- Photophysical properties and photoreduction of N-acetyl- and N-benzoylphthalimides
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The photophysical properties and photoreduction of N-acetylphthalimide (AcP) and N-benzoylphthalimide (BzP), N-3,4,5-trimethoxybenzoylphthalimide (trimethoxyBzP) and N-4-nitrobenzoylphthalimide (nitroBzP) were studied by steady-state and transient techniques. Radicals and their precursor triplet states were detected by flash photolysis. The triplet state properties of AcP and BzP were characterized. In contrast, no triplet absorption was observed with ns-detection for trimethoxyBzP and nitroBzP. Specific products are formed upon electron transfer from triethylamine to the photoexcited acylphthalimides. In addition, H-atom transfer from 2-propanol or other alcohols to the triplet state takes place. The properties of several radical intermediates involved in photoreduction of the acylphthalimides as well as some structure-function relationships are described.
- Biczók, László,G?rner, Helmut
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- Single-pot tandem oxidative/C-H modification amidation process using ultrasmall PdNP-encapsulated porous organosilica nanotubes
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Herein, we studied a single-pot method with a dual catalysis process towards the conversion of primary aromatic alcohols to amides using ultrasmall PdNPs of controlled uniform size (1.8 nm) inside hybrid mesoporous organosilica nanotubes (MO-NTs). The cat
- Gholipour, Behnam,Liu, Xiao,Rostamnia, Sadegh,Zonouzi, Afsaneh
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p. 4276 - 4287
(2022/02/16)
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- Nano-construction of CuO nanorods decorated with g-C3N4 nanosheets (CuO/g-C3N4-NS) as a superb colloidal nanocatalyst for liquid phase C[sbnd]H conversion of aldehydes to amides
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Herein, we describe an intelligent strategy to fabricate nanosheets of graphitic carbon nitride (g-C3N4) decorated with nanorods copper oxide (CuO NRs). Then, the catalytic activity of CuONRs/g-C3N4-NS was developed for the synthesis of primary amides in water. The morphology of CuO and its synergetics effect with nanosheets g-C3N4 a major role in the yield of products. Furthermore, hydroxylamine hydrochloride (NH2OH·HCl) due to availability and affordability was used as a suitable substitute for ammonia source. The findings demonstrate that this layer nanostructure is a superb catalyst for converting various derivatives of aldehyde to their corresponding amides. The current protocol can be useful criterion in the synthesis and stabilization of metal oxides and provides new insight in organic transformation.
- Mohammadi, Robabeh,Gholipour, Behnam,Alamgholiloo, Hassan,Rostamnia, Sadegh,Mohtasham, Hamed,Zonouzi, Afsaneh,Ramakrishna, Seeram,Shokouhimehr, Mohammadreza
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- Chemoselective Synthesis of Aryl Ketones from Amides and Grignard Reagents via C(O)-N Bond Cleavage under Catalyst-Free Conditions
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Conversion of a wide range of N-Boc amides to aryl ketones was achieved with Grignard reagents via chemoselective C(O)-N bond cleavage. The reactions proceeded under catalyst-free conditions with different aryl, alkyl, and alkynyl Grignard reagents. α-Ketoamide was successfully converted to aryl diketones, while α,β-unsaturated amide underwent 1,4-addition followed by C(O)-N bond cleavage to provide diaryl propiophenones. N-Boc amides displayed higher reactivity than Weinreb amides with Grignard reagents. A broad substrate scope, excellent yields, and quick conversion are important features of this methodology.
- Sureshbabu, Popuri,Azeez, Sadaf,Muniyappan, Nalluchamy,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
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p. 11823 - 11838
(2019/10/02)
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- Base promoted peroxide systems for the efficient synthesis of nitroarenes and benzamides
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A useful and efficient approach for the synthesis of nitroarenes from several aromatic amines (including heterocycles) using peroxide and base has been developed. This oxidative reaction is very easy to handle and afforded the products in good yields. Formation of benzamides from benzylamine was also successfully carried out with this metal-free catalytic system in good to excellent yields.
- Gupta, Sampa,Ansari, Alisha,Sashidhara, Koneni V.
