent and catalyst amount was also investigated.
- Kargar, Hadi,Moghadam, Majid,Mirkhani, Valiollah,Tangestaninejad, Shahram,Mohammadpoor-Baltork, Iraj,Nameni, Iman
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experimental part
p. 2146 - 2148
(2011/04/24)
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- Oxidation of 2-imidazolines to 2-imidazoles with sodium periodate catalyzed by polystyrene-bound manganese(III) porphyrin
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In the present work, the dehydrogenation of 2-substituted imidazolines with sodium periodate in the presence of tetraphenylporphyrinatomanganese(III) chloride supported on polystyrene-bound imidazole, [Mn(TPP)Cl@PSI] is reported. A wide variety of 2-imidazolines were efficiently converted to their corresponding imidazoles by the [Mn(TPP)Cl@PSI]/NaIO4 catalytic system in a 1:2 CH3CN/H2O mixture under agitation with magnetic stirring. Ultrasonic irradiation enhanced the catalytic activity of this catalyst in the oxidation of 2-imidazolines and this led to shorter reaction times and higher product yields. This catalyst could be reused several times without significant loss of its catalytic activity.
- Kargar, Hadi,Moghadam, Majid,Mirkhani, Valiollah,Tangestaninejad, Shahram,Mohammadpoor-Baltork, Iraj,Naghipour, Mahmood
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experimental part
p. 1463 - 1468
(2011/06/27)
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- A convenient procedure for preparing hetarylamides and their analogs by dehydrogenation of the corresponding imidazoles
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Conditions of aromatization of 2-(2-hetaryl)imidazolines and their analogs with various dehydrogenating agents were examined. A new catalytic system, Pd/C-diphenyl oxide, was studied, and the optimal catalyst:imidazoline ratio ensuring formation of 2-substituted imidazoles in high yield was found.
- Aleksandrov,El'Chaninov
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experimental part
p. 1024 - 1026
(2011/01/05)
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- PATTERNED FINE PARTICLE FILM STRUCTURES
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A patterned fine particle film structure includes a fine particle layer including fine particles arranged and bound to a surface of a substrate coated with a patterned film including a first film compound having a first functional group. The fine particles are coated with films including a first coupling agent having a first coupling reactive group that undergoes a coupling reaction with the first functional group to form a bond. The fine particle layer is bound by a bond formed through a coupling reaction. In an embodiment, fine particles coated with films of a film compound that reacts with the first coupling reactive group and the fine particles are alternately bound to the substrate.
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- Metal-free oxidative dehydrogenation of imidazolines and pyrazolines using silica-adsorbed peroxymonosulfate under aprotic and almost neutral conditions
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Oxidative dehydrogenation of 1,3,5-trisubstituted pyrazolines and 2-substituted imidazolines to their corresponding pyrazoles and imidazoles is carried out effectively by treatment with benzyltriphenylphosphonium peroxymonosulfate as an oxidant silica-adsorbed under aprotic and almost neutral conditions.
- Adibi,Hajipour,Jafari
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experimental part
p. 802 - 806
(2009/04/06)
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- Synthesis of enantiopure 1-substituted, 1,2-disubstituted, and 1,4,5-trisubstituted imidazoles from 1,2-amino alcohols
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A highly versatile method for the preparation of enantiopure 1-substituted, 1,2-disubstituted, and 1,4,5-trisubstituted imidazoles was developed by using the cyclocondensation reaction of a 1,2-dicarbonyl compound, an aldehyde, a 1,2-amino alcohol, and ammonium acetate.
- Matsuoka, Yuki,Ishida, Yasuhiro,Sasaki, Daisuke,Saigo, Kazuhiko
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p. 8199 - 8206
(2007/10/03)
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- Mild, efficient, and chemoselective dehydrogenation of 2-imidazolines, bis-imidazolines, and N-substituted-2-imidazolines with potassium permanganate supported on montmorillonite K-10
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Different types of 2-imidazolines, bis-imidazolines, and N-substituted-2-imidazolines are efficiently oxidized to their corresponding imidazoles with potassium permanganate (KMnO4) supported on montmorillonite K-10 under very mild conditions. The procedure is very simple and no strict conditions were required. Selective dehydrogenation of 2-alkyl-2-imidazolines in the presence of 2-aryl-2-imidazolines is a noteworthy advantage of this method and can be considered as a useful practical achievement in these reactions.
