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Xiuting Chen, Qingnuan Li, Lester Andrews, Yu Gong
A series of group 3 metal isocyanide complexes were prepared via the reactions of laser ablated scandium, yttrium and lanthanum atoms with (CN)2 in an argon matrix. The product structures were identified on the basis of their characteristic infrared absorptions from isotopically labeled (CN)2 samples as well as the calculated frequencies and isotopic frequency ratios. Group 3 metal atoms reacted with (CN)2 to form M(NC)2 (M=Sc, Y, La) when the samples were subjected to >220 nm irradiation. Other products such as M(NC)3 and MNC were produced together with M(NC)2 through either the reactions of M(NC)2 and (CN)2 or the loss of one CN ligand from M(NC)2...
August 13, 2018: Journal of Physical Chemistry. A
Nelson R Vinueza, Bartłomiej J Jankiewicz, Vanessa A Gallardo, John J Nash, Hilkka I Kenttämaa
Two previously unreported isomeric biradicals with a 1,4-radical topology, the 1,5-didehydroisoquinolinium cation and the 4,8-didehydroisoquinolinium cation, and an additional, previously reported isomer, the 4,5-didehydroisoquinolinium cation, were studied to examine the importance of the exact location of the radical sites on their reactivities in the gas phase. The experimental results suggest that hydrogen bonding in the transition state enhances the reactivity of the 1,5-didehydroisoquinolinium cation towards tetrahydrofuran but not towards allyl iodide, dimethyl disulfide or tert-butyl isocyanide...
August 10, 2018: Physical Chemistry Chemical Physics: PCCP
Xiao-Ying Huang, Rui Ding, Zu-Yu Mo, Yan-Li Xu, Hai-Tao Tang, Heng-Shan Wang, Yan-Yan Chen, Ying-Ming Pan
An unexpected cyclization of thioamides with p-quinone methides promoted by acridinium salt under the irradiation of visible light furnished 1,2,4-dithiazoles in moderate to good yields. In addition, the reaction of the obtained 1,2,4-dithiazoles with isocyanides offered a new entry for the synthesis of thiazol-5(4 H)-imines in moderate yields.
August 8, 2018: Organic Letters
Danil P Zarezin, Olga I Shmatova, Valentine G Nenajdenko
An efficient three-step synthesis of a novel family of enantiomerically pure isocyanides derived from β3-isocyanopropionic acids was elaborated. Easily available N-formylated α-amino acids were used as starting materials towards this aim. The 3-step sequence (Arndt-Eistert reaction-Wolff rearrangement-dehydration) resulted in target isonitriles in good yields (up to 97%). As a result a new family of isocyanides bearing a fragment of β3-amino acids with different functional groups (amides, esters and short peptides) was obtained...
August 7, 2018: Organic & Biomolecular Chemistry
Xingxing Ma, Yao Zhou, Qiuling Song
An efficient and practical strategy for the synthesis of β-aminoenones from a three-component reaction was developed. Ethyl bromodifluoroacetate serves as a C1 source in this strategy, forming isocyanides in situ with primary amines. This reaction represents the first example of utilization of readily available starting materials to generate isocyanides in situ and sequentially fully converted to β-aminoenones, avoiding the generation of byproduct imines and overinsertion products. The mechanism study suggested that this method involves activation of two C(sp3 )-F bonds and the formation of isocyanides, which might nourish both isocyanide chemistry and fluorine chemistry...
August 1, 2018: Organic Letters
Ramdas S Pathare, Arshad J Ansari, Sarika Verma, Anand Maurya, Antim K Maurya, Vijai K Agnihotri, Ashoke Sharon, Ram T Pardasani, Devesh M Sawant
A rapid and efficient synthesis of aminotetrazole from aryl azides, isocyanides, and TMSN3 is developed. The reaction is promoted by sequential Pd(0)/Fe(III) catalysis. The reaction sequence utilizes the Pd-catalyzed azide-isocyanide denitrogenative coupling reaction to generate unsymmetric carbodiimide in situ, which reacts with TMSN3 in the presence of FeCl3 in a single pot. The methodology has distinct advantages over traditional synthetic approaches where toxic Hg and Pb salts are employed at stoichiometric scale...
August 6, 2018: Journal of Organic Chemistry
Karel Skoch, Ivana Cisarova, Petr Stepnicka
The newly discovered gold-catalysed reaction of isocyanides with hydrazoic acid generated in situ from trimethylsilyl azide and methanol (or, alternatively, from NaN3/AcOH) produces either cyanamides or 1-substituted 1H-tetrazol-5-amines, depending on the amount of available HN3. The reaction proceeds selectively and in generally high yields of either product, thus providing a particularly convenient access to a wide range of substituted 1H-tetrazol-5-amines that are rather difficult to access otherwise.
