- Visible Light-Promoted Aryl Azoline Formation over Mesoporous Organosilica as Heterogeneous Photocatalyst
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N-heterocyclic compounds demonstrate wide applications ranging from natural compound production to coordination chemistry. Usually, the synthesis of N-heterocyclic compounds is conducted under thermal conditions, mostly by Lewis acids or metal-containing compounds as molecular catalysts. Here, we report a photocatalytic route for aryl azoline formation by mesoporous organosilica as visible light-active and heterogeneous photocatalyst. Via formation of aromatic aldehydes with various amines, 2-phenyl-2-imidazoline, 2-phenyl-2-oxazoline, 2-phenyl-2-thiazoline and their derivatives could be formed with high conversion and selectivity. Additionally, the organosilica photocatalyst showed high stability and reusability.
- Wei, Wenxin,Li, Run,Huber, Niklas,Kizilsavas, G?nül,Ferguson, Calum T. J.,Landfester, Katharina,Zhang, Kai A. I.
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p. 3410 - 3413
(2021/05/29)
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- Full Cleavage of C≡C Bond in Electron-Deficient Alkynes via Reaction with Ethylenediamine
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Reaction of 1,2-diaminioethane (ethylenediamine) with electron-deficient alkynes leads to full scission of the C≡C bond even in the absence of a keto group directly attached to the alkyne. This process involves oxidation of one of the alkyne carbons into C2 of a 2-R-4,5-dihydroimidazole with the concomitant reduction of the other carbon to a methyl group. The sequence of Sonogashira coupling with the ethylenediamine-mediated fragmentation described in this work can be used for selective formal substitution of halogen in aryl halides by a methyl group or a 4,5-dihydroimidazol-2-yl moiety.
- Vasilevsky, Sergei F.,Davydova, Maria P.,Mamatyuk, Victor I.,Tsvetkov, Nikolay,Hughes, Audrey,Baranov, Denis S.,Alabugin, Igor V.
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p. 421 - 429
(2017/04/07)
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- Synthesis of benzimidazole and quinoxaline derivatives using reusable sulfonated rice husk ash (RHA-SO3H) as a green and efficient solid acid catalyst
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In this work, a simple, rapid and efficient method for the preparation of benzimidazoles and quinoxalines from the condensation of o-phenylene diamines with aldehydes and/or 1,2-dicarbonyl compounds in the presence of sulfonated rice husk ash (RHA-SO3H) as an efficient green catalyst is reported. RHA-SO3H can be easily prepared using a readily available organic compound by simple modification of rice husk ash. All reactions are performed under mild reaction conditions with high to excellent yields. The method is applicable to aromatic, unsaturated and hetero aromatic aldehydes. The advantages of this method are short reaction times, milder conditions, easy work-up, solvent-free conditions and catalyst reusability.
- Shamsi-Sani, Mahnaz,Shirini, Farhad,Abedini, Masoumeh,Seddighi, Mohadeseh
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p. 1091 - 1099
(2016/04/26)
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- Fe3O4@SiO2@polyionene/Br3- core-shell-shell magnetic nanoparticles: A novel catalyst for the synthesis of imidazole derivatives under solvent-free conditions
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New Fe3O4@SiO2@polyionene/Br3- core-shell-shell magnetite nanoparticles were prepared using a co-precipitation method and were used in the syntheses of imidazole derivatives under solvent-free conditions. The polyionene was easily prepared by reacting DABCO and 1,4-dibromo butane in DMF/methanol. It was then added to the previously formed layers and magnetic core-shell nanoparticles (P-MNPs) were functionalized. All the resultant nanoparticles were characterized by transmission electron microscopy (TEM), scanning electron microscopy (SEM), infrared spectroscopy (FTIR), X-ray diffraction (XRD), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), and vibrating sample magnetometry (VSM). The catalyst was readily recovered by simple magnetic decantation and can be recycled several times with no significant loss of catalytic activity.