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supporting information
(2019/09/07)
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- Uniformly dispersed copper nanoparticles onto the modified magnetically recoverable nanocatalyst for aqueous synthesis of primary amides
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Magnetically recoverable and environmentally friendly Cu-based heterogeneous catalyst has been synthesized for the one-pot conversion of aldehydes to their corresponding primary amides. The Fe3O4@SiO2 nanocomposites were prepared by synthesis of Fe3O4 magnetic nanoparticles (MNPs) which was then coated with a silica shell via St?ber method. Bi-functional cysteine amino acid was covalently bonded onto the siliceous shell of nanocatalyst. The CuII ions were then loaded onto the modified surface of nanocatalyst. Finally, uniformly dispersed copper nanoparticles were achieved by reduction of CuII ions with NaBH4. Amidation reaction of aryl halides with electron-withdrawing or electron-donating groups and hydroxylamine hydrochloride catalyzed with Fe3O4@SiO2@Cysteine-copper (FSC-Cu) MNPs in aqueous condition gave an excellent yield of products. The FSC-Cu MNPs could be easily isolated from the reaction mixture with an external magnet and reused at least 8 times without significant loss in activity.
- Ziaee, Fariborz,Gholizadeh, Mostafa,Seyedi, Seyed Mohammad
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- Metal-Free Thermal Activation of Molecular Oxygen Enabled Direct α-CH2-Oxygenation of Free Amines
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Direct oxidation of α-CH2 group of free amines is hard to achieve due to the higher reactivity of amine moiety. Therefore, oxidation of amines involves the use of sophisticated metallic reagents/catalyst in the presence or absence of hazardous oxidants under sensitive reaction conditions. A novel method for direct C-H oxygenation of aliphatic amines through a metal-free activation of molecular oxygen has been developed. Both activated and unactivated free amines were oxygenated efficiently to provide a wide variety of amides (primary, secondary) and lactams under operationally simple conditions without the aid of metallic reagents and toxic oxidants. The method has been applied to the synthesis of highly functionalized amide-containing medicinal drugs, such as O-Me-alibendol and -buclosamide.
- Ghosh, Santanu,Jana, Chandan K.
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p. 260 - 266
(2018/02/19)
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- A selective hydration of nitriles catalysed by a Pd(OAc)2-based system in water
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In situ formation of a [Pd(OAc)2bipy] (bipy = 2,2′-bipyridyl) complex in water selectively catalyses the hydration of a wide range of organonitriles at 70 °C. Catalyst loadings of 5 mol% afford primary amide products in excellent yields in the absence of hydration-promoting additives such as oximes and hydroxylamines.
- Sanz Sharley, Daniel D.,Williams, Jonathan M.J.
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supporting information
p. 4090 - 4093
(2017/09/27)
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- Exfoliation effect of PEG-type surfactant on Pd supported GO (SE-Pd(nanoparticle)/GO) in cascade synthesis of amides: A comparison with Pd(nanoparticle)/rGO
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In the presence investigation, a cascade method for the synthesis of primary amides is discussed by the catalysis of Pd supported onto graphene oxide (Pd/GO) nanosheets. Also, the effect of different polyethyleneglycol-type (PEG-type) polyethers including PEG-300, P123 and F127 on the catalytic activity of Pd/rGO is studied in the the reaction of aldehyde and hydroxylamine hydrochloride to give benzamide. Addition of PEG-type polyethers played an important role in raising the catalytic power of Pd(nanoparticle)/GO by exfoliation of GO sheets. The present paper introduces Pd(nanoparticle)/GO as first Pd supported GO for the synthesis of primary amides through this method. This catalyst was highly active, efficient, tolerant, and environmentally benign in one-pot conditions with recyclability at least for 8 runs. Also, this study suggests the prevailing catalytic activity of Pd(nanoparticle)/GO rather to Pd(nanoparticle)/rGO in a comparitive experiment.
- Rostamnia, Sadegh,Doustkhah, Esmail,Zeynizadeh, Behzad
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- Copper nanoparticles on charcoal: An effective nanocatalyst for the synthesis of enol carbamates and amides via an oxidative coupling route
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The catalytic activity of copper nanoparticles on charcoal (Cu/C) was investigated as an environmentally friendly heterogeneous catalyst for the synthesis of enol carbamates and amides via the oxidative coupling of N,N-dialkyl formamides with 1,3-dicarbonyl compounds and aromatic aldehydes with amine hydrochloride salts, respectively. Various enol carbamates and amides were synthesized in moderate to good yields using this method. Moreover, the catalyst could be recovered and subsequently reused in further reactions.
