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Karel Škoch, Ivana Císařová, Filip Uhlík, Petr Štěpnička
Isomeric phosphinoferrocene ligands, viz. 1'-(diphenylphosphino)-1-cyanoferrocene (1) and 1'-(diphenylphosphino)-1-isocyanoferrocene (2), show markedly different coordination behaviours. For instance, the reactions of 1 with [PdCl2(MeCN)2] and [(LNC)Pd(μ-Cl)]2 (LNC = [2-(dimethylamino-κN)methyl]phenyl-κC1) produced the "phosphine" complexes [PdCl2(1-κP)2] (7) and [(LNC)PdCl(1-κP)] (8), and the latter was converted into the coordination polymer [(LNC)Pd(μ(P,N)-1)][SbF6] (9). Conversely, the reaction of 2 with [(LNC)Pd(μ-Cl)]2 involved coordination of the phosphine moiety and simultaneous insertion of the isocyanide group into the Pd-C bond, giving rise to the P,η1-imidoyl complex [PdCl(Ph2PfcN[double bond, length as m-dash]CC6H4CH2NMe2-κ3C,N,P)] (10; fc = ferrocene-1,1'-diyl)...
October 10, 2018: Dalton Transactions: An International Journal of Inorganic Chemistry
Maryam Khalesi, Azim Ziyaei Halimehjani, Max Franz, Marc Schmidtmann, Jürgen Martens
Consecutive multicomponent reactions have been applied for the synthesis of novel pseudo-peptides bearing dithiocarbamate and N,X-heterocyclic groups (X = S, O) in only one structure. The first multicomponent reaction includes the synthesis of dithiocarbamates using an amine or amino acid, CS2 and an electrophile. The second MCR is synthesis of Asinger imines using 2-chloroisobutyraldehyde, NaXH (X = S, O), ketone and ammonia. The final MCR is Ugi reaction to afford the corresponding three-dimensional pseudo-peptides...
October 4, 2018: Amino Acids
Shu Hu, Bi-Ju Liu, Jia-Min Feng, Cheng Zong, Kai-Qiang Lin, Xiang Wang, De-Yin Wu, Bin Ren
Precise measurement of the temperature right at the surface of thermoplasmonic nanoparticles is a grand challenge but extremely important for the photochemical reaction and photothermal therapy. We present here a method capable of measuring the surface temperature of plasmonic nanostructures with surface-enhanced Raman spectroscopy (SERS), which is not achievable by existing methods. We observe a sensitive shift of stretching vibration of phenyl isocyanide (PIC) molecule with temperature (0.232 cm-1/ºC) as a result of the temperature-dependent molecular orientation change...
October 3, 2018: Journal of the American Chemical Society
Jordy M Saya, Thomas R Roose, Jarryt J Peek, Bram Weijers, Thomas J S de Waal, Christophe M L Vande Velde, Romano V A Orru, Eelco Ruijter
The N-iodosuccinimide-mediated spirocyclization of tryptamine-derived isocyanides to generate spiroindolenines is reported. The products contain both an imine and an imidoyl iodide as flexible handles for follow-up chemistry. Nucleophilic addition typically occurs chemoselectively on the imine moiety with complete diastereoselectivity, providing opportunities for the construction of complex molecular frameworks. The synthetic potential of the method was showcased in the formal total synthesis of (±)-aspidofractinine...
October 1, 2018: Angewandte Chemie
Gabriel Dos Passos Gomes, Yulia Loginova, Sergey Z Vatsadze, Igor V Alabugin
Radical addition to isonitriles (isocyanides) starts and continues all the way to the TS mostly as a simple addition to a polarized π-bond. Only after the TS has been passed, the spin density moves to the α-carbon to form the imidoyl radical, the hallmark intermediate of the 1,1-addition-mediated cascades. Addition of alkyl, aryl, heteroatom-substituted and heteroatom-centered radicals reveals a number of electronic, supramolecular, and conformational effects potentially useful for the practical control of isonitrile-mediated radical cascade transformations...
October 1, 2018: Journal of the American Chemical Society
Julio Fernandez-Cestau, Luca Rocchigiani, Anna Pintus, Raquel J Rama, Peter H M Budzelaar, Manfred Bochmann
Isocyanides insert into gold(iii)-hydrogen bonds to give the first examples of gold iminoformyl complexes. The reaction is initiated by catalytic amounts of radicals; DFT calculations indicate that this is an equilibrium reaction driven forward by isocyanide in sufficient excess to trap the Au(ii) intermediate.