- Dezfoolinezhad, Elham,Ghodrati, Keivan,Badri, Rashid
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p. 4575 - 4587
(2016/06/09)
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- Ruthenium(II) carbonyl complexes containing pyridoxal thiosemicarbazone and trans-bis(triphenylphosphine/arsine): Synthesis, structure and their recyclable catalysis of nitriles to amides and synthesis of imidazolines
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Pyridoxal N(4)-substituted thisemicarbazone hydrochloride ligands (L1-3) were synthesized and reacted with the ruthenium(II) starting complexes [RuHCl(CO)(EPh3)3] (EP or As). The resulting complexes [Ru(CO)(L1-3)(EPh3)2] (1-6) were characterized by elemental analyses and spectroscopic techniques. The molecular structure of complex 5 was identified by means of single crystal X-ray diffraction analysis. The catalytic activity of the new complexes was evaluated for the selective hydration of nitriles to primary amides and also the condensation of nitriles with ethylenediamine under solvent free conditions. The processes were operative with aromatic, heteroaromatic and aliphatic nitriles, and tolerated several substitutional groups. The studies on the effect of substitution over thiosemicarbazone, reaction time, temperature, solvent and catalyst loading were carried out in order to find the best catalyst in this series of complexes and favourable reaction conditions. A probable mechanism for both the catalytic reactions of nitrile has also been proposed. The catalyst was recovered and recycled in the hydration of nitriles for five times without any significant loss of its activity.
- Manikandan, Rajendran,Anitha, Panneerselvam,Prakash, Govindan,Vijayan, Paranthaman,Viswanathamurthi, Periasamy,Butcher, Ray Jay,Malecki, Jan Grzegorz
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p. 312 - 324
(2015/01/30)
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- Efficient synthesis of 2-imidazolines in the presence of molecular iodine under ultrasound irradiation
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An efficient one-pot synthesis process for preparing 2-imidazolines from aldehydes and ethylenediamine using molecular iodine and potassium carbonate in absolute ethanol at 25-30°C under ultrasound irradiation is described. The synthetic strategy has the following advantages: mild conditions and low costs requirements, readily available catalyst, short reaction times, simplicity of operation, and good-to-excellent yields.
- Chen, Guo-Feng,Li, Hong-Yang,Xiao, Nan,Chen, Bao-Hua,Song, Ya-Li,Li, Ji-Tai,Li, Zhi-Wei
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p. 1516 - 1521
(2014/12/11)
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- Semi-empirical computation on mechanism of imidazolines and benzimidazoles synthesis and their QSAR studies
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A green, mild and anaerobic synthesis of imidazolines and benzimidazoles from aldehydes and diamines using I2/KI/K2CO3/H2O system has been investigated by semi-empirical methods. The observed efficient direction of the above synthesis has been modeled from a comparison of the energies of four possible transition states arising from mono and di additions of iodines in the configured molecules. In the reaction I1 B is the most favorable transition state [TS] which is shown to be 20 Kcal/mol by PM3 analyses. The resulting trends of relative transition states energies are in excellent agreement with the experimental observations. Also, the bond order, bond length, heat of formation is in good agreement to the formation of product B. In order to establish the suitable mechanism of the reaction a quantitative structure activity relationship analysis has been made using hydrophobicity as the molecular descriptor. In this analysis the values of refractivity, polarizability, hydration energy, electron affinity, ionization potential and dipole moment of the compounds have been correlated with their hydrophobicity which has been taken as the molecular property.
- Hazarika, Swapnali,Konwar, Dilip,Bora, Manas Jyoti
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p. 5073 - 5078
(2015/01/09)
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- COMPOUNDS FOR TREATMENT OF CANCER
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The present invention relates to pharmaceutical compositions for treating cancer comprising BRAF inhibitors, (e.g. vemurafenib) and/or MEK inhibitor, (e.g. trametinib, RO5068760), in combination with anti-tubulin compounds of the invention or other known tubulin inhibitors, and using such compositions for treating cancer such as melanoma, drug-resistant cancer, and cancer metastasis.
- -
-
Paragraph 00220; 00246
(2014/09/29)
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- Microwave mediated solvent free synthesis of 2-arylimidazolines from aldehydes using a solid base catalyst
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2-Aryl imidazolines have been synthesized in solvent free condition using a catalytic amount of solid base (500mg) and by exposure to microwave. Ketones are not affected under these reaction conditions. Reaction time is short, clean products have been obtained and recovery is simple. The yields of the products are good.