- Mohammadpoor-Baltork, Iraj,Abdollahi-Alibeik, Mohammad
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p. 110 - 114
(2007/10/03)
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- MANUFACTURING METHOD OF 1-SUBSTITUTED IMIDAZOLE COMPOUND
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PROBLEM TO BE SOLVED: To provide a high-yield manufacturing method of a 1-substituted imidazole compound which is expected to be useful as a curing agent for epoxy resins, polyurethane resins or the like, as an intermediate of various agrochemicals, antibiotics or pharmaceuticals such as anti-AIDS agents or the like, or as dye intermediates. SOLUTION: An aldehyde compound is reacted with a primary amine to give an imine compound, and subsequently an α,β-dicarbonyl compound and ammonia are added and allowed to react with the imine compound. Preferably, the α,β-dicarbonyl compound and ammonia are simultaneously added.
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- Alumina supported potassium permanganate: An efficient reagent for chemoselective dehydrogenation of 2-imidazolines under mild conditions
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An efficient method for the oxidation of 2-imidazolines to their corresponding imidazoles using KMnO4/Al2O3 under very mild reaction conditions is reported. Selective oxidation of 2-alkylimidazolines was also performed in the presence of 2-arylimidazolines and other functional groups such as sulfide, ether, aldehyde, acetal and THP ether. Potassium permanganate supported on alumina was found to be an efficient reagent system for dehydrogenation of 2-imidazolines to imidazoles under mild conditions at room temperature. Selective oxidation of 2-alkylimidazolines in the presence of 2-arylimidazolines was achieved using this reagent system. 2-Imidazolines were also selectively converted to their corresponding imidazoles in the presence of other oxidizable functional groups such as sulfide, ether, aldehyde, acetal and THP ether. The oxidation procedure described here is easy to carry out and does not require strict reaction conditions.
- Abdollahi-Alibeik, Mohammad,Mohammadpoor-Baltork, Iraj,Zolfigol, Mohammad Ali
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p. 6079 - 6082
(2007/10/03)
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- Novel, mild and chemoselective dehydrogenation of 2-imidazolines with trichloroisocyanuric acid
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A rapid, mild and high-yielding method for dehydrogenation of a variety of structurally diverse 2-imidazolines to imidazoles jusing trichloroisocyanuric acid (TCCA) in the presence of DBU is reported. Chemoselective oxidation of 2-imidazolines can be achieved in the presence of sulfide and alcohol. The mild conditions of this procedure and the absence of any transition metal make this reaction suitable for safe laboratory use.
- Mohammadpoor-Baltork, Iraj,Zolfigol, Mohammad Ali,Abdollahi-Alibeik, Mohammad
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p. 2803 - 2805
(2007/10/03)
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- Novel and chemoselective dehydrogenation of 2-substituted imidazolines with potassium permanganate supported on silica gel
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Various types of 2-imidazolines are efficiently oxidized to the corresponding imidazoles using potassium permanganate supported on silica gel under mild conditions at room temperature. 2-Alkylimidazolines are selectively converted to their corresponding imidazoles in the presence of 2-arylimidazolines. Chemoselective oxidation of 2-imidazolines in the presence of other oxidizable functional groups such as sulfide, ether, aldehyde, acetal, and THP ether was also achieved by this reagent system.
- Mohammadpoor-Baltork, Iraj,Zolfigol, Mohammad Ali,Abdollahi-Alibeik, Mohammad
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p. 8687 - 8690
(2007/10/03)
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- Thermal degradation of ionic liquids at elevated temperatures
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Ionic liquids based on the imidazolium cation are found to degrade, yielding volatile degradation products, at temperatures significantly lower than previously reported and thus a parameter Tz/x (the maximum operating temperature) is developed to provide a more appropriate estimate of thermal stability.
- Baranyai, Krisztian J.,Deacon, Glen B.,MacFarlane, Douglas R.,Pringle, Jennifer M.,Scott, Janet L.
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p. 145 - 147
(2007/10/03)
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- An efficient method for the N-debenzylation of aromatic heterocycles
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The treatment of N-benzylated heterocycles with potassium tert-butoxide/DMSO and oxygen at room temperature cleanly affords N-debenzylated products in high yield. This procedure can be utilized on a variety of functionalized nitrogen-containing heterocycles such as imidazoles, benzimidazoles, pyrazoles, indazoles, carbazoles, and indoles.