October 9, 2018: Chemical Communications: Chem Comm
Jana Wiemann, Lucie Fischer Née Heller, Jacqueline Kessler, Dieter Ströhl, René Csuk
Isocyanide-based multicomponent reactions - especially the standard four component Ugi reaction - provide an easy and powerful access to compounds with an auspicious pharmacological potential. Therefore, a set of 16 novel derivatives of the diterpene dehydroabietylamine was synthesized by the Ugi-4CR. The subsequent screening of the synthesized α-acylamino carboxamides in colorimetric sulforhodamine B assays revealed an in vitro cytotoxicity towards several human tumor cell lines. Particularly, the rhodamine B conjugates 14-16 showed a remarkable cytotoxic activity, characterized by EC50 values in a low three-digit nanomolar range...
September 11, 2018: Bioorganic Chemistry
Darren James Dixon, Allegra Franchino, Jack Chapman, Ignacio Funes-Ardoiz, Robert Paton
Chiral amines bearing a stereocenter in the α position are ubiquitous compounds with many applications in the pharmaceutical and agrochemical sectors, as well as in catalysis. Catalytic asymmetric Mannich additions represent a valuable method to access such compounds in enantioenriched form. Herein, we report the first enantio- and diastereoselective addition of commercially available p-toluenesulfonylmethyl isocyanide (TosMIC) to ketimines, affording 2-imidazolines bearing two contiguous stereocenters, one of which is fully-substituted, with high yields and excellent stereocontrol...
September 23, 2018: Chemistry: a European Journal
Lisa Moni, Fabio De Moliner, Silvia Garbarino, Jörn Saupe, Christian Mang, Andrea Basso
An Ugi multicomponent reaction with chiral cyclic amino acids, benzyl isocyanide and cyclic ketones (or acetone) has been exploited as key step for the generation of peptidomimetics. After a straightforward set of elaborations, the peptidomimetics were converted into polycyclic scaffolds displaying two orthogonally protected secondary amines. Libraries of compounds were obtained decorating the molecules through acylation/reductive amination reactions on these functional groups.
2018: Frontiers in Chemistry
Nada Y Tashkandi, Sarah L McOnie, Jeremy L Bourque, Crispin R W Reinhold, Kim Marie Baines
The addition of 2,6-dimethylphenyl isocyanide and t-butyl isocyanide to tetramesityldisilene was examined. In both cases, the initially formed product is an iminodisilirane; however, the iminodisiliranes are unstable under the reaction conditions and react with a second equivalent of the isocyanide to give either a 3-silaazetidine or a novel bicyclic double enamine, respectively. Taken together with the previous examples in the literature, the results demonstrate that subtle differences in the steric bulk of the disilene or the electronic effects of the isocyanide can lead to dramatic differences in the reaction pathway...
September 17, 2018: Angewandte Chemie
Tomohiro Seki, Koh Kobayashi, Takaki Mashimo, Hajime Ito
The epistatic double hydrogen bonds that arise from the presence of a pendant carboxy group in a gold isocyanide complex result in strong aurophilic interactions in a magenta-emitting polymorph. This is due to the lack of the typically antiparallel dimer arrangements, which often prevent the formation of strong aurophilic interactions. Furthermore, this polymorph shows hypsochromically shifted luminescence mechanochromism.
October 2, 2018: Chemical Communications: Chem Comm
Wen-Hu Bao, Chao Wu, Jing-Ting Wang, Wen Xia, Ping Chen, Zilong Tang, Xinhua Xu, Wei-Min He
A simple and practical molecular iodine-mediated method for the efficient construction of thiocarbamates from isocyanides, thiols and water under metal-free and mild conditions has been developed. A variety of thiocarbamates were easily synthesized through this methodology, which has the advantages of simple operation, eco-friendly conditions, good functional group tolerance, and readily accessible raw materials.
September 26, 2018: Organic & Biomolecular Chemistry
Jian Zhang, Peiyuan Yu, Shao-Yu Li, He Sun, Shao-Hua Xiang, Jun Joelle Wang, Kendall N Houk, Bin Tan
The Ugi reaction constructs α-acylaminoamide compounds by combining an aldehyde or ketone, an amine, a carboxylic acid, and an isocyanide in a single flask. Its appealing features include inherent atom and step economy together with the potential to generate products of broad structural diversity. However, control of the stereochemistry in this reaction has proven to be a formidable challenge. We describe an efficient enantioselective four-component Ugi reaction catalyzed by a chiral phosphoric acid derivative that delivers more than 80 α-acylaminoamides in good to excellent enantiomeric excess...
September 14, 2018: Science
Manijeh Nematpour, Elham Rezaee, Mehdi Jahani, Sayyed Abbas Tabatabai
A facile sonochemical route for the synthesis of benzo[1,3]thiazine derivatives via a one pot, multicomponent, intramolecular CH activation reaction from isocyanides, aniline and benzoyl (acetyl) isothiocyanate adduct catalyzed by copper (I) iodide in acetone at 30 °C have been reported. The advantages of the described method include using simple and readily available starting materials and performing under mild copper-catalytic reaction conditions and also obtaining pure product with high yield without applying column chromatography...
