Royal Society of Chemistry

Palladium-catalyzed ortho-acylation of 2-benzyl-1,2,3-triazoles with aldehydes

Org. and Biomol. Chem. - 16 September, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,7474-7477
DOI: 10.1039/C4OB01406E, CommunicationQingshan Tian, Ping He, Chunxiang Kuang
A palladium-catalyzed ortho-acylation of 2-benzyl-1,2,3-triazoles with aldehydes as an acyl source was developed. A wide variety of ketones containing 1,2,3-triazoles were obtained in good to excellent yields. This methodology provides a convenient access to the acylation of 2-substituted-1,2,3-triazoles.
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Preparation, anti-trypanosomal activity and localisation of a series of dipeptide-based vinyl sulfones

Org. and Biomol. Chem. - 16 September, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,7561-7571
DOI: 10.1039/C4OB01412J, PaperWilliam Doherty, Jinju James, Paul Evans, Laura Martin, Nikoletta Adler, Derek Nolan, Andrew Knox
An improved, Weinreb amide-based, synthesis of anti-trypanosomal lysine-containing vinyl sulfones is described incorporating, as a feature, diversity at the [varepsilon]-lysine amino group.
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Rhodium-catalyzed olefination of aryl tetrazoles via direct C-H bond activation

Org. and Biomol. Chem. - 16 September, 2014 - 00:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01440E, CommunicationLiang Wang, Wenting Wu, Qun Chen, Mingyang He
Rh(III)-catalyzed direct olefination reaction via aromatic C-H bond activation is described using tetrazole as the directing group.
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Oxidative cleavage of benzylic C-N bonds under metal-free conditions

Org. and Biomol. Chem. - 16 September, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,7486-7488
DOI: 10.1039/C4OB01633E, CommunicationJin-Long Gong, Xinxin Qi, Duo Wei, Jian-Bo Feng, Xiao-Feng Wu
An interesting and practical metal-free strategy has been developed for the synthesis of aromatic aldehydes using various N,N-dimethylbenzylamines as starting materials.
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Efficient cobalt-catalyzed C-N cross-coupling reaction between benzamide and aryl iodide in water

Org. and Biomol. Chem. - 16 September, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,7478-7481
DOI: 10.1039/C4OB01483A, CommunicationBryan Yong-Hao Tan, Yong-Chua Teo
A practical and efficient strategy for the N-arylation of benzamide catalysed by a Co(C2O4)[middle dot]2H2O/dmeda system in water is reported. Under the optimized conditions, a wide variety of N-arylated products were obtained in good yields (up to 92%) using substituted aryl iodides.
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Influence of B-ring modifications on proton affinity, transmembrane anion transport and anti-cancer properties of synthetic prodigiosenes

Org. and Biomol. Chem. - 16 September, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,7515-7522
DOI: 10.1039/C4OB01399A, PaperEstelle Marchal, Soumya Rastogi, Alison Thompson, Jeffery T. Davis
We describe how modulating the pKa of a family of synthetic prodigiosenes, modified on their B-ring, can control the transmembrane transport of anions.
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Diastereoselective synthesis of functionalized pyrrolidines through N-bromosuccinimide-induced aziridine ring expansion cascade of cinnamylaziridine

Org. and Biomol. Chem. - 16 September, 2014 - 00:54

Org. Biomol. Chem., 2014, 12,7482-7485
DOI: 10.1039/C4OB01384K, CommunicationJing Zhou, Ying-Yeung Yeung
An efficient aziridine ring expansion cascade of cinnamylaziridine has been developed using N-bromosuccinimide as the promoter.
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Synthesis of tumor-associated MUC1-glycopeptides and their multivalent presentation by functionalized gold colloids

Org. and Biomol. Chem. - 16 September, 2014 - 00:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01339E, PaperIsabella Tavernaro, Sebastian Hartmann, Laura Sommer, Heike Hausmann, Christian Rohner, Martin Ruehl, Anja Hoffmann-Roeder, Sabine Schlecht
The authors present the synthesis of novel MUC1-glycopeptide antigens and their multivalent presentation by gold colloids. Their biological activity was tested in a dot-blot immunoassay experiment.
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Silver-catalyzed carbonphosphonation of [small alpha],[small alpha]-diaryl allylic alcohols: synthesis of [small beta]-aryl-[gamma]-ketophosphonates

Org. and Biomol. Chem. - 16 September, 2014 - 00:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01739K, CommunicationXia Mi, Chenyang Wang, Mengmeng Huang, Yusheng Wu, Yangjie Wu
Silver-catalyzed carbonphosphonation of [small alpha],[small alpha]-diaryl allylic alcohols was achieved. A series of [gamma]-ketophosphonates with different substituents were readily obtained. Mechanistic study indicated that the reaction was initiated by the addition of...
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5-Nitroindole oligonucleotides with alkynyl side chains: universal base pairing, triple bond hydration and properties of pyrene "click" adducts

Org. and Biomol. Chem. - 16 September, 2014 - 00:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01478B, PaperFrank Seela, Sachin Asaram Ingale, Peter Leonard, Haozhe Yang
Oligonucleotides with 3-ethynyl-5-nitroindole and 3-octadiynyl-5-nitroindole 2'-deoxyribonucleosides were prepared by solid-phase synthesis. To this end, nucleoside phosphoramidites with clickable side chains were synthesized. The 3-ethynylated 5-nitroindole nucleoside was hydrated during automatized...
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Stability and bioactivity of thrombin binding aptamers modified with D-/L-isothymidine in the loop regions

