Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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1,8-Bis(phenylethynyl)anthracene - gas and solid phase structures

28 July, 2015 - 05:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB01078K, PaperJan-Hendrik Lamm, Jan Horstmann, Hans-Georg Stammler, Norbert W. Mitzel, Yuriy A. Zhabanov, Natalya V. Tverdova, Arseniy A. Otlyotov, Nina I. Giricheva, Georgiy V. Girichev
The structure of 1,8-bis(phenylethynyl)anthracene has been studied in detail in the gas phase and the solid state by a combined GED/MS method and by XRD of a single crystal. Arylaryl interactions are discussed in terms of dispersive forces.
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One-pot synthesis of 1,3-enynes with a CF3 group on the terminal sp2 carbon by an oxidative Sonogashira cross-coupling reaction

28 July, 2015 - 05:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB01290B, PaperAkari Ikeda, Masaaki Omote, Kana Kusumoto, Atsushi Tarui, Kazuyuki Sato, Akira Ando
One-pot synthesis of 1,3-enynes with a CF3 group on the terminal sp2 carbon was achieved by an oxidative Sonogashira cross-coupling reaction with (E)-trimethyl(3,3,3-trifluoroprop-1-enyl)silane.
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Photochemically-induced C-C bond formation between tertiary amines and nitrones

28 July, 2015 - 05:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB01277E, PaperKennosuke Itoh, Ryo Kato, Daito Kinugawa, Hideaki Kamiya, Ryuki Kudo, Masayuki Hasegawa, Hideaki Fujii, Hiroyuki Suga
Photoexcited nitrones serve as excellent electron acceptors as well as radical acceptors in the presence of tertiary amines to give [small beta]-amino hydroxylamines via photochemically-induced direct sp3 C-H functionalization of the tertiary amines.
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Stereoselective [small alpha]-indolylation of enals via an organocatalytic formal cross-coupling with indoles

28 July, 2015 - 05:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB01360G, PaperYang Hu, Lei Ju, Lin Lu, Hongmei Ma, Xinhong Yu
A novel organocatalytic one-pot cascade bromination-Michael addition dearomatization-nucleophilic rearrangement aromatization cascade process for the direct [small alpha]-indolylation of unfunctionalized enals from readily available indoles with good yields and high E selectivity has been developed with great simplicity and practicality.
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2-Oxo promoted hydrophosphonylation & aerobic intramolecular nucleophilic displacement reaction

28 July, 2015 - 05:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB01310K, CommunicationSatyanarayana Battula, Narsaiah Battini, Deepika Singh, Qazi Naveed Ahmed
Highly efficient catalyst free methods for the synthesis of [small alpha]-hydroxy-[small beta]-oxo phosphonates (HOP) and [small alpha]-oxoesters (OE) have been described for the first time. The existence of a 2-oxo group in [small alpha]-oxoaldehydes (OA) was a key factor in promoting the reaction of the tervalent phosphite form towards activated aldehydes (OA) in the synthesis of HOP.
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Rapid optimization of labeled ubiquitinated peptides for monitoring deubiquitinases activities

28 July, 2015 - 05:54

Org. Biomol. Chem., 2015, 13,8182-8186
DOI: 10.1039/C5OB01142F, CommunicationShimrit Ohayon, Maya Refua, Ashraf Brik
A new synthetic approach is reported which enables the rapid synthesis of labeled-ubiquitinated peptides to facilitate optimization of deubiquitinases substrates.
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Towards more drug-like proteomimetics: two-faced, synthetic [small alpha]-helix mimetics based on a purine scaffold

28 July, 2015 - 05:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00478K, CommunicationM. E. Lanning, P. T. Wilder, H. Bailey, B. Drennen, M. Cavalier, L. Chen, J. L. Yap, M. Raje, S. Fletcher
Key residues on opposing faces of the Bak-BH3 [small alpha]-helix were recapitulated by the 2,6,9-tri-substitution of a purine scaffold.
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Photoresponsive self-assembled hexameric capsules based on calix[4]resorcinarenes bearing azobenzene dendron conjugates as side chains

28 July, 2015 - 05:54

Org. Biomol. Chem., 2015, 13,8359-8364
DOI: 10.1039/C5OB00997A, PaperTsubasa Sakano, Toshifumi Ohashi, Masamichi Yamanaka, Kenji Kobayashi
Calix[4]resorcinarenes with azobenzene dendron conjugates achieve control of the assembly-disassembly-reassembly process of the hydrogen-bonded hexameric capsules by a light stimulus.
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De novo synthesis of phenolic dihydroxanthene near-infrared emitting fluorophores

28 July, 2015 - 05:54

Org. Biomol. Chem., 2015, 13,8169-8172
DOI: 10.1039/C5OB01223F, CommunicationJean-Alexandre Richard
We report a flexible de novo synthesis of phenolic dihydroxanthenes in 60-70% yield thanks to a one-pot cascade sequence.
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Unified mild reaction conditions for C2-selective Pd-catalysed tryptophan arylation, including tryptophan-containing peptides

28 July, 2015 - 05:54

Org. Biomol. Chem., 2015, 13,8298-8309
DOI: 10.1039/C5OB01174D, PaperAlan J. Reay, Thomas J. Williams, Ian J. S. Fairlamb
Mild Pd-mediated C-H functionalisation protocols, facilitating tryptophan C2-arylation, have been developed. Tryptophan-containing peptides, susceptible to oxidation, have been arylated.
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Oligoethylene glycol-substituted aza-BODIPY dyes as red emitting ER-probes

