3600-18-8Relevant academic research and scientific papers
Lipophilic indole mediated chemoselective α-monobromination of 1,3-dicarbonyl compounds
Wong, Jonathan,Ke, Zhihai,Yeung, Ying-Yeung
, (2020/03/04)
A mild and efficient mono-selective bromination of 1,3-dicarbonyl compounds has been developed using lipophilic indole catalysts. Inexpensive and commercially available N-bromosuccinimide (NBS) was used as the brominating reagent. The selectivity was further enhanced when using stoichiometric amount of 3-bromoindole species. Mechanistic studies reveal that the indole catalyst has dual functions in the mono-bromination process.
Oxidative [3+3] Annulation of Atropaldehyde Acetals with 1,3-Bisnucleophiles: An Efficient Method of Constructing Six-Membered Aromatic Rings, Including Salicylates and Carbazoles
Gu, Yanlong,Wu, Fengtian,Yang, Jian
, p. 2727 - 2741 (2018/07/29)
An oxidative [3+3] annulation of atropaldehyde acetals with various 1,3-bisnucleophiles was developed using either N-bromosuccinimide or copper(II) bromide as oxidizing reagent and Br?nsted or Lewis acids as catalyst. The [3+3] annulations can be considered mechanistically as oxidizing reagent-induced acid-acid-catalyzed domino reactions established through the concept of auto-tandem catalysis. Alkyl acetoacetates, α-(indol-2-yl)acetate, anilines, 1-methyl-1H-pyrazol-3-amine, ethyl 5-amino-1H-pyrazole-3-carboxylate, and 3-amino-1H-indazole can all be used as 1,3-bisnucleophiles in this type of transformation. The established reactions can very efficiently construct six-membered aromatic rings, including salicylates and carbazoles. A four-step method of synthesizing the anti-inflammatory agent diflunisal was also developed based on the oxidative [3+3] annulation reaction, and the yield was high. (Figure presented.).
NBS mediated protocol for the synthesis of N-bridged fused heterocycles in water
Bhagat, Saket B.,Telvekar, Vikas N.
supporting information, p. 3662 - 3666 (2017/08/23)
A facile and environmental friendly protocol for the synthesis of N-bridged fused bicyclic compounds such as imidazo[1,2-a]pyridines, imidazo[1,2-a]pyrimidines, and imidazo[2,1-b]thiazole, from commercially available starting materials has been developed.
Novel Metal- and Mineral-Acid-Free Synthesis of Organic Ammonium Tribromides and Application of Ethylenephenanthrolium Bistribromide for Bromination of Active Methylene Group of 1,3-Diketones and β-Ketoesters
Dey, Rupa Rani,Paul, Bappi,Dhar, Siddhartha Sankar
supporting information, p. 724 - 736 (2015/10/29)
A novel procedure for the preparation of organic ammonium tribromides (OATBs) is described from their corresponding bromides. Quaternary ammonium bromides (QABs) and a N,N′-heterocyclic dibromide are efficiently oxidized to their corresponding monotribromides and bistribromide by m-chloroperbenzoic acid (MCPBA) in the presence of 2 and 4 equiv of KBr, respectively. The reactions are carried out in an aqueous medium without the use of any mineral acid or metal catalyst/promoters. A variety of tribromides are synthesized in very good yields including a hitherto unknown reagent, 1,10-(ethane-1, 2-diyl)phenanthrolinediium bistribromide (EPDBT). EPDBT is investigated as brominating agent and found to be highly effective for selective bromination of active methylene groups of a variety of 1,3-diketones and β-ketoesters. GRAPHICAL ABSTRACT.
Synthesis and antimicrobial activities of a series of 2,5-substituent 1,4-cyclohexanedione derivatives
Liu, Hui-Lian,Wang, Qing-Zhong,Guo, Shu-Hua
, p. 1349 - 1352 (2013/05/09)
A series of 2,5-substituent 1,4-cyclohexanedione derivatives compounds were designed and synthesized. Their structures were identified by elemental analysis, 1H NMR, IR spectra. Their assayed antibacterial (Escherichia coli, Bacillus subtilis) and antifungal (Candida albicans) activities were also evaluated by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) method. The results of biological test showed 2,5-dibenzylformate 1,4-cyclohexanedione (11) and 2,5-diformanilide 1,4-cyclohexanedione (12) have favorable antimicrobial activity with MICs of 26.7, 33.6, 24.2 and 32.3 μg/mL against Escherichia coli and Bacillus subtilis, respectively. Copyright
Substituted imidazo[1,2- a ]pyridines as β-strand peptidomimetics
Kang, Chang Won,Sun, Yongmao,Del Valle, Juan R.
supporting information, p. 6162 - 6165 (2013/04/10)
New conformationally extended dipeptide surrogates based on an imidazo[1,2-a]pyridine scaffold are described. Efficient synthesis and incorporation into host peptides affords structures with native side-chain functionality and hydrogen bonding elements on
Facile and efficient method for oc-monobromination of dicarbonyl compounds with N-bromosuccinimide
Fang, Li-Zhen,Shen, Jiu-Ming,Lv, Qing-Hua,Yan, Fu-Lin
experimental part, p. 3425 - 3427 (2012/02/04)
The a-monobrominated products were prepared fast in presence of p-TsOH as catalyst in very high yields using various 1,3-diketones and β-keto-esters with N-bromosuccinimide in CH2C12.
Design, synthesis, and biological evaluation of antiviral agents targeting flavivirus envelope proteins
Li, Ze,Khaliq, Mansoora,Zhou, Zhigang,Post, Carol Beth,Kuhn, Richard J.,Cushman, Mark
experimental part, p. 4660 - 4671 (2009/07/11)
Flavivirus envelope proteins (E proteins) have been shown to play a pivotal role in virus assembly, morphogenesis, and infection of host cells. Inhibition of flavivirus infection of a host cell by means of a small molecule envelope protein antagonist is an attractive strategy for the development of antiviral agents. Virtual screening of the NCI chemical database using the dengue virus envelope protein structure revealed several hypothetical hit compounds. Bioassay results identified a class of thiazole compounds with antiviral potency in cell-based assays. Modification of these lead compounds led to a series of analogues with improved antiviral activity and decreased cytotoxicity. The most active compounds 11 and 36 were effective in the low micromolar concentration range in a cellular assay system.
α-bromination of 1,3-dicarbonyl compounds using Dess-Martin periodinane (DMP) and tetraethylammonium bromide (TEAB)
Salgaonkar, Paresh D.,Shukla, Vidyanand G.,Akamanchi, Krishnacharya G.
, p. 275 - 280 (2007/10/03)
A mild and expeditious method for α-bromination of 1,3-dicarbonyl compounds using Dess-Martin periodinane and tetraethylammonium bromide is described. Copyright Taylor & Francis Group, LLC.
Halogenation of carbonyl compounds by an ionic liquid, [AcMIm]X, and Ceric Ammonium Nitrate (CAN)
Ranu, Brindaban C.,Adak, Laksmikanta,Banerjee, Subhash
, p. 358 - 362 (2008/02/13)
An ionic liquid, acetylmethylimidazolium halide ([AcMIm]X), in combination with ceric ammonium nitrate promotes halogenations of a wide variety of ketones and 1,3-keto esters at the ?-position. The ionic liquid acts here as reagent as well as reaction medium, and thus the reaction does not require any organic solvent or conventional halogenating agent. The reaction is completely arrested when the radical quencher TEMPO is used. A plausible radical mechanism is also suggested. CSIRO 2007.