- Haddach, Aubrey A.,Kelleman, Audrey,Deaton-Rewolinski, Melissa V.
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p. 399 - 402
(2007/10/03)
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- Benzothiazole derivatives with activity as adenosine receptor ligands
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The present invention relates to substituted benzothiazole derivitives and to their pharmaceutically acceptable salts useful for the treatment of diseases related to the adenosine receptor.
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- Hydrolysis of N-cyanoazoles
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The hydrolysis kinetics of N-cyanoazoles in alkaline solutions is described by a first-order kinetic equation with respect to the substrate and concentration of hydroxide ions. The hydrolysis rate constants increase with increasing number of nitrogen atoms in the heterocyclic moiety and decrease with introduction of the annelated benzene ring.
- Pan'kov,Belyakova,Vishnyakov,Purygin
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p. 763 - 766
(2007/10/03)
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- Color developing agent, processing composition and color image-forming method
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A method for forming a color image comprises the step of developing an image-wise exposed silver halide color photographic photosensitive material at the presence of a 6-aminotetrahydroquinoline color developing agent which is the following compound or its analoge. According to this method, the rapid process can be attained and an image of a low fog density can be obtained. STR1
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- 1H and 31P NMR study of ADP and GDP spontaneous synthesis from 2-methylimidazole-activated AMP and GMP nucleotides and inorganic phosphate
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1H and 31P NMR data show that adenosine 5′-(2-methylimidazol-1-ylphosphonate) (2-MeImpA) and guanosine 5′-(2-methylimidazol-1-ylphosphonate) (2-MeImpG), known as possible prebiotic precursors of polynucleotides, produce the corresponding diphosphonucleotides in sodium phosphate solution at pD 7.6. Phosphate ions also enhance the hydrolysis of these molecules by activating a water molecular associated as a weak complex with the phosphoryl moiety of 2-MeImpA and 2-MeImpG. A kinetic study was done by quantitative 1H NMR spectroscopy and mechanistic hypotheses were tested by semiempirical PM3 modelling.
- Pereira, Jose,Cadete, Ana
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p. 1143 - 1148
(2007/10/03)
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- Adduct of bisepoxy compound and P-guanamine
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The invention pertains to an adduct obtainable by condensation of a bisepoxy compound and a P-guanamine according to the formula wherein X is CR3R4-(CR1R2)n-CR5R6or o-phenylidene, n is 0 or 1, and R1- R8may be the same or different and represent H, methyl or ethyl, and the molar ratio P-guanamine : bisepoxide is 0.60 to 0.35. The adduct is used in the manufacture of synthetic materials, notably printed wiring boards (PWBs).
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- Tetrasubstituted imidazoles
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A compound of the formula STR1 wherein the substituents are defined in the specification useful for the treatment of cardiovascular disorders.
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- Method of preventing abnormal stimulation of AT1 and AT2 receptors
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Products of formula (1), wherein R1 is particularly STR1 alkyl, alkylthio or alkoxy; R2 is particularly halogen, --S--R, --O--R or --C(OH)(R)--COOH, where R is alkyl or alkenyl; R3 is particularly carboxy, acyl, halogen, alkyl, alkenyl or alkylthio; and R4 is particularly --(CH2)m1 --COOR4, --(CH2)m1 --CONHR14, --(CH2)m1 --CN, --SO2 --NH--SO2 --R14, 13 NH--SO2 --R14, --PO3 R14, or --NH--SO2 --CF3, where m1 is 0-4 and R14 is hydrogen, alkyl or alkenyl; are useful for preparing pharmaceutical compositions for treating disorders resulting from abnormal stimulation of angiotensin II receptors AT1 and AT2.
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- 1H-IMIDAZOLE PREPARATION VIA PERMANGANATE DEHYDROGENATION OF 2-IMIDAZOLINES
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Permanganate and manganate ions were evaluated as dehydrogenating agents in the conversion of 2-substituted 2-imidazolines into the corresponding 2-substituted imidazoles.It was found that permanganate ion in dry dioxane efficiently performs this transformation rendering this method competitive with related procedures.