- Saberi, Dariush,Mansoori, Sakineh,Ghaderi, Esmali,Niknam, Khodabakhsh
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supporting information
p. 95 - 99
(2015/12/23)
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- Copper(II) acetate-catalysed conversion of aldoximes to amides under mild conditions
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A mild method for the metal-catalysed conversion of aldoximes to amides has been achieved by the combined use of copper(II) acetate and MeCN in EtOH under reflux. The presence of a catalytic amount of MeCN (0.05 equiv.) accelerated the reaction and improved the yield. Aryl, heteroaryl and alkyl aldoximes were transformed into the corresponding amides in moderate to good yield. 2-Furyl and 2-Thiophenyl aldoximes, which possess a heteroatom lone pair positioned ortho to the oximido group, showed enhanced reactivity, and the corresponding amides were obtained in excellent yield.
- Ma, Xiaoyun,Lu, Ming
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p. 594 - 596
(2016/10/21)
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- Impact of Functional Groups on the Copper-Initiated N-Arylation of 5-Functionalized Pyrrolidin-2-ones and Their Vinylogues
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The electronic effects governing the N-arylation of pyrrolidone were investigated. The generalization of our preliminary findings on a copper(I)-catalyzed Csp2-N coupling process was first improved with a wide variety of aryl and heteroaryl halides and methyl pyroglutamate. The optimized protocol was further extended to pyrrolidin-2-ones substituted at the C5-position with an aryl group bearing an electron-donating or electron-withdrawing group as well as to some of their substituted enaminoester vinylogues. The impact of substituents at the N- and C5-position on these coupling processes seemed to be pivotal for determining both the reaction profiles and yields.
- Baudelet, Davy,Da?ch, Adam,Rigo, Beno?t,Lipka, Emmanuelle,Gautret, Philippe,Homerin, Germain,Claverie, Christelle,Rousseau, Jolanta,Abuhaie, Cristina-Maria,Ghinet, Alina
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p. 2226 - 2244
(2016/07/15)
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- Visible Light-Induced Iodine-Catalyzed Transformation of Terminal Alkynes to Primary Amides via C≡C Bond Cleavage under Aqueous Conditions
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The visible light-induced iodine-catalyzed oxidative cleavage of the C≡C bond for transforming terminal alkynes into primary amides in the presence of ammonia under aqueous conditions is described. This metal-free protocol which ensued via initial hydroamination of the acetylene bond followed by liberation of diiodomethane (CH2I2) was found to be applicable to aromatic, heteroaromatic and aliphatic alkynes.
- Dighe, Shashikant U.,Batra, Sanjay
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supporting information
p. 500 - 505
(2016/02/12)
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- Efficient and selective copper-grafted nanoporous silica in aqueous conversion of aldehydes to amides
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The one-pot conversion of aldehydes to their corresponding primary amides has been studied using SBA-15-grafted ethylenediamine copper complexes (En-Cu). The heterogeneous catalyst could be readily isolated from the reaction mixture and reused at least 14 times without significant loss in activity. The influence of reaction parameters was studied and the conditions determining yields and selectivities, including quantity of catalyst, solvent and base, were optimized to afford amides in high yields. The structures of synthesized catalysts were investigated using different characterization techniques including Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), CHN, atomic absorption (AA), scanning electron microscopy (SEM) and transmission electron microscopy (TEM).
- Rostamnia, Sadegh,Nouruzi, Nasrin,Xin, Hongchuan,Luque, Rafael
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p. 199 - 205
(2015/02/02)
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- Copper-catalyzed aerobic oxidative C-C bond cleavage for C-N bond formation: From ketones to amides
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A novel copper-catalyzed aerobic oxidative C(CO)-C(alkyl) bond cleavage reaction of aryl alkyl ketones for C-N bond formation is described. A series of acetophenone derivatives as well as more challenging aryl ketones with long-chain alkyl substituents could be selectively cleaved and converted into the corresponding amides, which are frequently found in biologically active compounds and pharmaceuticals.
- Tang, Conghui,Jiao, Ning
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supporting information
p. 6528 - 6532
(2014/06/24)
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- Molecular iodine-mediated domino reaction for the synthesis of benzamides, 2,2-Diazidobenzofuran-3(2H)-ones and benzoxazolones
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A simple and efficient domino protocol has been developed for the preparation of biologically important benzamides, 2,2-diazidobenzofuran-3(2H)- ones and benzoxazolones from various structurally and electronically divergent acetophenones and ortho-hydroxyacetophenones in the presence of molecular iodine, sodium azide and sodium bicarbonate at 100 °C in good to excellent yields. Copyright
- Rajendar,Kant, Ruchir,Narender
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supporting information
p. 3591 - 3596
(2014/01/06)
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- A mild and expeditious synthesis of amides from aldehydes using bio glycerol-based carbon as a recyclable catalyst
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The new bioglycerol-based carbon catalyst acts as an efficient, readily available, and reusable catalyst for the synthesis of amides, when aldehyde and hydroxylamine hydrochloride react in acetonitrile.