- Das, Pranab J.,Baruah, Akashi
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experimental part
p. 752 - 755
(2012/06/30)
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- A facile and efficient synthesis of 2-imidazolines from aldehydes using hydrogen peroxide and substoichiometric sodium iodide
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The reaction of aldehydes with ethylenediamine for the preparation of 2-imidazolines has been studied using hydrogen peroxide as an oxidant in the presence of sodium iodide and anhydrous magnesium sulfate. A mild, green, and efficient method is established to carry out this reaction in high yield. Georg Thieme Verlag Stuttgart · New York.
- Bai, Guo-Yi,Xu, Kai,Chen, Guo-Feng,Yang, Yong-Hui,Li, Tian-Yu
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experimental part
p. 1599 - 1603
(2011/06/25)
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- COMPOUNDS FOR TREATMENT OF CANCER
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The present invention relates to novel compounds having anti-cancer activity, methods of making these compounds, and their use for treating cancer and drug-resistant tumors, e.g. melanoma, metastatic melanoma, drug resistant melanoma, prostate cancer and drug resistant prostate cancer.
- -
-
Paragraph 0040; 00353
(2011/10/03)
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- Dissecting alkynes: Full cleavage of polarized C≡C moiety via sequential bis-michael addition/retro-mannich cascade
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The reaction of diaryl ketoalkynes with 1,2-diamino ethane leads to the full scission of the triple bond with the formation of acetophenone and imidazoline fragments. In this transformation, one of the alkyne carbons undergoes formal reduction with the formation of three C-H bonds, whereas the other carbon undergoes formal oxidation via the formation of three C-N bonds (one π and two σ). Computational analysis confirmed that the key fragmentation step proceeds via a six-membered TS in a concerted manner. Both amines are involved in the fragmentation: the N-H moiety of one amine transfers a proton to the developing negative charge at the enolate oxygen, while the other amine provides direct stereoelectronic assistance to the C-C bond cleavage via a hyperconjugative nN → σ*C-C interaction.
- Roy, Saumya,Davydova, Maria P.,Pal, Runa,Gilmore, Kerry,Tolstikov, Genrikh A.,Vasilevsky, Sergei F.,Alabugin, Igor V.
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experimental part
p. 7482 - 7490
(2011/11/30)
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- New transformation of α-acetylenic ketones under the action of 1,2-diaminoethane
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A reaction of 3-aryl-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-ones with 1,2-diaminoethane in boiling dioxane leads to 2-aryl-4,5-dihydro-1H-imidazoles and 1-(3,4,5-trimethoxy-phenyl)ethanone.
- Davydova,Vasilevskii,Tolstikov
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experimental part
p. 188 - 190
(2011/08/21)
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- Efficient and one-pot catalytic synthesis of 2-imidazolines and bis-imidazolines with p-toluenesulfonic acid under solvent free conditions
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A practical, efficient, and inexpensive method for the synthesis of 2-imidazoline from the reaction of nitriles with ethylenediamine or 1,2-propanediamine using p-toluenesulfonic acid or pyridinium p-toluenesulfonate under reflux conditions is reported. This catalyst can be successfully applied for the chemoselective conversion of dicyanobenzenes to corresponding mono- and bis-imidazolines. The applications of these catalysts are feasible because of easy preparation, easy handling, stability, inexpensive, good activity, and eco-friendly.
- Nasr-Esfahani, Masoud,Montazerozohori, Morteza,Mehrizi, Safie
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experimental part
p. 249 - 254
(2011/05/07)
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- Discovery of novel 2-aryl-4-benzoyl-imidazoles targeting the colchicines binding site in tubulin as potential anticancer agents
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A series of 2-aryl-4-benzoyl-imidazoles (ABI) was synthesized as a result of structural modifications based on the previous set of 2-aryl-imidazole-4- carboxylic amide (AICA) derivatives and 4-substituted methoxylbenzoyl-aryl- thiazoles (SMART). The average IC50 of the most active compound (5da) was 15.7 nM. ABI analogues have substantially improved aqueous solubility (48.9 μg/mL for 5ga vs 0.909 μg/mL for SMART-1, 0.137 μg/mL for paclitaxel, and 1.04 μg/mL for combretastatin A4). Mechanism of action studies indicate that the anticancer activity of ABI analogues is through inhibition of tubulin polymerization by interacting with the colchicine binding site. Unlike paclitaxel and colchicine, the ABI compounds were equally potent against multidrug resistant cancer cells and the sensitive parental melanoma cancer cells. In vivo results indicated that 5cb was more effective than DTIC in inhibiting melanoma xenograph tumor growth. Our results suggest that the novel ABI compounds may be developed to effectively treat drug-resistant tumors.
