- Copper-catalyzed ring-opening reactions of alkyl aziridines with b2 pin2: Experimental and computational studies
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The possibility to form new C–B bonds with aziridines using diboron derivatives con-tinues to be a particularly challenging field in view of the direct preparation of functionalized β-aminoboronates, which are important compounds in drug discovery, being a bioisostere of β-aminoacids. We now report experimental and computational data that allows the individua-tion of the structural requisites and of reaction conditions necessary to open alkyl aziridines using bis(pinacolate)diboron (B2 pin2 ) in a regioselective nucleophilic addition reaction under copper catalysis.
- Boldrini, Cosimo,Comparini, Lucrezia Margherita,Di Bussolo, Valeria,Di Pietro, Sebastiano,Favero, Lucilla,Menichetti, Andrea,Pineschi, Mauro
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supporting information
(2021/12/17)
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- Supported benzimidazole-salen Cu(II) complex: An efficient, versatile and highly reusable nanocatalyst for one-pot synthesis of hybrid molecules
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A novel and efficient nanocatalyst consisting of benzimidazole-salen Cu(II) complex on surface-modified silica (BS-Cu(II)@SiO2) was prepared. The heterogeneous nanocatalyst was characterized by FESEM, TEM, EDX, FT-IR, XRD, ICP, and TGA. The nanocatalyst was used for the one-pot synthesis of some target hybrid molecules. An efficient four component C–H bond activation/[3?+?2] cycloaddition and condensation/cyclization/aromatization sequence toward triazole-benzimidazole derivatives is disclosed. This methodology provides a general and rapid synthetic route to some new triazole-benzimidazole hybrids under mild reaction conditions. In addition, the heterogeneous nanocatalyst can be easily separated from the reaction mixture and used several times without noticeable leaching or loss of its catalytic activity. We believe this interesting one-pot reaction as well as benzimidazole-salen Cu(II) complex pave the way to the design and synthesis of other new hybrid molecules and metal catalysts, respectively.
- Sharghi, Hashem,Aberi, Mahdi,Shiri, Pezhman
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- Catalytic transformation of esters of 1,2-azido alcohols into α-amido ketones
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The esters of 1,2-azido alcohols were transformed into α-amido ketones without external oxidants through the Ru-catalyzed formation of N-H imines with the liberation of N2 followed by intramolecular migration of the acyl moiety. A wide range of α-amido ketones were obtained, and one-pot transformation into the corresponding oxazoles (or a thiazole) was demonstrated.
- Kim, Yongjin,Pak, Han Kyu,Rhee, Young Ho,Park, Jaiwook
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supporting information
p. 6549 - 6552
(2016/06/01)
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- Design, synthesis and biological evaluation of novel 1,2,3-triazolyl β -hydroxy alkyl/carbazole hybrid molecules
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The design, synthesis and biological study of several novel 1,2,3-triazolyl β -hydroxy alkyl/carbazole hybrid molecules as a new type of antifungal agent has been described. In this synthesis, the N-alkylation reaction of carbazol-9-ide potassium salt with 3-bromoprop-1-yne afforded 9-(prop-2-ynyl)-9H-carbazole. The ‘Click’ Huisgen cycloaddition reaction of 9-(prop-2-ynyl)-9H-carbazole with diverse β -azido alcohols in the presence of copper-doped silica cuprous sulphate led to target molecules in excellent yields. The in vitro antifungal and antibacterial activities of title compounds were screened against various pathogenic fungal strains, Gram-positive and/or Gram-negative bacteria. In particular, 1-(4-((9H-carbazol-9-yl) methyl)-1H-1,2,3-triazol-1-yl)-3-butoxypropan-2-ol (10e) proved to have potent antifungal activity against all fungal tests compared with fluconazole and clotrimazole as studied reference drugs. Our molecular docking analysis revealed an appropriate fitting and a potential powerful interaction between compound 10e and an active site of the Mycobacterium P450DM enzyme. The strong hydrogen bondings between β -hydroxyl and ether groups in 10e were found to be the main factors that drive the molecule to fit in the active site of enzyme. The in silico pharmacokinetic studies were used for a better description of 10a–10n as potential lead antifungal agents for future investigations.
