Royal Society of Chemistry

Synthesis and Characterization of a Highly Strained Donor-Acceptor Nanohoop

Org. and Biomol. Chem. - 7 February, 2016 - 03:17
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C6OB00133E, PaperJeff Van Raden, Evan Rashied Darzi, Lev Zakharov, Ramesh Jasti
A highly-strained, nitrogen-doped cycloparaphenylene (CPP), aza[6]CPP, was synthesized and then converted to a donor-acceptor nanohoop, N-methylaza[6]CPP, via alkylation of the nitrogen center. The energy levels of the lowest unoccupied molecular...
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Recent progress in imidoyl radical-involved reactions

Org. and Biomol. Chem. - 7 February, 2016 - 03:17
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C6OB00087H, Review ArticleJian Lei, Jinbo Huang, Qiang Zhu
Much attention has been paid in imidoyl radical-involved reactions in recent years. As a divergent reactive intermediate, imidoyl radicals are used for the synthesis of functionalized heterocycles, nitriles, amides, or...
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Efficient one-pot synthesis of 1-arylcycloprop-2-ene-1-carboxamides

Org. and Biomol. Chem. - 7 February, 2016 - 03:17
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C6OB00156D, PaperAndrew Stephen Edwards, Michael Rubin
An expeditious and cost-efficient method for synthesis of 1-aryl-cycloprop-2-ene-1-carboxamides was developed. This one-pot protocol involving coupling of amines with acyl chlorides, generated upon treatment of cyclopenylcarboxylic acids with oxalyl chloride,...
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A novel pyrimidine tetrad contributing to stabilize tetramolecular G-quadruplex structures

Org. and Biomol. Chem. - 7 February, 2016 - 03:17
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C5OB02358K, PaperAldo Galeone, Veronica Esposito, Antonietta Pepe, Rosanna Filosa, Luciano Mayol, Antonella Virgilio
G-quadruplex structures formed by oligodeoxyribonucleotides TGGUNH2GGT (AM, UNH2 = 5-amino-2'-deoxyuridine), TGGUBrGGT (BR, UBr = 5-bromo-2'-deoxyuridine) and TGGTGGT (TH) have been investigated through circular dichroism, nuclear magnetic resonance, gel electrophoresis and...
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Palladium-Catalyzed Direct Arylation of Indoles with Arylsulfonyl Hydrazides

Org. and Biomol. Chem. - 7 February, 2016 - 03:17
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C5OB02569A, CommunicationCongrong Liu, Lianghui Ding, Guang Guo, Weiwei Liu, Fu-Lai Yang
A novel method to synthesis 2-arylindoles is demonstrated via direct arylation of indoles with arylsulfonyl hydrazides. Under the optimized reaction conditions, the reaction well tolerates a wide variety of functional...
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Influence of conjugation and other structural changes on the activity of Cu2+ based PNAzymes

Org. and Biomol. Chem. - 7 February, 2016 - 03:17
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C5OB02394G, PaperAlice Ghidini, Merita Murtola, Roger Stromberg
We have previously shown that PNA-neocuproine conjugates can act as artificial RNA restriction enzymes. In the present study we have additionally conjugated the PNA with different entities, such as oligoethers,...
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Sulfuration of C(sp2)-H Bond of Enaminones: A Protocol for The Synthesis of Thioether Using Elemental Sulfur as Sulfurating Reagent

Org. and Biomol. Chem. - 7 February, 2016 - 03:17
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C5OB02619A, PaperLi-Fang Yang, Cheng-Guo Liu, Xiao-Ping Xu, Shun-Jun Ji
Sulfuration reaction of C(sp2)-H bond of enaminones with elemental sulfur in the presence of CuBr/K3PO4 was carried out. It provided an efficient method for the synthesis of thioethers in moderate...
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Ir(III)-Catalyzed C-H Alkynylation of Arenes under Chelation Assistance