- Campos, Elena Ma.,Jimenez, Rogelio,Martinez, Flor,Salgado, Hector
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p. 841 - 850
(2007/10/02)
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- Pt/Al2O3 CATALYSTS IN THE SYNTHESIS OF NITROGEN HETEROCYCLES. CATALYTIC SYNTHESIS OF PYRAZINES
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A study was carried out on the use of Pt/Al2O3 catalysts in the synthesis of pyrazines via the dehydrogenation of piperazines, dehydrodeamination of diamines, and dehydrocyclocondensation of N-hydroxyalkyldiamines.In contrast to the current hypothesis of the intermediate formation of piperazine in the latter two reactions, evidence was found that these reactions proceed through initial dehydrogenation and the dehydrogenated intermediate then undergoes cyclization.Polyalkylpyrazines, formed by the alkylation of the pyrazine ring by hydrogenolysis products, are the major side-products in all the reactions studied.Pyrazines may be obtained in high yield and satisfactory selectivity by selecting suitable modifiers, which enhance the dehydrogenation activity of the catalyst and suppress the hydrogenolysis of the C-N bond.
- Gitis, K. M.,Neumoeva, G. E.,Isagulyants, G. V.
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p. 1308 - 1315
(2007/10/02)
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- A Retro-Diels-Alder Approach to Oxazoles and Imidazoles
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Heating N-acyl derivatives 4 of 3-endo-aminobicyclohept-5-en-2-endo-ol (3) at 185-195 deg C for 4-5 h provides oxazoles 1a-e in 49-88percent yields.The reaction proceeds via an initial dehydration to an oxazoline which undergoes retro-Diels-Alder reaction to provide the oxazole.Similarly, imidazoles 7a-f may be obtained in 40-79percent yields by heating imidazolines 6a-f to effect the cycloreversion.
- Eissenstat, Michael A.,Weaver, John D.
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p. 3387 - 3390
(2007/10/02)
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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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p. 895 - 898
(2007/10/02)
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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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p. 1551 - 1554
(2007/10/02)
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- CATALYTIC SYNTHESIS OF C-ALKYLIMIDAZOLES OVER PLATINUM-ALUMINA CATALYSTS
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The synthesis of C-alkylimidazoles from 1,2-diamines and carboxylic acids over bifunctional platinum-alumina catalysts has been studied.It has been shown that this method is effective for the synthesis of 2-alkyl and 2,4-dialkylimidazoles including imidazoles with long-chain alkyls.The effect of the reaction temperature, space velocity of the flow of the raw materials, and dilution by hydrogen on the yield of product has been examined for the example of the synthesis of 2-methylimidazole from ethylenediamine and acetic acid, and the stability of the catalyst in continuous reaction cycles with intermediate oxidative regeneration has been studied.The composition of the accompanying products has been established and a mechanism proposed for their formation.Keywords: bifunctional catalyst, platinum-alumina catalyst, alkylimidazoles, 2-methylimidazole.
- Gitis, K. M.,Neumoeva, G. E.,Raevskaya, N. I.,Arutyunyants, G. A.,Isagulyants, G. V.
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p. 728 - 734
(2007/10/02)
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- ACETYLENIC IMIDAZOLES HAVING CENTRAL NERVOUS SYSTEM ACTIVITY
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Acetylenic imidazole compounds having cholinergic agonist or antagonist activity useful in the treatment of mental disorders, extrapyramidal motor disorders, disorders of the parasympathetic nervous system and glaucoma or as analgesics for the treatment of pain. Typical central nervous system disorders for which the subject compounds can be used include cognitive disorders of all ages, including senile dementia, Alzheimer's disease and other related disorders. The compounds are particularly developed to improve mental performance when a mental deficiency is diagnosed.
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- EFFECT OF THE SURFACE AREA OF PLATINUM ON THE ACTIVITY OF A BIFUNCTIONAL ALUMINOPLATINUM CATALYST IN THE SYNTHESIS OF ALKYLIMIDAZOLES FROM DIAMINES AND CARBONYL ACIDS
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An investigation has been conducted into the effect of the acid and dehydrogenating functions of an aluminoplatinum catalyst on the synthesis of 2-methylimidazole from ethylenediamine and acetic acid.It has been established that formation of the intermediate 2-methylimidazoline involves the acid Al2O3 centers and its rate of formation is greater than the rate of its subsequent dehydrogenation to 2-methylimidazole on the Pt centers.The symbatic nature of the variations in the 2-methylimidazole yield and the surface area of the platinum in the aluminoplatinum catalyst has been demonstrated.Keywords: C-alkylimidazoles, 2-methylimidazole, aluminoplatinum catalyst.
