Org. and Biomol. Chem.

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Synthesis of meta and para-substituted aromatic sulfonate derivatives of polydentate phenylazaphosphinate ligands: enhancement of the water solubility of emissive europium(III) EuroTracker[registered sign] dyes

2 October, 2014 - 04:54

Org. Biomol. Chem., 2014, 12,8061-8071
DOI: 10.1039/C4OB01143K, PaperMartina Delbianco, Laurent Lamarque, David Parker
The use of a trifluoroethyl ester group to protect sulfonic acid moieties is used in the synthesis of a short series of water-soluble, very bright europium(III) complexes.
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Zinc mediated activation of terminal alkynes: stereoselective synthesis of alkynyl glycosides

2 October, 2014 - 04:54

Org. Biomol. Chem., 2014, 12,7900-7903
DOI: 10.1039/C4OB01405G, CommunicationMadhu Babu Tatina, Anil Kumar Kusunuru, Syed Khalid Yousuf, Debaraj Mukherjee
Zinc mediated alkynylation reaction was studied for the preparation of C-glycosides from unactivated aromatic and aliphatic acetylenes. Different glycosyl donors such as glycals and anomeric acetates were tested towards in situ generated alkynyl zinc reagent using zinc dust and ethyl bromoacetate. The method provides a simple, mild and stereoselective access of alkynyl glycosides.
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Conformational effects due to stereochemistry and C3-substituents in xylopyranoside derivatives as studied by NMR spectroscopy

2 October, 2014 - 04:54

Org. Biomol. Chem., 2014, 12,8031-8035
DOI: 10.1039/C4OB01422G, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Jerk Ronnols, Sophie Manner, Ulf Ellervik, Goran Widmalm
Dynamic NMR spectroscopy revealed an unequally populated equilibrium at low temperature for a 3-deoxygenated compound.
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The importance of chain conformational mobility during 5-exo-cyclizations of C-, N- and O-centred radicals

2 October, 2014 - 04:54

Org. Biomol. Chem., 2014, 12,7983-7992
DOI: 10.1039/C4OB01419G, PaperJohn C. Walton
The access angle of a radical centre to an alkene acceptor was found to be a key parameter that pinpointed difficult chain reorganizations as responsible for the slow 5-exo cyclizations of N-centred radicals.
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The coumarin-pterocarpan conjugate - a natural product inspired hybrid molecular probe for DNA recognition

2 October, 2014 - 04:54

Org. Biomol. Chem., 2014, 12,8087-8093
DOI: 10.1039/C4OB01360C, PaperShital K. Chattopadhyay, Indranil Kundu, Ratnava Maitra
Thermally induced cascade sigmatropic rearrangement of a butynyloxycoumarin derivative has led to a quick access to the coumarin-pterocarpan hybrid molecule. Biophysical studies together with molecular modeling show that this nature-inspired hybrid molecule is capable of binding to the minor groove of DNA as a non-conventional entity.
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Metal-free, one-pot conversion of proline derivatives into 2-ary-3-iodo pyrrolidines, by a sequential scission-iodination-arylation process

30 September, 2014 - 04:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01372G, PaperAlicia Boto, Ivan Romero-Estudillo, Venkateswara Rao Batchu, Javier Miguelez
The metal-free, direct conversion of readily available proline derivatives into 2-aryl-3-iodopyrrolidines is carried out under mild conditions and good yields, using a sequential radical decarboxylation-oxidation-iodination-arylation reaction. These iodinated pyrrolidines are...
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Synthesis of substituted quinolines via allylic amination and intramolecular Heck-coupling

30 September, 2014 - 04:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01614A, PaperSiva Murru, Brandon McGough, Radhey S. Srivastava
New catalytic approach to access substituted quinolines and naphthyridines via allylic C-H amination followed by intramolecular Heck-coupling and aerobic dehydrogenation.
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Short and efficient synthesis of fluorinated [small delta]-lactams

30 September, 2014 - 04:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01547A, PaperThomas J. Cogswell, Craig S. Donald, De-Liang Long, Rodolfo Marquez
The diastereoselective synthesis of fluorinated [small delta]-lactams.
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A Lewis acid-mediated conformational switch

30 September, 2014 - 04:17

Org. Biomol. Chem., 2014, 12,7937-7941
DOI: 10.1039/C4OB01556H, PaperPeter C. Knipe, Hannah Lingard, Ian M. Jones, Sam Thompson, Andrew D. Hamilton
An isonicotinamide-substituted diphenylacetylene undergoes conformational switching upon recognition of Lewis acids.
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Neither azeotropic drying, nor base nor other additives: a minimalist approach to 18F-labeling

30 September, 2014 - 04:17

Org. Biomol. Chem., 2014, 12,8094-8099
DOI: 10.1039/C4OB01336K, PaperR. Richarz, P. Krapf, F. Zarrad, E. A. Urusova, B. Neumaier, B. D. Zlatopolskiy
A novel radiofluorination procedure using only precursor and [18F]fluoride without the need for azeotropic drying, base and other ingredients was developed.
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The origin of exo-stereoselectivity of norbornene in hetero Diels-Alder reactions