Org. and Biomol. Chem. - 7 February, 2016 - 03:17
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C6OB00106H, PaperGuo-Dong Tang, Chengling Pan, Fang Xie
An efficient and mild Ir(III)-catalyzed, chelation assisted C-H alkynylation of arenes has been developed using hypervalent iodine alkynes as alkynylating reagents. A broad scope of N-phenyl-2-aminopyridines and 2-phenoxypyridines has been...
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Phage-displayed macrocyclic glycopeptide libraries

Org. and Biomol. Chem. - 7 February, 2016 - 03:17
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C5OB02646F, CommunicationSimon Ng, Ratmir Derda
In this report, we describe an efficient way to generate libraries of macrocyclic glycopeptides in one step by reacting phage-displayed libraries of peptides with dichloro-oxime derivatives. We showed that the...
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Simple assembly of polysubstituted pyrazoles and isoxazoles via ring closure-ring opening domino reaction of 3-acyl-4,5-dihydrofurans with hydrazines and hydroxylamine

Org. and Biomol. Chem. - 7 February, 2016 - 03:17
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C5OB02596F, PaperAlexey Chagarovskiy, Ekaterina Budynina, Olga Ivanova, Victor Borisovich Rybakov, Igor Trushkov, Mikhail Ya. Melnikov
А convenient general approach to 2-(pyrazol-4-yl)- and 2-(isoxazol-4-yl)ethanols based on the Bronsted acid-initiated reaction of 3-acyl-4,5-dihydrofurans with hydrazines or hydroxylamine was developed. Further transformation of the alcohol moiety in 2-(pyrazolyl)ethanols...
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Phthalocyanine-cRGD Conjugate: Synthesis, Photophysical Properties and in vitro Biological Activity for Targeting Photodynamic Therapy

Org. and Biomol. Chem. - 7 February, 2016 - 03:17
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C6OB00099A, PaperLiqiang Luan, Wenjuan Fang, Wei Liu, Minggang Tian, Yuxing Ni, Xi Chen, Xiaoqiang Yu
An unsymmetrical phthalocyanine conjugated with an RGDyK moiety (6) was synthesized and characterized. Its photophysical properties, including electronic absorption, fluorescence emission ([capital Phi]F = 0.20), singlet oxygen quantum yield ([capital Phi]∆ =...
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Extending the corrole ring conjugation: preparation of [small beta],[small beta]'-fused 2,3-[1',2'-b]pyrazinocorroles

Org. and Biomol. Chem. - 7 February, 2016 - 03:17
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C5OB02572A, PaperBeatrice Berionni Berna, Sara Nardis, Federica Mandoj, Frank R Fronczek, Kevin M Smith, Roberto Paolesse
A novel method for the preparation of corroles with [small beta]-fused pyrazino rings was developed, exploiting a one-pot reaction of 2,3-diaminocorroles (or 2,3,17,18-tetraaminocorroles) with different diones;a variety of [small pi]-extended corroles were...
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Nazarov cyclization of divinyl ketones bearing ester group at [small beta]-position: remarkable effect of [small alpha]-substitution and alkene geometry on regioselectivity

Org. and Biomol. Chem. - 7 February, 2016 - 03:17
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C6OB00081A, PaperSudhakar Gangarajula, Raghavaiah Jakka, Mahesh Gaddam, Kiran Kumar Singarapu
Nazarov cyclization of divinyl ketones with an ester in the [small beta]-position was examined with particular reference to where the cyclic double bond forms. We observed unprecedented regioselectivity, dictated by the...
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Search for Blues Brothers: X-ray Crystallographic/Spectroscopic Characterization of Tetraarylbenzidine Cation Radical as a Product of Aging of Solid Magic Blue