- Chen, Jianjun,Wang, Zhao,Li, Chien-Ming,Lu, Yan,Vaddady, Pavan K.,Meibohm, Bernd,Dalton, James T.,Miller, Duane D.,Li, Wei
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experimental part
p. 7414 - 7427
(2011/02/23)
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- Efficient catalytic synthesis of 2-imidazolines and bis-imidazolines with silica supported tungstosilicic acid
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A rapid and efficient preparation of 2-imidazolines and bis-imidazolines by the reaction of ethylenediamine or 1,2-propanediamine with nitriles in the presence of catalytic amounts of tungstosilicic acid supported on SiO 2 under reflux condition, is reported. The advantages of this procedure are moderate reaction times, good to high yields and the ability to carry out the large scale reactions. ARKAT USA, Inc.
- Nasr-Esfahani, Masoud,Montazerozohori, Morteza,Moghadam, Majid,Akhlaghia, Parisa
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experimental part
p. 97 - 109
(2010/08/04)
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- Ultrasound promoted synthesis of 2-imidazolines in water: A greener approach toward monoamine oxidase inhibitors
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A series of sixteen 2-substituted-2-imidazolines (where the substituent R = Ph, Me-4-Ph; MeO-4-Ph; (MeO)2-3,4-Ph; (MeO)3-3,4,5-Ph; Ph-4-O-C(O)-Ph; Cl-4-Ph; Cl-2-Ph; Cl2-2,4-Ph; NO2-4-Ph; NO2-3-Ph; Naphth-2-yl; Fur-2-yl; Benzofur-2-yl; Pyridin-2-yl; Quinolin-2-yl) has been synthesized from the reaction of the substituted-aldehydes and ethylenediamine by ultrasound irradiation with NBS in an aqueous medium in high yields (80-99%). The 2-imidazoline ability to inhibit the activity of the A and B isoforms of monoamine oxidase (MAO) was investigated and some of them showed potent and selective MAO inhibitory activity especially for the MAO-B isoform and could become promising candidates for future development.
- Sant' Anna, Gabriela da S.,Machado, Pablo,Sauzem, Patricia D.,Rosa, Fernanda A.,Rubin, Maribel A.,Ferreira, Juliano,Bonacorso, Helio G.,Zanatta, Nilo,Martins, Marcos A.P.
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experimental part
p. 546 - 549
(2011/03/19)
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- Direct oxidative conversion of aldehydes and alcohols to 2-imidazolines and 2-oxazolines using molecular iodine
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Aldehydes were converted to the corresponding 2-imidazolines and 2-oxazolines in good yields by the reaction with ethylenediamine and aminoethanol, respectively, using molecular iodine and potassium carbonate. Moreover, primary alcohols were directly converted to the corresponding 2-imidazolines and 2-oxazolines via aldehydes in one-pot manner with ethylenediamine and aminoethanol, respectively, using molecular iodine and potassium carbonate.
- Ishihara, Midori,Togo, Hideo
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p. 1474 - 1480
(2007/10/03)
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- Facile preparation of 2-imidazolines from aldehydes with tert-butyl hypochlorite
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An efficient and high-yield preparation of 2-imidazolines was achieved from aldehydes and ethylenediamines in the presence of tert-butyl hypochlorite. By this method, 1,3-bis(imidazolin-2-yl)benzene and 2,6-bis(imidazolin-2-yl) pyridine, which act as chiral ligands, could be prepared directly from the corresponding dialdehydes in high yields. Georg Thieme Verlag Stuttgart.
- Ishihara, Midori,Togo, Hideo
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p. 1939 - 1942
(2008/02/10)
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- A convenient synthesis of oxazolines and imidazolines from aromatic aldehydes with pyridinium hydrobromide perbromide in water
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Various 2-oxazolines were prepared from aromatic aldehydes and 2-aminoethanol with pyridinium hydrobromide perbromide in water at room temperature. 2-Imidazolines were also obtained in good yields from aromatic aldehydes and ethylenediamine under the same reaction conditions. Georg Thieme Verlag Stuttgart.
