Royal Society of Chemistry

Palladium-catalyzed arylation of 2H-chromene: a new entry to pyrano[2,3-c]carbazoles

Org. and Biomol. Chem. - 31 August, 2015 - 13:54

Org. Biomol. Chem., 2015, 13,9285-9293
DOI: 10.1039/C5OB01295C, PaperK. Ranjith Reddy, A. Siva Reddy, Devendra K. Dhaked, S. K. Rasheed, Anup Singh Pathania, Ravi Shankar, Fayaz Malik, Parthasarathi Das
Various pyrano[2,3-c]carbazoles are synthesized in high yields over five steps from commercially available resorcinol. Palladium-catalyzed arylation remains a key step in this novel strategy. The versatility of this protocol has been demonstrated by the first total synthesis of naturally occurring carbazole clauraila C.
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Understanding the conformational behaviour of Ac-Ala-NHMe in different media. A joint NMR and DFT study

Org. and Biomol. Chem. - 31 August, 2015 - 13:54

Org. Biomol. Chem., 2015, 13,9206-9213
DOI: 10.1039/C5OB01296A, PaperRodrigo A. Cormanich, Michael Buhl, Roberto Rittner
The conformational behaviour of Ac-Ala-NHMe is investigated in the gas-phase and in nonpolar, polar and polar protic solutions by experimental 1H NMR and theoretical calculations.
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Metal-free cycloaddition to synthesize naphtho[2,3-d][1,2,3]triazole-4,9-diones

Org. and Biomol. Chem. - 31 August, 2015 - 13:54

Org. Biomol. Chem., 2015, 13,9261-9266
DOI: 10.1039/C5OB01322D, PaperPing-Fan Chen, Kung-Kai Kuo, Jaya Kishore Vandavasi, Siva Senthil Kumar Boominathan, Chung-Yu Chen, Jeh-Jeng Wang
A metal-free domino [3 + 2] cycloaddition is reported to construct naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives and provide an alternative approach to the azide-alkyne cycloadditions.
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Calix[4]arene triazole-linked pyrene: click synthesis, assembly on graphene oxide, and highly sensitive carbaryl sensing in serum

Org. and Biomol. Chem. - 31 August, 2015 - 13:54

Org. Biomol. Chem., 2015, 13,9294-9299
DOI: 10.1039/C5OB01388G, PaperYue Sun, Xiaowei Mao, Li Luo, Demei Tian, Haibing Li
Graphene oxide modified with a fluorescent calix[4]arene showed a highly selective recognition for carbaryl.
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Micellization properties of cardanol as a renewable co-surfactant

Org. and Biomol. Chem. - 31 August, 2015 - 13:54

Org. Biomol. Chem., 2015, 13,9214-9222
DOI: 10.1039/C5OB01059D, PaperAntonella Fontana, Susanna Guernelli, Nelsi Zaccheroni, Romina Zappacosta, Damiano Genovese, Lucia De Crescentini, Serena Riela
Hydrogenated cardanol (HC) is used as a green additive for commercial surfactants. A percentage as high as 10% of HC does not affect commercial surfactant properties although it significantly increases their sustainability.
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Ruthenium-catalyzed cyclization of N-carbamoyl indolines with alkynes: an efficient route to pyrroloquinolinones

Org. and Biomol. Chem. - 31 August, 2015 - 13:54

Org. Biomol. Chem., 2015, 13,9276-9284
DOI: 10.1039/C5OB01146A, PaperRamasamy Manoharan, Masilamani Jeganmohan
A regioselective synthesis of substituted pyrroloquinolinones by a ruthenium-catalyzed oxidative cyclization of substituted N-carbamoyl indolines with alkynes is described.
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Triazole linker-based trivalent sialic acid inhibitors of adenovirus type 37 infection of human corneal epithelial cells