30 September, 2014 - 04:17

Org. Biomol. Chem., 2014, 12,8079-8086
DOI: 10.1039/C4OB01217H, PaperSesil Agopcan Cinar, Selami Ercan, Sule Erol Gunal, Ilknur Dogan, Viktorya Aviyente
The distortion of norbornene and the steric effect of the quasi-eclipsing forming bonds in the endo transition structures were demonstrated successfully in order to highlight the exo selectivity of norbornene in the reaction of 5-benzylidine-2-arylimino-3-aryl-thiazolidine-4-thiones with norbornene with the M06-2X/6-31+G(d)//B3LYP/6-31+G(d) methodology.
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Non-isoprenoid polyene natural products - structures and synthetic strategies

30 September, 2014 - 04:17

Org. Biomol. Chem., 2014, 12,7877-7899
DOI: 10.1039/C4OB01337A, Review ArticleKatrina S. Madden, Fathia A. Mosa, Andrew Whiting
This review provides insight into the variety of structures and biological activities found in the non-isoprenoid family of polyene natural products and examines the strategies and synthetic methods applied for the polyenic components in particular by way of examples.
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Enantioselective aza-Morita-Baylis-Hillman reaction between acrylates and N-Boc isatin ketimines: asymmetric construction of chiral 3-substituted-3-aminooxindoles

30 September, 2014 - 04:17

Org. Biomol. Chem., 2014, 12,8072-8078
DOI: 10.1039/C4OB01358A, PaperXuan Zhao, Tian-Ze Li, Jing-Ying Qian, Feng Sha, Xin-Yan Wu
The first enantioselective aza-Morita-Baylis-Hillman reaction of acrylates with ketimines was achieved in excellent yields and good enantioselectivities.
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Conformationally constrained nucleoside phosphonic acids - potent inhibitors of human mitochondrial and cytosolic 5[prime or minute](3[prime or minute])-nucleotidases

30 September, 2014 - 04:17

Org. Biomol. Chem., 2014, 12,7971-7982
DOI: 10.1039/C4OB01332H, PaperOndrej Simak, Petr Pachl, Milan Fabry, Milos Budesinsky, Tomas Jandusik, Ales Hnizda, Radka Sklenickova, Magdalena Petrova, Vaclav Veverka, Pavlina Rezacova, Jiri Brynda, Ivan Rosenberg
Conformationally constrained nucleoside phosphonic acids - potent inhibitors of human mitochondrial and cytosolic 5[prime or minute](3[prime or minute])-deoxynucleotidases.
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Asymmetric Michael addition of ketones to nitroolefins: pyrrolidinyl-oxazole-carboxamides as new efficient organocatalysts

30 September, 2014 - 04:17

Org. Biomol. Chem., 2014, 12,8008-8018
DOI: 10.1039/C4OB01223B, PaperAhmed Kamal, Manda Sathish, Vunnam Srinivasulu, Jadala Chetna, Kunta Chandra Shekar, Shalini Nekkanti, Yellaiah Tangella, Nagula Shankaraiah
New pyrrolidinyl-oxazole-carboxamides were synthesized and utilized as efficient organocatalysts for asymmetric Michael addition reaction. In addition, computational mechanistic studies were performed.
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Multiple optical properties of a naphthoquinone pigment: 2-methyl-3-(hydroxyphenylthio)-1,4-naphthalenedione

30 September, 2014 - 04:17

Org. Biomol. Chem., 2014, 12,7965-7970
DOI: 10.1039/C4OB01058B, PaperHirotaka Akiyama, Takafumi Inoue, Nobuo Tajima, Reiko Kuroda, Yoshitane Imai
Naphthoquinone pigments 2-methyl-3-(4- or 2-hydroxyphenylthio)-1,4-naphthalenedione show characteristic multiple optical properties in solution and in the solid state.
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Pyrazole-oxadiazole conjugates: synthesis, antiproliferative activity and inhibition of tubulin polymerization

30 September, 2014 - 04:17

Org. Biomol. Chem., 2014, 12,7993-8007
DOI: 10.1039/C4OB01152J, PaperAhmed Kamal, Anver Basha Shaik, Sowjanya Polepalli, Vangala Santosh Reddy, G. Bharath Kumar, Soma Gupta, K. V. S. Rama Krishna, Ananthamurthy Nagabhushana, Rakesh K. Mishra, Nishant Jain
A library of pyrazole-oxadiazole conjugates were synthesized and investigated for their antiproliferative activity in human cancer cell lines.
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Rhodium-catalyzed olefination of aryl tetrazoles via direct C-H bond activation

30 September, 2014 - 04:17

Org. Biomol. Chem., 2014, 12,7923-7926
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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Discovery and SAR study of piperidine-based derivatives as novel influenza virus inhibitors

30 September, 2014 - 04:17

Org. Biomol. Chem., 2014, 12,8048-8060
DOI: 10.1039/C4OB01079E, PaperGuoxin Wang, Longjian Chen, Tongmei Xian, Yujie Liang, Xintao Zhang, Zhen Yang, Ming Luo
A series of 4-(quinolin-4-yloxy)piperidine-1-carboxylate derivatives were identified as novel and potent inhibitors of the influenza virus through structural modification of a compound from a high-throughput screen.
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An experimental and theoretical study of reaction mechanisms between nitriles and hydroxylamine

30 September, 2014 - 04:17

Org. Biomol. Chem., 2014, 12,8036-8047
DOI: 10.1039/C4OB00854E, PaperAttila Voros, Zoltan Mucsi, Zoltan Baan, Geza Timari, Istvan Hermecz, Peter Mizsey, Zoltan Finta
The industrially relevant reaction between nitriles and hydroxylamine yielding amidoximes was studied in different molecular solvents and in ionic liquids.
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