July 23, 2018: Chemistry: a European Journal
Lan-Gui Xie, Darren J Dixon
Amides are ubiquitous in the fine chemical, agrochemical and pharmaceutical industries, but are rarely exploited as substrates for homologous amine synthesis. By virtue of their high chemical stability, they are essentially inert to all but the harshest of chemical reagents and to the majority of chemical transformations routinely used in organic synthesis. Accordingly, the development of chemoselective carbon-carbon bond-forming methodologies arising from the functionalization of the amide functionality should find widespread use across academia and industry...
July 19, 2018: Nature Communications
Łukasz Kruszewski, Monika J Fabiańska, Justyna Ciesielczuk, Tomasz Segit, Ryszard Orłowski, Rafał Motyliński, Danuta Kusy, Izabela Moszumańska
A methodological approach to the complex geochemical analysis of the coal fire in burning coal mine heaps (BCMH) of Upper Silesian Coal Basin has been developed. The other approach used is gas chromatography and indicatory tubes. Powder X-Ray Diffraction is applied for phase analysis to determine the species composition of mineral condensates present within and around gas flues. The gas compositions are proved to be extremely variable, when comparing both different BCMH and flues or flue zones of the same heaps...
November 1, 2018: Science of the Total Environment
Philippe Schollhammer, Federica Arrigoni, Salma Mohamed Bouh, Catherine Elleouet, François Pétillon, Luca De Gioia, Giuseppe Zampella
Electrochemical oxidation of the complex [Fe2(CO)4(κ2-dmpe)(µ-adtBn)] (adtBn = (SCH2)2NCH2C6H5, dmpe = Me2PCH2CH2PMe2) (1) has been studied by cyclic voltammetry (CV) in acetonitrile and in dichloromethane in presence of various substrates L (L =MeCN, trimethylphosphite, isocyanide). The oxidized species, [1-MeCN](PF6)2, [1-(P(OMe)3)2](PF6)2 and [1-(RNC)4](PF6)2 (R = tButyl, Xylyl), have been prepared and characterized by IR, NMR spectroscopies and, excepted [1-MeCN](PF6)2, by X-ray diffraction analysis. The crystallographic structures of the new FeIIFeII complexes reveal in any case that the association of one additional ligand (P(OMe)3 or RNC) occurs and, according to the nature of the substrates, further substitutions of one or three carbonyl groups, by P(OMe)3 or RNC, respectively, arise...
July 16, 2018: Chemistry: a European Journal
N Esmati, A R Maddirala, N Hussein, H Amawi, A K Tiwari, P R Andreana
A one-pot, two-step, total synthesis of naturally occurring xenortides A, B, C and D, (Xens A-D) isolated from the bacterium Xenorhabdus nematophila, and an entire complementary set of stereoisomers, has been achieved. Compounds were synthesized utilizing an isocyanide-based Ugi 4-CR followed by facile N-Boc deprotection. The reaction sequence took advantage of the chiral pool of N-Boc protected amino acids (l-Leu/Val and d-Leu/Val) with aryl isocyanides, phenyl acetaldehyde and methylamine giving the desired Xens A-D (A and B >98% ee) and all subsequent stereoisomers in reasonable yields upon deprotection followed by separation of diastereomers...
July 25, 2018: Organic & Biomolecular Chemistry
Ya-Hao Wang, Miao-Miao Liang, Yue-Jiao Zhang, Shu Chen, Petar Radjenovic, Hua Zhang, Zhi-Lin Yang, Xiao-Shun Zhou, Zhong-Qun Tian, Jian-Feng Li
Heterogeneous metal interfaces play a key role in determining the mechanism and performance of catalysts. However, in situ characterization of such interfaces at the molecular level is challenging. Herein, two model interfaces, Pd and Pt overlayers on Au single crystals, were constructed. The electronic structures of these interfaces as well as effects of crystallographic orientation on them were analyzed by shell-isolated nanoparticle-enhanced Raman spectroscopy (SHINERS) using phenyl isocyanide (PIC) as a probe molecule...
July 11, 2018: Angewandte Chemie
Porag Bora, Ghanashyam Bez
Insertion of isocyanides into the N-H bond gives access to many medicinally important and structurally diverse complex nitrogen-containing heterocycles. Although the transition metal catalyzed isocyanide insertion into the N-H bond is very common, polymerization of isocyanides in the presence of a transition metal and their strong coordination with metals are the common drawbacks. On the other hand, the inertness of most of the isocyanides towards amines in the absence of a metal catalyst has stymied the growth of the metal-free approach for isocyanide insertion into amines...
July 24, 2018: Chemical Communications: Chem Comm
Angelica Mariani, David A Russell, Thomas Javelle, John D Sutherland
Investigations into the chemical origin of life have recently benefitted from a holistic approach in which possible atmospheric, organic, and inorganic systems chemistries are taken into consideration. In this way, we now report that a selective phosphate activating agent, namely methyl isocyanide, could plausibly have been produced from simple prebiotic feedstocks. We show that methyl isocyanide drives the conversion of nucleoside monophosphates to phosphorimidazolides under potentially prebiotic conditions and in excellent yields for the first time...
