- FLEXIBLE PIEZOELECTRIC AND FERROELECTRIC HALOIMIDAZOLE CRYSTALS
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Provided herein are substituted haloimidazole crystals, the substituted haloimidazole crystal comprising a substituted haloimidazole compound wherein the substituents are selected from the group consisting of hydrogen, an alkyl, and a halogen. The substituted haloimidazole crystals may further comprise second substituted haloimidazole. The substituted haloimidazole crystals may be piezoelectric, ferroelectric, flexible, or any combination thereof. Also provided herein are methods for preparing substituted haloimidazole crystals.
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Paragraph 0076
(2019/05/15)
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- New approach to electrochemical iodination of arenes exemplified by the synthesis of 4-iodopyrazoles of different structures
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The two-stage electrosynthesis of 4-iodosubstituted pyrazole derivatives was performed. At the first stage, KIO3 was obtained at the Ni anode under the undivided galvanostatic conditions of electrolysis of an aqueous alkaline solution of KI (or I2) at the Ni anode. At the second stage, pyrazole and its derivatives were iodinated in the heterophase (H2O-CHCl3 (CCl4)) medium by the KIO3-KI (or KIO3-I2) system in the presence of H2SO4. The yields of iodopyrazoles were 74-92%. The electrochemical iodination of anisole, 2-methylpyrazole, and thiophene was carried out to form 4-iodoanisole (88% yield), 4,5-diiodo-2-methylimidazole (54% yield), and a mixture of 2-iodothiophene (60% yield) and 2,5-diiodothiophene (4% yield).
- Lyalin,Petrosyan
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p. 360 - 367
(2015/02/05)
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- Synthesis, crystal structure and antibacterial activity of new highly functionalized ionic compounds based on the imidazole nucleus
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Several new highly functionalized imidazolium derivatives were synthesized, via appropriate synthetic routes, using imidazole, 1-methylimidazole and 2-phenyl-1-methylimidazole as key intermediates. The antibacterial activity of the prepared compounds was evaluated against: Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa and Salmonella thipymurium using disk-diffusion and MIC methods. Crystal X-ray structures are reported for six compounds.
- Bahnous, Mebarek,Bouraiou, Abdelmalek,Chelghoum, Meryem,Bouacida, Sofiane,Roisnel, Thierry,Smati, Farida,Bentchouala, Chafia,Gros, Philippe C.,Belfaitah, Ali
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p. 1274 - 1278
(2013/03/14)
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- Ionic liquid iodinating reagent for mild and efficient iodination of aromatic and heteroaromatic amines and terminal alkynes
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Hexamethylene bis(N-methylimidazolium) bis(dichloroiodate) (HMBMIBDCI), an ionic liquid iodinating reagent, have been prepared and characterized. Its ability to perform iodination reactions with a variety of substrates has been explored. In general, iodination reactions of aromatic and heteroaromatic amines proceed with good yields in the absence of solvent. Reactions of terminal alkynes in the presence of 1,8-diazabicyclo [5.4.O] undec-7-ene and tetrahydrofuran have been investigated as well.
- Nouzarian, Mahboobe,Hosseinzadeh, Rahman,Golchoubian, Hamid
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supporting information
p. 2913 - 2925
(2013/09/02)
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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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- A simple method for iodination of heterocyclic compounds using HIO 4/NaCl/silica gel/H2SO4 in water
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A fast and simple method for iodination of some heterocycles is reported. The reactions were carried out in water, using HIO4/H 2SO4/NaCl/silica gel at moderate temperatures of 25-50 °C. Springer-Verlag 2011.
- Hosseini, Abolfazl,Khalilzadeh, Mohammad A.,Hosseinzadeh, Masoumeh,Tajbakhsh, Mahmoud
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experimental part
p. 619 - 623
(2012/07/14)
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- 5,6,7,8-TETRAHYDRO-IMIDAZO[1,5-A]PYRAZINE COMPOUNDS
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The invention relates to 5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine derivatives of formula (I) wherein R1, R2, R3, and R4 are as described n the description, to salts, especially pharmaceutically acceptable salts thereof, and to the use of such compounds as medicaments; especially as orexin receptor antagonists.
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Page/Page column 21
(2011/05/08)
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- Direct synthesis of pyrroles via a silver-promoted three-component reaction involving unusual imidazole ring opening
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A novel silver-promoted three-component reaction toward the synthesis of multifunctionalized pyrroles has been developed. This reaction involves an unusual imidazole ring decomposition, presumably via 1,5-isomerization and subsequent hydrolysis.
