Org. and Biomol. Chem.

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Pd(II)-Catalyzed Controllable C-H Mono-/Diarylation of Aryl Tetrazoles: Concise Synthesis of Losartan

25 January, 2015 - 07:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02453B, CommunicationXi-Sheng Wang, Yan-Jun Ding, Yan Li, Sheng-Yu Dai, Quan Lan
A palladium(II)-catalyzed C-H arylation directed by tetrazole, a metabolically stable surrogate for the carboxylic acid group in drug design, has been developed. Excellent mono-/di-selectivity was achieved through the protecting site...
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Synthesis of Allylated Quinolines/Isoquinolines via Palladium-Catalyzed Cyclization-Allylation of Azides and Allyl Methyl Carbonate

25 January, 2015 - 07:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02567A, PaperJiang Luo, Zhibao Huo, Jun Fu, Fangming Jin, Yoshinori Yamamoto
A novel and efficient strategy for the one-step synthesis of allylated quinolines and isoquinolines via palladium-catalyzed cyclization-allylation of azides and allyl methyl carbonate is first developed. The results indicated that...
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Copper(II) Bromide-catalyzed Intramolecular Decarboxylative Functionalization to Form C(sp3)-O Bond for the Synthesis of Furo[3,2-c]coumarins

25 January, 2015 - 07:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02490G, PaperWenli Zhang, Shuning Yue, Yongmiao Shen, Huayou Hu, Qinghua Meng, Hui Wu, Yun Liu
An efficient and eco-friendly copper(II) bromide-catalyzed intramolecular decarboxylative functionalization to form C(sp3)-O bond for the synthesis of furo[3,2-c]coumarins has been developed. The transformation is proposed to proceed via a catalytically...
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Copper-Catalyzed Ring Expansion of 2-Aminobenzothiazoles with Alkynyl Carboxylic Acids to 1,4-Benzothiazines

25 January, 2015 - 07:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02467B, PaperJing-Wen Qiu, Bolun Hu, Xing-Guo Zhang, Riyuan Tang, Ping Zhong, Jin-Heng Li
A ring expansion of 2-aminobenzothiazoles with alkynyl carboxylic acids was developed, which allows for one-pot synthesis of 1,4-benzothiazines in moderate to excellent yields. The cascade reaction was achieved through decarboxylative...
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Ylide Formal [4+1] Annulation

25 January, 2015 - 07:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02556C, Review ArticleChunyin Zhu, Ya Ding, Long-Wu Ye
Over the past decades, ylide chemistry has been significantly extended to the area beyond olefination and small ring formation, among which ylide [4+1] annulation has been extensively explored, and five-member...
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Efficient Phosphine ligands for the One-Pot Palladium-Catalyzed Borylation/Suzuki-Miyaura Cross-coupling Reaction

25 January, 2015 - 07:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02436B, PaperYou Chen, Hui Peng, Yunxiao Pi, Tong Meng, Zeyu Lian, Meng-Qi Yan, Yan Liu, Shenghua Liu, Guang-Ao Yu
We report the synthesis of 2-(anthracen-9-yl)-1H-inden-3-yl dicyclohexylphosphine and its use in palladium-catalyzed borylation/Suzuki-Miyaura cross-coupling reaction to prepare a variety of symmetrical and unsymmetrical biaryl compounds in excellent yield.
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Chiral Nanostructuring of Multivalent Macrocycles in Solution and on Surfaces

25 January, 2015 - 07:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02643H, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Marco Caricato, Arnaud Delforge, Davide Bonifazi, Daniele Dondi, Andrea Mazzanti, Dario Pasini
We describe the design and synthesis of a novel functionality-rich, homochiral macrocycle, possessing overall molecular D2 symmetry, in which multivalency is introduced into the covalent framework by means of four...
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Enantioselective Synthesis of 4-Substituted Tetrahydroisoquinolines via Palladium-Catalyzed Intramolecular Friedel-Crafts Type Allylic Alkylation of Phenols

25 January, 2015 - 07:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02574A, PaperShuli You, Zheng-Le Zhao, Qing-Long Xu, Qing Gu, Xin-Yan Wu
Palladium-catalyzed asymmetric intramolecular Friedel-Crafts type allylic alkylation reaction of phenols has been developed under mild conditions. In the presence of Pd2(dba)3 with (1R, 2R)-DACH-phenyl Trost ligand (L2) in toluene at...
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Synthesis and evaluation of hybrid molecules targeting the vinca domain of tubulin

25 January, 2015 - 07:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02114B, PaperOlga Gherbovet, Pedro Alejandro Sanchez-Murcia, Maria Concepcion Garcia-Alvarez, Jerome Bignon, Sylviane Thoret, F Gago, Fanny Roussi
Hybrids of vinca alkaloids and phomopsin A, linked by a glycine pattern, have been synthetized in one or two steps, by an original insertion reaction. These compounds have been elaborated...
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B(C6F5)3-catalyzed metal-free hydrogenation of naphthylamines

25 January, 2015 - 07:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00009B, CommunicationGen Li, Yongbing Liu, HAIFENG DU
A catalytic metal-free hydrogenation of naphthylamines using B(C6F5)3 as a catalyst was successfully achieved under mild conditions for the first time to furnish a variety of tetrahydronaphthylamines in 88-99% yields.
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Hydroboration Reaction as a Key for a Straightforward Synthesis of New MRI-NCT agents

