26818-07-5Relevant articles and documents
Oxymetallation. Part 14. Modified Procedures for t-Butyl Peroxymercuriation and Bromodemercuriation that Lead to an Improved, Stereoselective, Conversion of Non-terminal Alkenes into β-Bromoalkyl
Bloodworth, A. J.,Courtneidge, J. L.
, p. 3258 - 3264 (1981)
Stereospecific trans-peroxymercuriation of non-terminal alkenes with little or no accompanying acyloxymercuriation has been accomplished by using mercury(II) acetate under conditions of equilibrium control induced by the presence of 20 molpercent of perch
Synthesis of new 1,4- and 1,5-disubstituted N-ethyl acetate and N-α-butyro-γ-lactone alkylimidazole derivatives as N-acylhomoserine lactone analogs
Zhang, Qiang,Li, Si-Zhe,Queneau, Yves,Soulère, Laurent
, p. 2298 - 2303 (2021/09/16)
New alkylimidazoles functionalized with a homoserine lactone or an alkyloxycarbonyl moiety have been synthesized as N-acylhomoserine lactones (AHLs) analogs. The 1,4-disubstituted imidazole derivatives were prepared by alkylation of 4(5)-alkylimidazoles with α-bromo-γ-butyrolactone or ethyl α-bromoacetate. An alternative route was preferred for the synthesis of their 1,5-disubstituted counterparts based on the use of a N1-protected alkylimidazole, its alkylation to an N3-imidazolyl-α-acetate and deprotection to the desired 1,5-disubstituted esters and subsequent alkylation of the acetate moiety with cyclic ethylene sulfate followed by acid-catalyzed cyclization. The ability to modulate bacterial quorum sensing of all new compounds was compared to that of previously reported AHL analogs in which the amide bond is replaced by a heterocyclic group.
Using Small-Molecule Adjuvants to Repurpose Azithromycin for Use against Pseudomonas aeruginosa
Hubble, Veronica B.,Hubbard, Brittany A.,Minrovic, Bradley M.,Melander, Roberta J.,Melander, Christian
, p. 141 - 151 (2019/01/04)
A major contributor to fatalities in cystic fibrosis (CF) patients stems from infection with opportunistic bacterium Pseudomonas aeruginosa. As a result of the CF patient's vulnerability to bacterial infections, one of the main treatment focuses is antibiotic therapy. However, the highly adaptive nature of P. aeruginosa, in addition to the intrinsic resistance to many antibiotics exhibited by most Gram-negative bacteria, means that multi-drug-resistant (MDR) strains are increasingly prevalent. This makes the eradication of pseudomonal lung infections nearly impossible once the infection becomes chronic. New methods to treat pseudomonal infections are greatly needed in order to eradicate MDR bacteria found within the respiratory tract, and ultimately better the quality of life for CF patients. Herein, we describe a novel approach to combatting pseudomonal infections through the use of bis-2-aminoimidazole adjuvants that can potentiate the activity of a macrolide antibiotic commonly prescribed to CF patients as an anti-inflammatory agent. Our lead bis-2-AI exhibits a 1024-fold reduction in the minimum inhibitory concentration of azithromycin in vitro and displays activity in a Galleria mellonella model of infection.
Synthesis of various cyclopropyl methyl bromide and its derivatives from ketones and/or aldehydes and some β-dicarbonyl compounds in the presence of BrCN and Et3N
Gholizadeh, Saeed,Safa, Kazem D.,Noroozi Pesyan, Nader
, p. 1239 - 1253 (2019/04/27)
The ultimate goal in this paper has been developed for the synthesis of structurally various bromomethyl cyclopropane via an α-bromoketone and/or aldehydes with ethyl cyanoacetate or malononitrile and cyanogen bromide (BrCN) in the presence of Et3N to give products in excellent yields within about 3?s. All structures were characterized by IR, 1H-NMR, 13C-NMR, and Mass spectroscopy techniques. The reaction mechanism was discussed.
NOVEL 5-SUBSTITUTED IMIDAZOLYLMETHYL DERIVATIVES
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Page/Page column 96, (2018/04/17)
The present invention relates to novel 5-substituted imidazolylmethyl derivatives, to processes for preparing these compounds, to compositions and mixtures comprising these compounds, and to the use thereof as biologically active compounds, especially for
Metal-free protocol for the synthesis of α-bromo ketones from olefins using TsNBr2
Rajbongshi, Kamal Krishna,Hazarika, Debojit,Phukan, Prodeep
supporting information, p. 356 - 358 (2015/04/27)
TsNBr2 reacts readily with olefins to produce α-bromo ketones at room temperature. The synthesis was carried out by treating an olefin with TsNBr2 in acetone-water mixture in 30:1 ratio. Excellent yield of corresponding α-bromo ketone could be achieved within a short time.
Coplanar bithiazole-centered heterocyclic aromatic fluorescent compounds having different donor/acceptor terminal groups
Tao, Tao,Peng, Yu-Xin,Huang, Wei,You, Xiao-Zeng
, p. 2472 - 2481 (2013/05/22)
A family of stable and soluble bithiazole-centered heterocyclic aromatic fluorescent compounds is described herein. All these multiple N-donor containing compounds have effective π-conjugated systems and different imidazole, pyridine, thiophene, triphenyl
Direct conversion of olefins into α-bromo ketones using O-iodoxybenzoic acid and tetraethylammonium bromide
Deshmukh, Swapnil S.,Chaudhari, Kiran H.,Akamanchi, Krishnacharya G.
experimental part, p. 81 - 83 (2011/03/20)
Utilizing full potential of IBX, a mild, selective, and facile method has been developed for the direct conversion of olefins into the corresponding α-bromo ketones by using 1.1 equivalents each of o-iodoxybenzoic acid and tetraethylammonium bromide. Georg Thieme Verlag Stuttgart - New York.
Fast oxidation of secondary alcohols by the bromate-bromide system using cyclic microwave heating in acidic water
P??kk?nen, Sanna,Pursiainen, Jouni,Lajunen, Marja
scheme or table, p. 6695 - 6699 (2011/02/23)
We report an improved, gentle, cyclic microwave activation technique for the oxidation of secondary alcohols using nonhazardous hypobromous acid (BrOH) as the reagent in acidic water. Several aliphatic and aromatic secondary alcohols were successfully oxidized to the corresponding ketones using this technique in high yields and with only minor amounts of side products.
Facile one-pot synthesis of α-bromoketones from olefins using bromide/bromate couple as a nonhazardous brominating agent
Patil, Rajendra D.,Joshi, Girdhar,Adimurthy, Subbarayappa,Ranu, Brindaban C.
experimental part, p. 2529 - 2532 (2009/09/06)
A new method for the preparation of α-bromoketones from olefins using bromide/bromate couple as a nonhazardous brominating agent has been developed. Several α-bromoketones were successfully prepared from a variety of olefins by this method. This procedure is an alternative to conventional molecular bromine.