- Rad, Mohammad Navid Soltani,Behrouz, Somayeh,Behrouz, Marzieh,Sami, Akram,Mardkhoshnood, Mehdi,Zarenezhad, Ali,Zarenezhad, Elham
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p. 705 - 718
(2016/07/12)
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- Copper/graphene/clay nanohybrid: A highly efficient heterogeneous nanocatalyst for the synthesis of novel 1,2,3-triazolyl carboacyclic nucleosides via 'Click' Huisgen 1,3-dipolar cycloaddition
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A very mild and highly efficient synthesis of some novel 1H-1,2,3-triazolyl carboacyclic nucleosides via a 'Click' Huisgen cycloaddition of N-propargyl nucleobases and azido alcohols using Cu/aminoclay/reduced graphene oxide nanohybrid (Cu/AC/r-GO nanohybrid) as nanocatalyst is described. The preparation and characterization of Cu/AC/r-GO nanohybrid are discussed. This catalyst was characterized by X-ray diffraction, FT-IR, TEM, and energy-dispersive analysis of X-ray techniques. Cu/AC/r-GO nanohybrid is a stable and highly efficient heterogeneous nanocatalyst that can be easily prepared, used, and restored from the reaction mixture by simple filtration, and reused for many consecutive trials without significant decrease in activity.
- Navid Soltani Rad, Mohammad,Behrouz, Somayeh,Jafar Hoseini,Nasrabadi, Hasan,Saberi Zare, Maryam
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p. 1210 - 1224
(2015/09/28)
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- Synthesis of 1,2-azidoalcohols from epoxides using a task-specific protic ionic liquid: 1-hydrogen-3-methylimidazolium azide
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A task-specific ionic liquid as an environmentally eco-friendly green catalyst has been synthesized and used in the ring opening of epoxides under green conditions. In order to use protic ionic liquids (PIL), we decided to synthesize 1,2-azidoalcohols via
- Heidarizadeh, Fariba,Beitsaeed, Ali,Rezaee-Nezhad, Eshagh
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p. 450 - 453
(2014/05/06)
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- One-pot synthesis of tweezer-like calix[4]resorcinarene decorated with pendant heterocyclic moieties: An efficient and recyclable heterogeneous PTC for the preparation of azidohydrins in water
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Direct incorporation of ionic liquid onto the upper rim of calix[4]resorcinarene led to the formation of tweezer-like calix[4]resorcinarene via one-pot strategy. The formation of this cationic supramolecular structure was confirmed by 1H NMR,
- Mouradzadegun, Arash,Elahi, Somayeh,Abadast, Fatemeh
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p. 1636 - 1641,6
(2014/10/15)
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- 'Click synthesis' of some novel o-substituted oximes containing 1,2,3-triazole-1,4-diyl residues as new analogs of β-adrenoceptor antagonists
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The 'click synthesis' of some novel O-substituted oximes, 7a-7t, which contain 1,2,3-triazolediyl residues, as new analogs of β-adrenoceptor antagonists is described (Schemes 1-4). The synthesis of these compounds was achieved in four to five steps. The formation of oximes of 9H-fluoren-9-one and benzophenone, i.e., 9a and 9b, respectively, followed by their reaction with propargyl bromide, afforded O-propargyl oximes 10a and 10b, respectively, which by a subsequent CuI-catalyzed Huisgen cycloaddition with prepared β-azido alcohols 11a-11j (Schemes 2 and 3), led to the target compounds 7a-7t in good yields. Copyright
- Rad, Mohammad Navid Soltani,Behrouz, Somayeh,Karimitabar, Fatemeh,Khalafi-Nezhad, Ali
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experimental part
p. 491 - 501
(2012/05/04)
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- Phosphine-catalyzed heine reaction
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Aziridines are important synthetic intermediates which readily undergo ring-opening reactions. It is demonstrated that electron-rich phosphines are efficient catalysts for the regioselective rearrangement of N-acylaziridines to oxazolines. The reactions o
- Martin, Allen,Casto, Kathleen,Morris, William,Morgan, Jeremy B.