- Ramesh,Narayana Murthy,Karnakar,Harsha Vardhan Reddy,Nageswar,Vijay,Prabhavathi Devi,Prasad
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supporting information; experimental part
p. 2636 - 2638
(2012/06/30)
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- Highly efficient one-pot synthesis of primary amides catalyzed by scandium(III) triflate under controlled MW
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The present Letter highlights a versatile synthetic protocol for the one-pot synthesis of primary amides employing scandium(III) triflate as a catalyst in water under controlled MW. This methodology offers excellent yields in shorter reaction times with enhanced selectivity.
- Allam, Bharat Kumar,Singh, Krishna Nand
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experimental part
p. 5851 - 5854
(2011/12/03)
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- Metal-free one-pot oxidative conversion of benzylic alcohols and benzylic halides into aromatic amides with molecular iodine in aq ammonia, and hydrogen peroxide
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Various primary alcohols, particularly benzylic alcohols, could be converted into the corresponding aromatic amides in good yields in a one-pot manner by treatment with molecular iodine in aq. NH3, followed by reaction with ~30% aq H2O2. Similarly, various benzylic halides could be also converted into the corresponding aromatic amides in good yields in a one-pot manner by treatment with molecular iodine in aq NH3, followed by reaction with ~30% aq H2O 2. The present reactions involve the metal-free one-pot oxidative conversion of benzylic alcohols and benzylic halides into the corresponding aromatic amides, respectively.
- Ohmura, Ryosuke,Takahata, Misato,Togo, Hideo
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experimental part
p. 4378 - 4381
(2010/09/12)
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- Palladium-catalyzed one-pot conversion of aldehydes to amides
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The palladium-catalyzed one-pot conversion of aldehydes into primary amides in the presence of hydroxylamine hydrochloride in aqueous dimethyl sulfoxide (DMSO) at moderate temperature is described. The process is selective and free from the addition of an external chelating ligand.
- Ali, Md. Ashif,Punniyamurthy, Tharmalingam
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experimental part
p. 288 - 292
(2010/04/28)
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- Convenient removal of N-tert-butyl from amides with scandium triflate
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Scandium triflate has been used as a convenient and efficient catalyst for removal of N-tert-butyl from amide groups. A variety of N-tert-butyl aryl and alkyl amides under these conditions gave the corresponding primary amide in high yields. With the use of microwave heating the deprotection reaction could be completed within 1 h.
- Mahalingam,Wu, Xiongyu,Alterman, Mathias
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p. 3051 - 3053
(2007/10/03)
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- Cytosporone E: Racemic synthesis and preliminary antibacterial testing
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The antibiotic cytosporone E (isolated from the broth of the endophytic fungi CR 200 (Cytospora sp.) and CR 146 (Diaporthe sp.)) was synthesized as a racemic mixture. The key step in the synthesis is the Meyers ortho-alkylation of a chiral aromatic oxazoline. Preliminary antibiotic activity shows antibiosis against Gram-positive bacteria but not Gram-negative bacteria as previously reported.
- Hall, Jeffrey D.,Duncan-Gould, Nathan W.,Siddiqi, Nasar A.,Kelly, Jennifer N.,Hoeferlin, L. Alexis,Morrison, Susan J.,Wyatt, Justin K.
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p. 1409 - 1413
(2007/10/03)
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- SUBSTITUTED 4-(1H-BENZIMIDAZOL-2-YL)[1,4]DIAZEPANES USEFUL FOR THE TREATMENT ALLERGIC DISEASES
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The present invention relates to novel 4-(1H-benzimidazol-2-yl)[1,4] diazepane derivatives of formula (1): and stereoisomers thereof, and pharmaceutically acceptable salts thereof which are useful as histamine receptor antagonists and tachykinin receptor antagonist. Such antagonists are useful in the treatment of allergic rhinitis, including seasonal rhinitis and sinusitis; inflammatory bowel diseases, including Crohn's disease and ulcerative colitis; asthma; bronchitis; and emesis.
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- NOVEL HETEROCYCLIC SUBSTITUTED PYRROLIDINE AMIDE DERIVATIVES
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The present invention relates to novel heterocyclic substituted pyrrolidine amide derivatives of formula (1), and stereoisomers and pharmaceutically acceptable salts thereof and their use as tachykinin receptor antagonists. Such antagonists are useful in the treatment of tachykinin-mediated diseases and conditions disclosed herein including: asthma, cough, and bronchitis.