Org. and Biomol. Chem. - 31 August, 2015 - 13:54

Org. Biomol. Chem., 2015, 13,9194-9205
DOI: 10.1039/C5OB01025J, PaperRemi Caraballo, Michael Saleeb, Johannes Bauer, A. Manuel Liaci, Naresh Chandra, Rickard J. Storm, Lars Frangsmyr, Weixing Qian, Thilo Stehle, Niklas Arnberg, Mikael Elofsson
Adenovirus type 37 (Ad37) is one of the principal agents responsible for epidemic keratoconjunctivitis (EKC), a severe ocular infection that remains without treatment.
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Synthesis of a new class of iminosugars based on constrained azaspirocyclic scaffolds by way of catalytic C-H amination

Org. and Biomol. Chem. - 31 August, 2015 - 13:54

Org. Biomol. Chem., 2015, 13,9176-9180
DOI: 10.1039/C5OB01254F, CommunicationPierre-Antoine Nocquet, Raphael Hensienne, Joanna Wencel-Delord, Eric Wimmer, Damien Hazelard, Philippe Compain
High level of regiocontrol has been achieved in the C-H amination of substrates with a high density of reactive C-H bonds, allowing the access to a new class of conformationally constrained iminosugars.
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Synthesis and investigation of singlet oxygen production efficiency of photosensitizers based on meso-phenyl-2,5-thienylene linked porphyrin oligomer and polymers

Org. and Biomol. Chem. - 31 August, 2015 - 13:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB01435B, PaperDonus Tuncel, MUAZZAM IDRIS, REHAN KHAN
Three new Zn(II)- oligo- and poly(2,5-thienylene)-linked porphyrins, bearing multiple triethylene glycol (TEG) groups, on all meso aryl positions were synthesized via Stille and Suzuki coupling reactions and their photophysical properties...
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A dual optical and nuclear imaging reagent for peptide labelling via disulfide bridging

Org. and Biomol. Chem. - 31 August, 2015 - 13:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB01468A, CommunicationSally A. Fletcher, Pak Kwan Brian Sin, Muriel Nobles, Erik Arstad, Andrew Tinker, James R. Baker
We report a concise approach to a multimodal imaging reagent for peptide labelling via disulfide bridging. The reagent is constructed using a one pot, three component, [3 + 2] cycloaddition of a fluorescent azide with a dithiomaleimide-alkyne, with concomitant incorporation of 125I.
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Pd Catalyzed Insertion of Alkynes into Cyclic Diaryliodoniums: A Direct Access to Multi-substituted Phenanthrenes

Org. and Biomol. Chem. - 31 August, 2015 - 13:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB01597A, PaperShijun Wen, Yongcheng Wu, Fu-Hai Wu, Daqian Zhu, Bingling Luo, Haiwen Wang, Yumin Hu, Peng Huang
Cyclic diaryliodoniums remain unexplored compared to linear iodoniums. In our current work, internal alkynes were for the first time applied to react with cyclic iodoniums, catalyzed by Pd, resulting in...
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Dithiafulvenyl-substituted phenylacetylene derivatives: synthesis and structure-property-reactivity relationships

Org. and Biomol. Chem. - 31 August, 2015 - 13:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB01651G, CommunicationYunfei Wang, Yuming Zhao
A series of regioisomers for dithiafulvenyl-substituted phenylacetylene derivatives was synthesized and characterized to show structure-dependent electronic properties and different reactivity in their oxidized states.
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Helical peptaibol mimics are better ionophores when racemic than when enantiopure

Org. and Biomol. Chem. - 31 August, 2015 - 13:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB01652E, CommunicationSarah J Pike, Jennifer E Jones, James Raftery, Jonathan Clayden, Simon Webb
Helical peptide foldamers rich in [small alpha]-aminoisobutyric acid (Aib) act as peptaibol-mimicking ionophores in the phospholipid bilayers of artificial vesicles. Racemic samples of these foldamers are more active than their enantiopure...
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Gold(I) catalysed sequential dehydrative cyclisation/ intermolecular [4+2] cycloaddition of alkynyldienols onto activated alkynes/ alkenes: A facile route to substituted norbornadienes/norbornenes