- Sayama, Shinsei
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p. 1479 - 1484
(2007/10/03)
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- An efficient and one-pot synthesis of imidazolines and benzimidazoles via anaerobic oxidation of carbon-nitrogen bonds in water
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The system, I2/KI/K2CO3/H2O, oxidizes carbon-nitrogen bonds for the synthesis of imidazolines and benzimidazoles from aldehydes and diamines under anaerobic conditions in water at 90°C with excellent yields. The process is green, mild and inexpensive.
- Gogoi, Pranjal,Konwar, Dilip
-
-
- An efficient preparation of 2-imidazolines and imidazoles from aldehydes with molecular iodine and (diacetoxyiodo)benzene
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2-Imidazolines were easily prepared in quite good yields from the reaction of aldehydes and ethylenediamine with molecular iodine in the presence of potassium carbonate. Moreover, 2-imidazolines obtained were smoothly oxidized to the corresponding imidazoles in good yields using (diacetoxyiodo)benzene at room temperature. Georg Thieme Verlag Stuttgart.
- Ishihara, Midori,Togo, Hideo
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p. 227 - 230
(2007/10/03)
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- Reactions of 2,3-diaryl-1-methyl-4,5-dihydroimidazolium iodides with nucleophilic reagents
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2,3-Diaryl imidazolium salts, represented by 1 and 2, reacted with 2-ethanolamine or ethylenediamine to produce 2-aryl oxazolines or imidazolines 5-8 respectively. Their hydrolysis resulted in ring-opened ethylenediamine derivatives 9 and 10. The reduction of 1 and 2 produced partially reduced imidazolidines 11, 12 and 11 reacted further with tryptamine to provide 2,3,4,9-tetrahydro-1-phenyl 1H-pyrido[3,4-b]indole, 13. In all these reactions one-carbon units were successfully transferred to the nucleophilic acceptors, which mimic the one-carbon unit transfer function for tetrahydrofolate coenzymes.
- Xia, Chizhong,Hao, Junsheng,Tang, Yiqing,Ni, Yanping,Zhou, Peiwen
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p. 1457 - 1464
(2007/10/03)
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- Synthesis of aldehydes from carboxylic acids via 2-imidazolines
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The use of readily available 2-substituted-2-imidazolines as precursors to 2-hydroxy aldehyde, unsaturated aldehyde and a variety of functionalized aldehydes is reported. It provides a novel method for the preparation of aldehydes from carboxylic acids via 2-substituted-2-imidazolines.
- Shi, Zhen,Gu, Huan
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p. 2701 - 2707
(2007/10/03)
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- N-Nitroso Compounds. Part 1. Structure and Decomposition of N-Nitroso-2-arylimidazolines in Aqueous Acidic Media
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Kinetic measurements for the acid-catalysed decomposition of N-nitroso-2-arylimidazolines are reported.Reactions are first-order in both +>.Two products are formed; an oxazoline, which is the product of hydrolysis of the amidine moiety, and the parent imidazoline formed by denitrosation of the substrate.These products arise from two competing pathways both of which are acid catalysed.The solvent isotope effects for the denitrosation, and amidine hydrolysis, , are 3.1 and 3.5, respectively.The denitrosation pathway, but not amidine hydrolysis, is catalysed by nucleophilic anions, and a value of 1.7 for the Swain-Scott constant, s, is obtained.In the abscence of nucleophilic anions, amidine hydrolysis is preferred over denitrosation, being twice as large as at 25 deg C.Substituents in the 2-aryl ring affect the rate of decomposition giving Hammett ρ values of 0.7 for denitrosation and 1.0 for amidine hydrolysis, which reflect the proximity of the reacting centres to the substituents.Values of the activation parameters are ΔH*NO 74 kJ/mol, ΔH*A 74 kJ/mol, ΔS*NO -48 J/K*mol and ΔS*A -43 J/K*mol.The data are interpreted in terms of a fast equilibrium protonation of the substrate, followed by competitive attack at the protonated substrate, either of water or nucleophilic anions at the nitroso nitrogen atom, or of water at the amidine carbon atom.Protonation is required to activate the substrate, the substrate being recovered from neutral or alkaline solutions unchanged.The mechanism is discussed with reference to the analogous reactions of N-nitrosoamines and N-nitrosoamides.
- Iley, Jim,Norberto, Fatima,Rosa, Eduarda
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p. 1471 - 1476
(2007/10/02)
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