28 July, 2015 - 05:54

Org. Biomol. Chem., 2015, 13,8271-8276
DOI: 10.1039/C5OB01104C, PaperAnyanee Kamkaew, Sopida Thavornpradit, Thamon Puangsamlee, Dongyue Xin, Nantanit Wanichacheva, Kevin Burgess
This study features aza-BODIPY (BF2-chelated azadipyrromethene) dyes with two aromatic substituents linked by oligoethylene glycol fragments to increase hydrophilicity of aza-BODIPY for applications in intracellular imaging.
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Mechanistic insight into conjugated N-N bond cleavage by Rh(III)-catalyzed redox-neutral C-H activation of pyrazolones

28 July, 2015 - 05:54

Org. Biomol. Chem., 2015, 13,8251-8260
DOI: 10.1039/C5OB00977D, PaperWeirong Wu, Yuxia Liu, Siwei Bi
DFT calculations are performed to understand the conjugated N-N bond cleavage by Rh(III)-catalyzed redox-neutral C-H activation of pyrazolones with PhC[triple bond, length as m-dash]CPh.
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Palladium-catalyzed arylation of 2H-chromene: a new entry to pyrano[2,3-c]carbazoles

28 July, 2015 - 05:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB01295C, PaperK Ranjith Kumar, A Siva Reddy, Devendra Kumar Dhaked, Sk. Rasheed, Anup S Pathania, Ravi Shankar, Fayaz Malik, Parthasarathi Das
Pyrano[2,3-c]carbazoles which are biologically valuable and synthetically challenging frameworks are synthesized in high yields over five steps from commercially available resorcinol. Palladium-catalyzed arylation remain a key step in this novel...
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Understanding the conformational behaviour of Ac-Ala-NHMe in different media. A joint NMR and DFT study.

28 July, 2015 - 05:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB01296A, PaperRodrigo A Cormanich, Roberto Rittner, Michael Buhl
The conformational behaviour of Ac-Ala-NHMe was studied in the gas-phase and in solution by theoretical calculations (B3LYP/aug-cc-pVDZ level) and experimental 1H NMR. The conformational preferences of this compound was shown...
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Metal Free Cycloaddition to Synthesize Naphtho[2,3-d][1,2,3]triazole-4,9-diones

28 July, 2015 - 05:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB01322D, PaperBing-Fan Chen, Kung-Kai Kuo, Jaya Kishore Vandavasi, Siva Senthil Kumar Boominathan, Chung-Yu Chen, JJ 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 an alternative approach to the azide-alkyne cycloadditions. The key features are easily available starting materials, mild conditions,...
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Synthesis and antimicrobial potential of nitrofuran-triazole congeners

28 July, 2015 - 05:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB01353D, PaperAhmed Kamal, Mohammed Ali Hussaini Syed, Lakshmi Sucharitha M., Poornachandra Y, Faria Sultana, Ganesh Kumar C.
A series of 5-nitrofuran-triazole congeners were designed and synthesized by carrying out suitable structural modifications of the previously reported counterparts and were evaluated for their antimicrobial potential against both Gram-positive...
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Putting corannulene in its place. Reactivity studies comparing corannulene with other aromatic hydrocarbons

28 July, 2015 - 05:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB01215E, PaperStephen R D George, Thomas D H Frith, Donald S Thomas, Jason B Harper
A series of aromatic hydrocarbons were investigated so as to compare the reactivity of corannulene with planar aromatic hydrocarbons. Corannulene was found to be more reactive than benzene, naphthalene and...
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Calix[4]arene triazole-linked pyrene:click synthesis, assembly on graphene oxide, and highly sensitive carbaryl sensing in serum

28 July, 2015 - 05:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB01388G, PaperHaibing Li, yue sun, Xiaowei Mao, Li Luo, Demei Tian
Fluorescent calix[4]arene triazole-linked pyrene (CP) was carefully designed and synthesized via click chemistry. And CP modified with graphene oxide (GO) by a simple non-covalent interaction strategy is presented. The further...
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Stereoselective Synthesis of Activated 2-Arylazetidines via Imino-Aldol Reaction

28 July, 2015 - 05:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB01140J, PaperManas K. Ghorai, Subhomoy Das, Kalpataru Das, Amit Kumar
A simple and efficient synthetic route to substituted N-sulfinyl and N-sulfonyl azetidines is described involving imino-aldol reaction of ester enolates with racemic and non-racemic aldimines for obtaining [small beta]-amino esters as...
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Synthesis of Chiral Hexacyclic Steroids via [8[small pi]+2[small pi]] Cycloaddition of Diazafulvenium methides

28 July, 2015 - 05:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB01110H, PaperSusana M. M. Lopes, Catia F. O. Correia, Sandra C. C. Nunes, Nelson A. M. Pereira, Ana R. F. Ferreira, Emanuel P. Sousa, Clara S. B. Gomes, Jorge A. R. Salvador, Alberto Canelas Pais, Teresa M. V. D. Pinho e Melo
First examples of [8[small pi]+2[small pi]] cycloaddition of 16-dehydropregnenolone (16-DPA) acetate with diazafulvenium methides leading to chiral 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-fused steroids are reported. These hexacyclic steroids were obtained exclusively or selectively with the approach...
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