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supporting information; experimental part
p. 5444 - 5447
(2011/12/05)
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- Heteroarylalkyl-8-azabicyclo[3.2.1]octane compounds as mu opioid receptor antagonists
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The invention provides heteroarylene substituted 8-azabicyclo[3.2.1]octane compounds of formula (I): wherein R1, R2, A, and m are defined in the specification, or a pharmaceutically-acceptable salt thereof, that are antagonists at th
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Page/Page column 15
(2009/04/24)
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- Chiral phosphinothiourea organocatalyst in the enantioselective Morita-Baylis-Hillman reactions of aromatic aldehydes with methyl vinyl ketone
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A new class of chiral phosphinothioureas has been developed as efficient organocatalyst for the enantioselective Morita-Baylis-Hillman reaction of aromatic aldehydes with methyl vinyl ketone. The reaction proceeds under very mild conditions to afford the
- Yuan, Kui,Zhang, Lei,Song, Hong-Liang,Hu, Yinjun,Wu, Xin-Yan
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supporting information; experimental part
p. 6262 - 6264
(2009/04/04)
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- Oxidation of azides by the HOF·CH3CN: A novel synthesis of nitro compounds
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The HOF·CH3CN complex, readily prepared by passing F 2 through aqueous acetonitrile, is an exceptionally efficient oxygen transfer agent. It is unique in its capacity to oxidize various azides into the corresponding nitro derivatives. This method requires short reactions times and room temperature or below, and the desired nitro compounds were usually isolated in very good yields. The respective nitroso derivatives are believed to be the intermediates in this reaction. Functional groups such as aromatic rings, ketones, nitriles, halides, alcohols, and esters are tolerated. Sulfides react with HOF·CH3CN usually at the same rate as azides. Amines and olefins, however, react faster, so they have to be protected first. Nitro derivatives with various oxygen isotopes can be made using the labeled H 18OF·CH3CN. In the case of chiral azides the stereochemistry around the nitrogen-bonded carbons is retained.
- Carmeli, Mira,Rozen, Shlomo
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p. 4585 - 4589
(2007/10/03)
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- Transition metal-catalyzed synthesis and reactivity of N-alkenyl aziridines
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(Chemical Equation Presented) Straightforward methods for palladium-catalyzed alkenylation of aziridines with alkenyl halides and copper-catalyzed alkenylation of aziridines with alkenyl boronic acids have been developed. This methodology offers attractive alternatives to the known methods requiring activated alkenyl halides and acetylenes. A wide variety of N-alkenyl aziridines containing substituents other than electron-withdrawing substituants such as cyano groups and sulfones have been synthesized in good yields. Furthermore, these N-alkenyl aziridines exhibit quite a different reactivity from conventional enamines, as demonstrated by their reactivity.
- Dalili, Shadi,Yudin, Andrei K.
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p. 1161 - 1164
(2007/10/03)
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- High yield regioselective ring opening of epoxides using samarium chloride hexahydrate
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Epoxides were converted to the corresponding β-azidohydrins and β-iodohydrins using SmCl3·6H2O/NaN3 in DMF and SmCl3·6H2/NaI in acetonitrile respectively. The reactions were highly regio-selective, ef
- Bhaumik, Kankan,Mali, Umesh W.,Akamanchi
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p. 1603 - 1610
(2007/10/03)
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- N-arylation of aziridines
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A range of N-arylaziridines were prepared by the palladium or copper catalyzed amination reaction between N-H aziridines and aryl bromides or arylboronic acids. These results showcase the synthetic utility of metal-bound aziridine species in nitrogen tran
- Sasaki, Mikio,Dalili, Shadi,Yudin, Andrei K.
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p. 2045 - 2047
(2007/10/03)
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- One step synthesis of 1,2,3-triazole carboxylic acids
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Disclosed is a one step method for preparing a 1,2,3-triazole carboxylic acid by treating an azide with a β-ketoester in the presence of a base.
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- Base-promoted elaboration of aziridines
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The base-promoted isomerization of aziridines to allyl amines is still an almost unknown reaction. However, the use of superbasic reagents has shown to be able to promote a regio- and stereoselective conversion of monocyclic and bicyclic sulfonyl aziridin
- Mordini, Alessandro,Russo, Francesco,Valacchi, Michela,Zani, Lorenzo,Degl'Innocenti, Alessandro,Reginato, Gianna
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p. 7153 - 7163
(2007/10/03)
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- IL-8 RECEPTOR ANTAGONISTS
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This invention relates to the use of phenyl ureas of formulas (I) and (II) in the treatment of disease states mediated by the chemokine, Interleukin-8 (IL-8). The variables of (I) and (II) are defined herein. STR1
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- Regioselective azidolysis of epoxides catalyzed with Ce(IV)
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Regioselective conversion of epoxides to 1,2-azidoalcohols was performed efficiently with sodium azide in t-butanol and in the presence of catalytic amounts of Ce(IV) as ceric ammonium nitrate (CAN).
- Iranpoor, Nasser,Kazemi, Foad
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p. 561 - 566
(2007/10/03)
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- A one step conversion of olefins into α-azidoketones using azidotrimethylsilane-chromium trioxide reagent system
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α-Azidoketones are conveniently obtained in good yields from the corresponding olefins upon reaction with azidotrimethylsilane-chromium trioxide reagent system.
- Venkat Ram Reddy,Kumareswaran,Vankar, Yashwant D.
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p. 6751 - 6754
(2007/10/02)
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