- Zeng, Jing,Bai, Yaguang,Cai, Shuting,Ma, Jimei,Liu, Xue-Wei
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supporting information; experimental part
p. 12855 - 12857
(2012/02/03)
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- Pyrrolopyrazine Kinase Inhibitors
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The present invention relates to the use of novel pyrrolopyrazine derivatives of Formula I, wherein the variables n, p, q, Q, X, X′ and Y are defined as described herein, which inhibit JAK and SYK and are useful for the treatment of auto-immune and inflammatory diseases.
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Page/Page column 109
(2011/10/10)
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- Discovery of MK-5046, a potent, selective bombesin receptor subtype-3 agonist for the treatment of obesity
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We report the development and characterization of compound 22 (MK-5046), a potent, selective small molecule agonist of BRS-3 (bombesin receptor subtype-3). In pharmacological testing using diet-induced obese mice, compound 22 caused mechanism-based, dose-
- Sebhat, Iyassu K.,Franklin, Christopher,Lo, Michael M.-C.,Chen, David,Jewell, James P.,Miller, Randy,Pang, Jianmei,Palyha, Oksana,Kan, Yanqing,Kelly, Theresa M.,Guan, Xiao-Ming,Marsh, Donald J.,Kosinski, Jennifer A.,Metzger, Joseph M.,Lyons, Kathryn,Dragovic, Jasminka,Guzzo, Peter R.,Henderson, Alan J.,Reitman, Marc L.,Nargund, Ravi P.,Wyvratt, Matthew J.,Lin, Linus S.
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supporting information; experimental part
p. 43 - 47
(2011/04/17)
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- A new, mild one-pot synthesis of iodinated heterocycles as suitable precursors for N-heterocyclic carbene complexes
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The use of I2/AgOAc in dichloromethane constitutes a cheap, mild, and efficient method for the selective iodination of a variety of heterocycles. In a number of cases, this method provides superior yields to other literature methods and affords iodo-functionalized heterocycles that are suitable precursors for carbene complexes.
- Iglesias, Manuel,Schuster, Oliver,Albrecht, Martin
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experimental part
p. 5423 - 5425
(2010/11/02)
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- Substituted inmidazoles as bombesin receptor subtype-3 modulators
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Certain novel substituted imidazoles are ligands of the human bombesin receptor and, in particular, are selective ligands of the human bombesin receptor subtype-3 (BRS-3). They are therefore useful for the treatment, control, or prevention of diseases and disorders responsive to the modulation of BRS-3, such as obesity, and diabetes.
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Page/Page column 27
(2010/02/17)
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- 5,6,7,8-TETRAHYDRO-IMIDAZO[1,5-A]PYRAZINE COMPOUNDS
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The invention relates to 5,6,7,8-tetrahydro-imidazo[1,5- a]pyrazine derivatives of formula (I) wherein R1, R2, R3, and R4 are as described n the description, to salts, especially pharmaceutically acceptable salts thereof, and to the use of such compounds as medicaments; especially as orexin receptor antagonists.
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Page/Page column 47
(2010/01/30)
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- 5,6,7,8-TETRAHYDRO-IMIDAZO[1,5-A]PYRAZINE DERIVATIVES
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The invention relates to 5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine derivatives of formula (I),wherein X represents CH2 or O; R1 represents a phenyl group, which group is independently mono-, di-, or tri-substituted wherein the substituents are independently selected from the group consisting of (C1-4)alkyl, (C1-4)alkoxy, halogen, cyano, trifluoromethoxy and trifluoromethyl; R2 represents (C1-4)alkyl, (C1-4)alkoxy, (C2-4)alkenyl, halogen, cyano, hydroxymethyl, trifluoromethyl, C(O)NR5R6 or cyclopropyl; R3 represents (C1-4)alkyl, (C1-4)alkoxy-methyl or halogen; R4 represents (C1-4)alkyl; R5 represents hydrogen or (C1-4)alkyl; and R6 represents hydrogen or (C1-4)alkyl. The invention also relates to pharmaceutically acceptable salts of such compounds; and to the use of such compounds as medicaments; especially as orexin receptor antagonists.
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Page/Page column 62
(2008/12/06)
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- Aromatic iodination in aqueous solution. A new lease of life for aqueous potassium dichloroiodate
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A re-investigation of the use of aqueous potassium dichloroiodate (KICl2) as an iodinating agent for aromatic compounds has found the reagent to be more generally applicable than previously known. The reagent has been found to give excellent yields of iodinated heterocyclic compounds, such as isatin, imidazole and pyrazole.
- Garden, Simon J.,Torres, José C.,De Souza Melo, Simone C.,Lima, Alexandre S.,Pinto, Angelo C.,Lima, Edson L.S.