August 3, 2018: Ultrasonics Sonochemistry
Han-Han Kong, Hong-Ling Pan, Ming-Wu Ding
A new efficient Ag-catalyed cascade cycloisomerization/aerobic oxidation reaction of a Ugi-azide adduct for the preparation of 3-acylpyrroles using molecular oxygen as the terminal oxidant has been developed. A series of 2-tetrazolyl-substituted 3-acylpyrroles were obtained in 62-89% yields from readily available enynals 1, primary amines 2, isocyanides 3, and trimethylsilyl azide 4 in the presence of a catalytic amount of AgNO3 and DMAP under an O2 atmosphere.
September 27, 2018: Journal of Organic Chemistry
Xiaojuan Yu, Hua Hou, Baoshan Wang
Heptafluoroisobutyronitrile (C4) has been utilized as a dielectric compound to replace sulfur hexafluoride for the sake of environmental concern. Energetic profiles of the potential energy surface for the unimolecular reaction of C4 were calculated using density functional theory (M06-2X), quadratic complete basis set (CBS-QB3), Gaussian-4, multireference Rayleigh-Schrodinger perturbation theory (RS2, RS2C), and state-averaged multiconfiguration self-consistent-field (SA-MCSCF) ab initio methods. Among 38 production channels, the most energetically accessible reaction path is the three-centered rearrangement of cyanide to isocyanide...
September 27, 2018: Journal of Physical Chemistry. A
Embarek Alwedi, J Armando Lujan-Montelongo, Bhaskar R Pitta, Allen Chao, Rodrigo Cortés-Mejía, Jorge M Del Campo, Fraser F Fleming
Asmic addresses the long-standing challenge of alkylating isocyanides, providing access to isocyanides with diverse substitution patterns. The o-anisylsulfanyl group serves a critical dual role by facilitating deprotonation-alkylation and providing a latent nucleophilic site through an unusual arylsulfanyl-lithium exchange.
September 21, 2018: Organic Letters
Francesca Milocco, Folkert de Vries, Anna Dall'Anese, Vera Rosar, Ennio Zangrando, Edwin Otten, Barbara Milani
Palladium(ii) complexes with a bidentate, anionic formazanate ligand are described. Attempts to prepare mono(formazanate) palladium alkyl complexes often leads to the homoleptic bis(formazanate) complex, which shows rich electrochemistry due to the redox-active nature of the ligands. Performing salt metathesis between the precursor [Pd(COD)(CH3)Cl] and the potassium salt of the ligand in the presence of tetrabutylammonium chloride yields a square planar mono(formazanate) palladate complex through coordination of chloride anion...
September 5, 2018: Dalton Transactions: An International Journal of Inorganic Chemistry
Yu-Ying Yang, Xiao-Quan Zhu, Sheng-Min Hu, Shao-Dong Su, Lin-Tao Zhang, Yue-Hong Wen, Xin-Tao Wu, Tian-Lu Sheng
The two stable pairs of trimetallic compounds trans-[Cp*(dppe)Ru(μ-NC)Ru(dmap)4 (μ-CN)Ru(dppe)Cp*][PF6 ]n (1[PF6 ]n , n=2, 3; Cp*=1,2,3,4,5-pentamethylcyclopentadiene; dppe=1,2-bis-(diphenylphosphino)ethane; dmap= 4-dimethylaminopyridine) and trans-[Cp*(dppe)Ru(μ-CN)Ru(dmap)4 (μ-NC)Ru(dppe)Cp*][PF6 ]n (2[PF6 ]n , n=2, 3), which demonstrate cyanide/isocyanide isomerism, have been synthesized and fully characterized. 13+ [PF6 ]3 and 23+ [PF6 ]3 are the one-electron oxidation products of 12+ [PF6 ]2 and 22+ [PF6 ]2 , respectively...
October 22, 2018: Angewandte Chemie
Faeze Khalili, Sara Akrami, Malihe Safavi, Maryam Mohammadi-Khanaposhtanid, Mina Saeedi, Sussan Kabudanian Ardestani, Bagher Larijani, Afsaneh Zonouzi, Maliheh Barazandeh Tehrani, Mohammad Mahdavi
BACKGROUND: This paper reports synthesis, cytotoxic activity, and apoptosis inducing effect of a novel series of styrylimidazo[1,2-a]pyridine derivatives. OBJECTIVE: In this study, anti-cancer activity of novel styrylimidazo[1,2-a]pyridines was evaluated. METHODS: Styrylimidazo[1,2-a]pyridine derivatives 4a-o were synthesized through a one-pot three-component reaction of 2-aminopyridines, cinnamaldehydes, and isocyanides in high yield. All synthesized compounds 4a-o were evaluated against breast cancer cell lines including MDA-MB-231, MCF-7, and T-47D using MTT assay...
September 2, 2018: Anti-cancer Agents in Medicinal Chemistry
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