Org. and Biomol. Chem. - 31 August, 2015 - 13:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB01458A, PaperK. C. Kumara Swamy, Anasuyamma Uruvakili, G. Gangadhararao
One-pot synthesis of highly substituted norbornadienes/ norbornenes via gold-catalysed dehydrative cyclisation of alkynyldienol, followed by intermolecular [4+2] cycloaddition of in situ generated cyclopentadiene and activated alkynes/ alkenes is described. The...
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Paley's watchmaker analogy and prebiotic synthetic chemistry in surfactant assemblies. Formaldehyde scavenging by pyrroles leading to porphyrins as a case study

Org. and Biomol. Chem. - 31 August, 2015 - 13:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB01409C, PaperEric J. Alexy, Carl W. Hintz, Hubert M. Hughes, Masahiko Taniguchi, Jonathan S. Lindsey
Facile exchange of micromolar dialkylpyrrolic constituents among a Poisson distribution of aqueous micelles overcomes immense statistical odds against reaction.
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Synthesis and photophysical properties of pyrene-labeled 3-deaza-2'-deoxyadenosines comprising a non-[small pi]-conjugated linker: Fluorescence quenching-based oligodeoxynucleotide probes for thymine identification

Org. and Biomol. Chem. - 31 August, 2015 - 13:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB01605C, PaperTatsuya Aso, Koichiro Saito, Azusa Suzuki, Yoshio Saito
Pyrene-labeled 3-deaza-2'-deoxyadenosine comprising a non-[small pi]-conjugated linker py3zA (1) was synthesized and its photophysical properties were investigated. Oligodeoxynucleotide (ODN) probes containing py3zA (1) exhibited remarkable fluorescence quenching only when the opposite...
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Pd(OAc)2‑Catalysed Regioselective Alkoxylation of Aryl ([small beta]-carbolin-1-yl) methanones via [small beta]-Carboline directed ortho-C(sp2)-H activation of aryl ring

Org. and Biomol. Chem. - 31 August, 2015 - 13:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB01500F, PaperShivalinga Kolle, Sanjay Batra
Synthesis of (2-alkoxyphenyl)(9H-pyrido[3,4-b]indol-1-yl)methanone via Pd(OAc)2-catalyzed regioselective alkoxylation of aryl ([small beta]-carbolin-1-yl) methanones employing [small beta]-carboline directed ortho-C(sp2)-H activation of aryl ring under oxidative conditions is described.
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Effects of multivalent histamine supported on gold nanoparticles: activation of histamine receptors by derivatized histamine at subnanomolar concentrations

Org. and Biomol. Chem. - 31 August, 2015 - 13:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB01354B, PaperFriederike Gasiorek, Ervice Pouokam, Martin Diener, Sabine Schlecht, Mathias S. Wickleder
Gold nanoparticles were functionalized with native histamine. The multivalent presentation resulted in extremely low activation concentration for histaminic receptors.
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Enamine/Butadienylborane Cycloaddition in the Frustrated Lewis Pair Regime

Org. and Biomol. Chem. - 31 August, 2015 - 13:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB01602A, PaperGerald Kehr, G Erker, Stefan Grimme, Christoph Bannwarth, Constantin Gabriel Daniliuc, Fatma Turkyilmaz, Guo-Qiang Chen
The dienylborane 2a was prepared by regioselective alkyne hydroboration of the conjugated enyne 1a with Piers' borane [HB(C6F5)2]. Its reaction with a series of acetophenone derived enamines 3 resulted in...
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Palladium-Catalyzed One-Pot Synthesis of diazoles via tert-Butyl Isocyanide Insertion

Org. and Biomol. Chem. - 31 August, 2015 - 13:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB01328C, PaperYong-Ming Zhu, Xiang-Yuan Fan, Xiao Jiang, Zhen-Bang Chen, Ying Zhang
An efficient one-pot palladium-catalyzed reaction for the synthesis of diazoles from readily available hydrazides and aryl halide via isocyanide insertion/cyclization sequence has been developed. This methodology efficiently constructs diazoles in...
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