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p. 2089 - 2092
(2007/10/03)
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- Preparation of new magnesiated functionalized imidazoles and antipyrines via an iodine-magnesium exchange
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The iodine-magnesium exchange using i-PrMgBr allows the preparation of magnesiated 3-pyrazolin-5-ones (antipyrines) and functionalized imidazoles which after reaction with various electrophiles afford polyfunctional 5- membered heterocycles.
- Dehmel, Florian,Abarbri, Mohamed,Knochel, Paul
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p. 345 - 346
(2007/10/03)
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- A Pd-catalyzed double coupling reaction to 4,5-disubstituted imidazole alkynes
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A palladium-catalyzed double coupling reaction of 4,5-diiodoimidazoles 2, which were prepared by diiodination of imidazole, and terminal alkynes provided the corresponding imidazole diynes 3.
- Kim,Kang,Ryu,Keum,Seo
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p. 507 - 512
(2007/10/03)
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- Synthesis of 4,4'-biimidazoles
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The palladium(0) catalysed coupling reaction of 4-iodo-1-triphenylmethylimidazole (7) or its 2-methyl analogue 8 afforded the 4,4'-biimidazoles 9 and 10, respectively. Treatment of these compounds with 60% aqueous trifluoroacetic acid gave 4,4'-biimidazole and 2,2'-dimethyl-4,4'-biimidazole as their bistrifluoroacetate salts 11 and 12, respectively.
- Cliff,Pyne
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p. 681 - 682
(2007/10/02)
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- 2(1H)-Quinolinones with Cardiac Stimulant Activity. 3. Synthesis and Biological Properties of 6-Imidazol-1-yl Derivatives
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A series of 6-imidazol-1-yl-8-methyl-2(1H)-quinolinones was synthesized and evaluated for cardiac stimulant activity in dogs.The majority of compounds were prepared from an appropriate 6-imidazol-1-yl-2(1H)-quinolinone precursor or by sulfuric acid cataly
- Bell, Andrew S.,Campbell, Simon F.,Morris, David S.,Roberts, David A.,Stefaniak, Mark H.
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p. 1552 - 1558
(2007/10/02)
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- Quinolone cardiac stimulants
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A quinolone cardiac stimulant of the formula:- or a pharmaceutically acceptable salt thereof,wherein R, which is attached to the 5-, 7- or 8-position of the quinolone, is H or C1-C4 alkyl;, R1 is a group of the formula -S(O)n/s
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- 6-heteroaryl quinolone inotropic agents
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A series of novel heterocyclic-substituted 2-(1H)-quinolone compounds have been prepared, including the 3,4-dihydro derivatives thereof, wherein the heterocyclic ring moiety is a pyrrolyl, imidazolyl, pyrazolyl, triazolyl or tetrazolyl group attached by a nitrogen atom of said group to the 5-, 6-, 7- or 8-positions of the quinolone ring. These particular compounds are useful in therapy as highly potent inotropic agents and therefore, are of value in the treatment of various cardiac conditions. Preferred member compounds include 6-(2,4-dimethylimidazol-1-yl)-8-methyl-2-(1H)-quinolone, 6-(2,4-dimethyl-5-nitroimadazol-1-yl)-8-methyl-2-(1H)-quinolone, 8-methyl-6-(tetrazol-1-yl)-2-(1H)-quinolone, 8-methyl-6-(1,2,4-triazol-4-yl)-2-(1H)-quinolone, and 6-(4-cyano-2-methylimidazol-1-yl)-8-methyl-2-(1H)-quinolone, respectively. Methods for preparing these compounds from known starting materials are provided.
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- Methyl substituted imidazol-1-yl quinolones
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A series of novel heterocyclic-substituted 2-(1H)-quinolone compounds have been prepared wherein the heterocyclic ring moiety is a substituted pyrrolyl, imidazolyl, pyrazolyl, triazolyl or tetrazolyl group attached by a nitrogen atom of said group to the
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- Kinetics of Iodination of 4-Methylimidazole and 2-Methylimidazole
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Since the rate law for the diiodination of imidazole provides information on the iodination of C4(5) but not C2 in the imidazole ring, we have investigated the kinetics of iodination of the two positions separately in 2-methylimidazole and 4-methylimidazole, respectively.The observed rate laws for the methylimidazoles exhibited hydrogen ion dependencies that differed from that of imidazole; the iodinations of all three substrates were base catalyzed, but like imidazole, 2-methylimidazole undergoes uncatalyzed iodination, while 4-methylimidazole does not.The overall rate of iodination of 4-methylimidazole was faster than that of 2-methylimidazole which was faster than that of imidazole.
- Vaughan, John D.,Vaughan, Virginia L.,Daly, Steven S.,Smith, William A.
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p. 3108 - 3111
(2007/10/02)
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