25 January, 2015 - 07:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02291B, PaperAnnamaria Deagostino, Paolo Boggio, Simonetta Geninatti, Diego Alberti, Cristina Prandi, Claudio Medana, Domenica Marabello, Silvio Aime, Paolo Venturello, Antonio Toppino
In this study the hybroboration reaction has been exploited to produce in only four steps a new lipophilic GdBNCT/MRI agent (PB01). As a matter of fact, the formation of a...
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Synthesis of 2-aryl-3-(2-cyanoethyl)aziridines and their chemical and enzymatic hydrolysis towards [gamma]-lactams and [gamma]-lactones

25 January, 2015 - 07:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02615B, PaperKaren Mollet, Lena Decuyper, Saskia Vander Meeren, Nicola Piens, Karel De Winter, Tom Desmet, Matthias D'hooghe
Trans- and cis-2-aryl-3-(2-cyanoethyl)aziridines were transformed into 4-[aryl(alkylamino)methyl]butyrolactones and/or 5-[aryl(hydroxy)methyl]pyrrolidin-2-ones via chemical and enzymatic hydrolysis of the cyano group, followed by ring expansion.
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From [small alpha]-nucleophiles to functionalized aggregates: exploring the reactivity of hydroxamate ion towards esterolytic reactions in micelles

25 January, 2015 - 07:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02067G, Review ArticleNamrata Singh, Yevgen Karpichev, Rahul Sharma, Bhanushree Gupta, Arvind K. Sahu, Manmohan L. Satnami, Kallol K. Ghosh
Hydroxamate ions as [small alpha]-nucleophiles for esterolytic reactions in water and micelles.
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Transition-Metal-Free C-H Oxidative Activation: Persulfate-Promoted Selective Benzylic Mono- and Difluorination

25 January, 2015 - 07:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02418D, CommunicationWen-Bin Yi, Chun Cai, Jing-jing Ma, Guo-ping Lu
An operationally simple and selective method for the direct conversion of benzylic C-H to C-F to get the mono- and difluoromethylated arenes using SelecfluorTM as a fluorine source was developed....
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Exploring the relationship between conformation and pKa: Can a pKa value be used to determine the conformational equilibrium?

25 January, 2015 - 07:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02630F, PaperJacob Ingemar Olsen, Stephan Sauer, Christian Marcus Pedersen, Mikael Bols
Four substituted cis and trans-4,5-dihydroxyhexahydropyridazines that were expected to undergo pH induced conformational switching were synthesized and carefully investigated by NMR analyzes and calculations. For two of the compounds a...
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Xanthenones: Calixarenes-catalyzed Syntheses, Anticancer Activity and QSAR Studies

25 January, 2015 - 07:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02611J, PaperDaniel L. da Silva, Bruna Silva Terra, Mateus Ribeiro Lage, Ana Lucia Ruiz, Cameron Capeletti da Silva, Joao Carvalho, J. Walkimar de M. Carneiro, Felipe Terra Martins, Sergio Antonio Fernandes, Angelo de Fatima
An efficient method is proposed for obtaining tetrahydrobenzo[a]xanthene-11-ones and tetrahydro-[1,3]-dioxolo[4,5-b]xanthen-9-ones. The method is based on the use of p-sulfonic acid calix[n]arenes as catalysts under solvent-free condition.The antiproliferative activity of fitity-nine...
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Enantio-pure synthesis of dihydrobenzo[1,4]-oxazine-3-carboxylic acids and approach to benzoxazinyl oxazolidinones

25 January, 2015 - 07:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02475C, PaperRajesh Malhotra, Tushar K Dey, Sourav Basu, Saumen Hajra
A two steps protocol is developed for the efficient synthesis of enantiopure N-Boc-dihydrobenzo[b]-1,4-oxazine-3-carboxylic acids 4 from serine derived cyclic sulfamidate via intramolecular arylamination. RuPhospalladacycle alongwith additional RuPhos ligand is found...
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In situ activation of benzyl alcohols with XtalFluor-E: formation of 1,1-diarylmethanes and 1,1,1-triarylmethanes through Friedel-Crafts benzylation

25 January, 2015 - 07:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02655A, CommunicationJustine Desroches, Pier Alexandre Champagne, Yasmine Benhassine, Jean-Francois Paquin
The Friedel-Crafts benzylation of arenes using benzyl alcohols activated in situ with XtalFluor-E is described. A wide range of 1,1-diarylmethanes and 1,1,1-triarylmethanes were prepared under simple and mild conditions, without the need for a transition metal or a strong Lewis acid.
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A new multicomponent reaction: Unexpected formation of derivatizable cyclic [small alpha]-alkoxy isothioureas

25 January, 2015 - 07:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02608J, PaperFabian Brockmeyer, Valentin Morosow, Jurgen Martens
An unexpected formation of cyclic [small alpha]-alkoxy isothioureas has been achieved. As is known, the heterocyclic imines 2,5-dihydro-1,3-thiazoles are convertible to bisamides with the aid of a carboxylic acid and an...
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Computational design of novel peptidomimetic inhibitors of cadherin homophilic interactions

25 January, 2015 - 07:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02538E, CommunicationFabio Doro, Cinzia Colombo, Chiara Alberti, Daniela Arosio, Laura Belvisi, Cesare Casagrande, Roberto Fanelli, Leonardo Manzoni, Emilio Parisini, Umberto Piarulli, Elena Luison, Mariangela Figini, Antonella Tomassetti, Monica Civera
Peptidomimetic 3 mimicking the DWVI adhesive sequence of the cadherin EC1 domain inhibits cadherin-mediated adhesion in epithelial ovarian cancer cells.
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