Org. and Biomol. Chem. - 7 February, 2016 - 03:17
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C6OB00140H, PaperMarat Talipov, Mohammad M Hossain, Anitha Boddeda, Khushabu Thakur, Rajendra Rathore
Magic blue (MB+[round bullet, filled] SbCl6- salt), i.e. tris-4-bromophenylamminium cation radical, is a routinely employed one-electron oxidant that slowly decomposes in solid state upon storage to form so called 'blues brothers', which...
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Palladium-Catalyzed Paraformaldehyde Insertion: A Three-Component Synthesis of Benzofurans

Org. and Biomol. Chem. - 7 February, 2016 - 03:17
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C6OB00198J, CommunicationGuo-Jun Deng, Xiufang Cheng, Yi Peng, Jun Wu
An efficient procedure for 2-aroylbenzofuran preparation from 2-bromophenols, phenacyl bromides and paraformaldehyde is described. The cheap and stable paraformaldehyde served as the carbon source via in situ formylation reaction.
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Regioselective ortho-trifluoromethylthiolation of 2-arylbenzo[d]thiazole via tandem substrate-assisted C-H iodination and trifluoromethylthiolation

Org. and Biomol. Chem. - 7 February, 2016 - 03:17
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C6OB00005C, PaperPuying Luo, Qiuping Ding, Yuanyuan Ping, Jianan Hu
A mild and efficient tandem benzo[d]thiazole directed C-H iodination and trifluoromethylthiolation for the synthesis of ortho-trifluoromethylthiolated 2-arylbenzo[d]thiazoles has been developed using AgSCF3 as coupling partner. The reaction exhibits a diverse...
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Total Facial Selectivity of a D-Erythrosyl Aromatic Imine in [4[small pi]+2[small pi]] Cycloadditions; Synthesis of 2-Alkylpolyol 1,2,3,4-Tetrahydroquinolines

Org. and Biomol. Chem. - 7 February, 2016 - 03:17
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C5OB02594J, PaperMaria Jose Alves, Antonio Gil Fortes, Juliana Ferreira, Jennifer Noro, Vera Duarte
Different electron-rich dienophiles were combined with the imine obtained from 2,4-O-benzylidene-D-erythrose and p-anisidine furnishing enantiomerically pure tetrahydroquinolines, by inverse electron-demand [4[small pi]+2[small pi]] cycloaddition. The imine was also reacted with 2-substituted electron-rich...
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Triggering the approach of an Arene or Heteroarene towards an aldehyde via Lewis acid-aldehyde communication

Org. and Biomol. Chem. - 7 February, 2016 - 03:17
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C5OB02284C, PaperSanjay Pratihar
The present work involves a combined experimental/computational study on the Lewis acid promoted hydroxyalkylation reaction involving aldehyde and arene/heteroarene and reveals a mechanism in which rate determining aldehyde to alcohol...
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Iodine-Catalyzed Synthesis of Dibenzo[b,h][1,6]naphthyridine-11-carboxamides via a Domino Reaction Involving Double Elimination of Hydrogen Bromide

Org. and Biomol. Chem. - 7 February, 2016 - 03:17
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C5OB02620B, PaperBin-Bin Feng, Chao Li, Lian Lu, Xiang-Shan Wang
An iodine-catalyzed reaction of 2-aminobenzamides and Mucobromic acid was described and utilized to synthesize a variety of 6-oxo-5,6-dihydrodibenzo[b,h][1,6] naphthyridine-11-carboxamide derivatives in refluxing THF. As the two bromine atoms in Mucobromic...
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Rapid and efficient synthesis of [small alpha](1-2)mannobiosides

Org. and Biomol. Chem. - 7 February, 2016 - 03:17
Org. Biomol. Chem., 2016, Accepted Manuscript
DOI: 10.1039/C6OB00083E, PaperJose Juan Reina, Antonio Di Maio, Javier Ramos-Soriano, Rute C. Figueiredo, Javier Rojo
[small alpha](1,2)mannobiosides with different substituents at the reducing end have been synthesized by a common strategy using benzoyls as permanent protecting groups and an acetyl as orthogonal protecting group at position...
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