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- Novel substituted 4-(1H-benzimidazol-2-yl) [1,4]diazepanes useful for the treatment of allergic diseases
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The present invention relates to novel 4-(1H-benzimidazol-2-yl)[1,4]diazepane derivatives of formula and stereoisomers thereof, and pharmaceutically acceptable salts thereof which are useful as histamine receptor antagonists and tachykinin receptor antagonist. Such antagonists are useful in the treatment of allergic rhinitis, including seasonal rhinitis and sinusitis; inflammatory bowel diseases, including Crohn's disease and ulcerative colitis; asthma; bronchitis; and emesis.
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- Substituted 4-(1H-benzimidazol-2-yl)[1,4]diazepanes useful for the treatment of allergic disease
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The present invention relates to novel 4-(1H-benzimidazol-2-yl)[1,4]diazepane derivatives of formula (1): and stereoisomers thereof, and pharmaceutically acceptable salts thereof which are useful as histamine receptor antagonists and tachykinin receptor antagonist. Such antagonists are useful in the treatment of allergic rhinitis, including seasonal rhinitis and sinusitis; inflammatory bowel diseases, including Crohn's disease and ulcerative colitis; asthma; bronchitis; and emesis.
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- Substituted 4-(1H-benzimidazol-2-yl-amino)piperidines useful for the treatment of allergic diseases
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The present invention relates to novel substituted piperidine derivatives of formula (1), stereoisomers thereof, and pharmaceutically acceptable salts thereof which are useful as histamine receptor antagonists and tachykinin receptor antagonist. Such antagonists are useful in the treatment of allergic rhinitis, including seasonal rhinitis and sinusitis; inflammatory bowel diseases, including Crohn's disease and ulcerative colitis; asthma; bronchitis; and emesis.
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- CARBOXYSUBSTITUTED CYCLIC CARBOXAMIDE DERIVATIVES
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The present invention relates to novel carboxy substituted cyclic carboxamide derivatives of formula (1), STR1 and stereoisomers and pharmaceutically acceptable salts thereof and their use as tachykinin receptor antagonists. Such antagonists are useful in the treatment of tachykinin-mediated diseases and conditions disclosed herein including: asthma, coughs and bronchitis.
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- Stability and degradation kinetics of 5'-deoxy-5-fluoro-N4-(3,4,5-trimethoxybenzoyl)cytidine in aqueous solution
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The stability of 5'-deoxy-5-fluoro-N4-(3,4,5-trimethoxybenzoyl)cytidine (Ro 09-1390) in buffered solutions at 37 °C was studied. Seven degradation products were identified by high-performance liquid chromatography (HPLC) and spectroscopy. The degradation products were different depending on the pH of the solution. Ro 09-1390 was unstable at pH 2.1 and stable at around pH 5.6 in spite of forming several decomposition products; and its degradation rate did not change in the pH range from 8 to 12. The degradation of Ro 09-1390 followed apparent first order kinetics and the decomposition pathway at alkaline conditions was different from the one at acidic conditions. On the other hand, at neutral pH the other decomposition products were formed.
- Nakai,Sasai,Ezawa
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p. 2568 - 2571
(2007/10/02)
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- New Syntheses of 3-Indolylglyoxal
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In a study of the possibilities of a simple method for the preparation of 3-indolylglyoxals two new methods for the synthesis of indolylglyoxal structures were proposed.The first method consists in oxidation of 3-hydroxyacetylindole with the dimethyl sulfoxide - oxalyl chloride complex, but for a number of reasons it is virtually inapplicable to the preparation of substituted indolylglyoxals.In the second case the readily synthesized 3-indolylglyoxyl chlorides are reduced to the corresponding aldehydes in good yields by means of trialkyltin hydrides.
- Vereshchagin, A. L.,Bryanskii, O. V.,Semenov, A. A.
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- Studies on SRN1 Reactions. Part 6: Synthesis of 3-Methyl Derivatives of the Alkaloids Thalactamine, Doryanine, and 6,7-Dimethoxy-N-methyl-1(2H)-isoquinolone
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A new, short synthesis of the 3-methyl derivatives (3a-c) of the alkaloids thalactamine, doryanine, and 6,7-dimethoxy-N-methyl-1(2H)-isoquinolone, based upon our previous SRN1 synthesis of isocarbostryril systems, is reported.
- Beugelmans, Rene,Ginsburg, Helene,Bois-Choussy, Michele
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p. 1149 - 1152
(2007/10/02)
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