- Gitis, K. M.,Raevskaya, N. I.,Zaitsev, A. V.,Borovkov, V. Yu.,Kozan, S. B.,Isagulyants, G. V.
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p. 1547 - 1550
(2007/10/02)
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- DEHYDROGENATION OF PIPERAZINE INTO PYRAZINE ON ALUMINA-PLATINUM CATALYSTS
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Dehydrogenation of piperazine on alumina-platinum catalysts at 360-400 deg C was investigated.It was found that the alumina-platinum catalyst has low selectivity in the formation of pyrazine (yield /= 43percent), and dehydrogenation is accompanied by decomposition and coke formation and products of decomposition in the formation of alkylpyrazines.The alumina-platinum catalyst in In2O3 and Re2O7 additives permits obtaining pyrazine with a yield of up to 80percent.Dehydrogenation of piperazine is accompanied by reactions of decomposition, dehydroisomerization, and alkylation to a small degree, resulting in the formation of pyrrole, methylimidazole, and alkylpyrazines.
- Isagulyants, G. V.,Gitis, K. M.,Myasnikov, V. A.,Neumoeva, G. E.
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p. 1340 - 1345
(2007/10/02)
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- 1,2- and 1,3-Diamine Exchange between Substituted 4,5-Dihydroimidazoles and 1,4,5,6-Tetrahydropyrimidines: Routes to Benzimidazoles, Dihydroimidazoles, and Tetrahydropyrimidines
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A range of 2-substituted 4,5-dihydroimidazoles and 2-substituted 1,4,5,6-tetrahydropyrimidines when heated with an excess of substituted ethane-1,2-diamines, o-phenylenediamines, and propane-1,3-diamine underwent diamine exchange to give 2-substituted heterocycles derived from the solvent diamine.The reaction was an equilibrium process favouring six-membered rings.The synthetic scope is amplified by the ready aromatisation of these partially reduced heterocycles.
- Butler, Richard N.,Fitzgerald, Kevin J.
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p. 155 - 157
(2007/10/02)
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- Magnesium Ion Catalyzed P-N Bond Hydrolysis in Imidazolide-Activated Nucleotides. Relevance to Template-Directed Synthesis of Polynucleotides
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Magnesium, an ion necessary in enzymatic as well as in nonenzymatic template-directed polynucleotide-synthesizing reaction, has been found to catalyze the hydroxide ion attack on the P-N bond of selected 5'-monophosphate imidazolide derivatives of nucleotides, such as guanosine 5'-monophosphate 2-methylimidazolide (2-MeImpG), guanosine 5'-monophosphate imidazolide (ImpG), and adenosine 5'-monophosphate 2-methylimidazolide (2-MeImpA).Calcium ion behaves similarly, but quantitatively the effects are smaller.Pseudo-first-order rate constants of 2-MeImpG and ImpG hydrolysis as a function of Mg(2+) concentration have been obtained in the range 6 +/-, imidazolide moiety protonated) with OH(1-) rather than reaction of the anionic form (S(1-), imidazolide moiety deprotonated) with water.This conclusion is based on a study of the N-methylated substrates N-MeImpG and 1,2-diMeImpG, respectively, which were generated in situ by the equilibrium reaction of ImpG with N-methylimidazole and 2-MeImpG with 1,2-dimethylimidazole, respectively.In contrast, in the absence of Mg(2+) the reaction of S(1-) with water competes with the reaction of SH+/- with OH(1-).The present study bears on the mechanism of the Mg(2+)-catalyzed template-directed synthesis of oligo- and polynucleotides derived from 2-MeImpG and on thecompetition between oligonucleotide synthesis and hydrolysis of 2-MeImpG.
- Kanavarioti, Anastassia,Bernasconi, Claude F.,Doodokyan, Donald L.,Alberas, Diann J.
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p. 7247 - 7257
(2007/10/02)
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