Org. and Biomol. Chem. - 16 September, 2014 - 00:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01525H, PaperBaobin Cai, Xiantao Yang, Lidan Sun, Xinmeng Fan, Liyu Li, Hongwei Jin, Yun Wu, Zhu Guan, Liangren Zhang, Li-He Zhang, Zhenjun Yang
Thrombin binding aptamer (TBA) is a 15-mer single-strand DNA that was identified by SELEX screening technology. It adopts a chair-type antiparallel G-quadruplex and can specifically interact with thrombin, thus inhibiting...
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Imides Modified Benzopicenes: Synthesis, Solid Structure and Optoelectronic Properties

Org. and Biomol. Chem. - 16 September, 2014 - 00:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01486C, PaperJun Yin, Di Wu, Haojie Ge, zhao chen, Jinhua Liang, Jie Huang, Yufeng Zhang, Xiaoqiang Chen, Xiang-Gao Meng, Shenghua Liu
Imide-modified polycyclic aromatic hydrocarbons can be widely applied in the field of optoelectronic materials. In this work, we have synthesized four novel functionalized benzopicenes and characterized their solid structures and...
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Highly Enantioselective Phosphination and Hydrophosphonylation of Azomethine Imines: Using Chiral Squaramide as Hydrogen Bonding Organocatalyst

Org. and Biomol. Chem. - 16 September, 2014 - 00:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01472C, PaperLing-Pei Kong, Nai-Kai Li, Shao-Yun Zhang, Xiang Chen, Min Zhao, Ya-Fei Zhang, Xingwang Wang
Enantioselective phosphination and hydrophosphonylation reactions between azomethine imines and diaryl phosphine oxides and dialkyl phosphites are respectively developed by the use of a chiral squaramide as the hydrogen bonding organocatalyst,...
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Transition-metal-free synthesis of 3-Aryol-4-methyl(or benzyl)-2-(methylthio) furans from [small alpha]-oxo Ketene dithioacetals and propargyl alcohols via the Domino coupling/annulations

Org. and Biomol. Chem. - 16 September, 2014 - 00:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01300J, PaperFangzhong Hu, Xiaobing Yang, Hongjing Di, Xinxin Cheng, Dan Li, Xiaoli Kan, Xiaomao Zou, Qichun Zhang
A new strategy (transitional-metal-free catalysis) to synthesize 3-aryol- 4-methyl (or benzyl)-2-methylthio furans 2 (trisubstituted furans) has been developed through the domino coupling/annulations from available -oxo ketene dithioacetals 1 and propargyl...
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Utilizing Electrostatic Interactions to Facilitate F-18 Radiolabeling of Poly(amido)amine (PAMAM) Dendrimers

Org. and Biomol. Chem. - 16 September, 2014 - 00:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01616E, PaperDong Zhou, Sung Hoon Kim, Vincent M Carroll, Carmen S Dence, John Katzenellenbogen
The development of methods for the facile conjugation and radiolabeling of poly(amido)amine (PAMAM) dendrimers would be of great benefit in evaluating biomedical applications of these intriguing molecularly defined polymers. Two...
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Anion binding of a neutral bis(cyclopeptide) in water/methanol mixtures containing up to 95% of water

Org. and Biomol. Chem. - 16 September, 2014 - 00:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01497A, PaperFabian Sommer, Stefan Kubik
Anion receptor 2b was designed and synthesized that structurally derives from a previously described bis(cyclopeptide) 2a comprising two covalently linked cyclic hexapeptide rings with alternating L-proline and 6-aminopicolinic acid subunits....
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The journey of L-tartaric acid in the world of enantiomerically pure bis- and trisadducts of C60 with the inherently chiral trans-3 and all-trans-3 addition patterns

Org. and Biomol. Chem. - 16 September, 2014 - 00:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01666A, PerspectiveNikos Chronakis
Inherently chiral multi-adducts of [60]fullerene represent unique chiral molecular tectons featuring fascinating optoelectronic properties. Herein we discuss the most recent progress in the synthesis of enantiomerically pure bis- and trisadducts...
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First Principles Calculation of Electron Ionization Mass Spectra for Selected Organic Drug Molecules

Org. and Biomol. Chem. - 16 September, 2014 - 00:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01668H, PaperChristoph Alexander Bauer, Stefan Grimme
This study presents a showcase for the novel Quantum Chemistry Electron Ionization Mass Spectrometry (QCEIMS) method on five FDA-approved drugs. The method allows a first-principles electronic structure-based prediction of EI...
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Thiophene-benzoquinones: synthesis, crystal structures and preliminary coordination chemistry of derived anilate ligands

Org. and Biomol. Chem. - 16 September, 2014 - 00:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01582G, PaperMatteo Atzori, Flavia Pop, Thomas Cauchy, Maria Laura Mercuri, Narcis Avarvari
2,5-bis(thiophene) and 2,5-bis(ethylenedioxy-thiophene) (EDOT) derivatives of 3,6-diethoxy-1,4-benzoquinone (para isomers) have been prepared by Stille coupling between the 2,5-dibromo-3,6-diethoxy-1,4-benzoquinone precursors and (n-Bu)3Sn-R (R = 2-thiophenyl or 3,4-ethylenedioxy-2-thiophenyl) reagents. In a parallel...
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An efficient route to synthesize isatins by metal-free, iodine-catalyzed sequential C(sp3)-H oxidation and intramolecular C-N bond formation of 2'-aminoacetophenones

Org. and Biomol. Chem. - 16 September, 2014 - 00:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01564A, PaperVenkatachalam Rajeshkumar, Chandrasekar S., G Sekar
A novel molecular I2-catalyzed synthesis of isatins through C(sp3)-H oxidation and intramolecular C-N bond formation of 2'-aminoacetophenones with excellent yields up to 97 % under transition-metal, base, additive, peroxide and...
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