July 18, 2018: Journal of the American Chemical Society
Vijay Nair, Rajeev S Menon
A number of well-known reactions, proceed through the intermediacy of dipolar/zwitterionic species generated via the addition of a neutral nucleophile with an unsaturated electrophile. A mechanistic understanding of these reactions was made possible by seminal contributions of Huisgen. The design of novel reactions based on such dipolar species was, however, not pursued in detail for a long time. Our efforts to exploit various reactivity profiles available for the zwitterionic/dipolar intermediates have resulted in the discovery of a large number of novel, convenient protocols to access a wide variety of products...
July 2, 2018: Chemical Record: An Official Publication of the Chemical Society of Japan ... [et Al.]
Chun Qian, Kui Liu, Shou-Wei Tao, Fang-Ling Zhang, Yong-Ming Zhu, Shi-Lin Yang
A novel palladium-catalyzed oxidative three-component coupling of easily accessible N-substituted anthranilamides with isocyanides and arylboronic acids is achieved. This protocol offers an alternative approach toward 2,3-disubstituted quinazolinones with a wide substrate scope and good functional group tolerance.
July 12, 2018: Journal of Organic Chemistry
Yue Fang, Zheng-Yang Gu, Shun-Yi Wang, Jin-Ming Yang, Shun-Jun Ji
A Co-catalyzed effective synthesis of N-sulfonylcarboxamides from the reaction of carboxylic acids and organic azides in the presence of isocyanide has been developed. The protocol has the advantages of short time, low temperature, and being oxidant-free, which provides a new and simple approach for the synthesis of N-sulfonylcarboxamides in good to excellent yields with a broad substrate scope.
July 11, 2018: Journal of Organic Chemistry
Ali Asghar Mohammadi, Salman Taheri, Arman Amini, Reza Ahdenov
Triamide derivatives have been synthesized in good yields in a novel, one-pot, five-component, and efficient process by the reaction of Z-oxazolone, water, primary amines, aldehydes, isocyanides, in the presence of catalytic amount of KAl(SO4 )2 ·12H2 O (alum) as a non-toxic, reusable, inexpensive, and easily available reagent via Ugi reaction in aqueous solution.
June 27, 2018: Molecular Diversity
Charalampos Triantis, Antonio Shegani, Christos Kiritsis, Myrto Ischyropoulou, Ioanna Roupa, Vassilis Psycharis, Catherine Raptopoulou, Patricia Kyprianidou, Maria Pelecanou, Ioannis Pirmettis, Minas S Papadopoulos
The synthesis and characterization of the dicarbonyl mixed ligand cis-[Re(CO)2 (quin)(cisc)(PPh3 )] complex, 4, where quin is the deprotonated quinaldic acid, cisc is cyclohexyl isocyanide, and PPh3 is triphenylphosphine, is presented. The synthesis of 4 proceeds in three steps. In the first, the intermediate fac-[Re(CO)3 (quin)(H2 O)] aqua complex 2 is generated from the fac-[NEt4 ]2 [Re(CO)3 Br3 ] precursor, together with the brominated products fac-[Re(CO)3 (quinH)(Br)] 1a and fac-[NEt4 ][Re(CO)3 (quin)(Br)] 1b, in low yield...
July 16, 2018: Inorganic Chemistry
Sonia Moreno, Alberto Ramos, Fernando Carrillo-Hermosilla, Antonio Rodríguez-Diéguez, Daniel García-Vivó, Rafael Fernández-Galán, Antonio Antiñolo
A selective three-component coupling was employed to fix carbon dioxide to boron guanidinato compounds. The one-pot reaction of carbon dioxide, carbodiimides, and borylamines (ArNH)BC8 H14 afforded the corresponding 1,2-adducts {R(H)N}C{N(Ar)}(NR)(CO2 )BC8 H14 . Alternatively, the reaction with p-MeOC6 H4 NC or 2,6-Me2 C6 H3 NC gave the corresponding isocyanide 1,1-adducts { i-PrHN}C{N(p-Me-C6 H4 )}(N i-Pr){CNAr}BC8 H14 . The molecular structures of products (2,6- i-Pr2 C6 H3 NH)BC8 H14 7, { i-Pr(H)N}C{N(p-MeC6 H4 )}(N i-Pr)(CO2 )BC8 H14 9, {Cy(H)N}C{N( p-MeC6 H4 )}(Cy)(CO2 )BC8 H14 13, and { i-PrHN}C{N( p-MeC6 H4 )}(N i-Pr){CNR″}BC8 H14 (R″ = p-MeOC6 H4 , 2,6-Me2 C6 H3 ) 14 and 15 were established by X-ray diffraction...
July 16, 2018: Inorganic Chemistry
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