Royal Society of Chemistry

A General Pd/Cu-Catalyzed C-H Heteroarylation of 3-Bromoquinolin-2(1H)-ones

Org. and Biomol. Chem. - 1 September, 2014 - 21:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01610F, PaperAlexandre BRUNEAU, Jean Daniel BRION, SAMIR MESSAOUDI, Mouad Alami
3-(heteroaryl)quinolin-2(1H)-ones were synthesized in good to excellent yields using a bimetallic catalytic system through C-H heteroarylation strategy. Starting from 3-bromoquinolin-2(1H)-ones, various azoles have been successfully used. In all cases, the...
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Enantioselective Total Syntheses of the Proposed Structures of Prevezol B and Evaluation of Anti-Cancer Activity

Org. and Biomol. Chem. - 1 September, 2014 - 21:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01662A, PaperAnna Leung, Riccardo Rubbiani, Gilles Gasser, Kellie Tuck
The first enantioselective total syntheses of the proposed structures of the natural product prevezol B are reported. The reported syntheses complement the previously-reported syntheses of the proposed structures of prevezol...
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Mechanism and Regioselectivity of Gold (I) or Platinum (II) Catalyzed Intramolecular Hydroarylation to Pyrrolopyridinones and Pyrroloazepinones

Org. and Biomol. Chem. - 1 September, 2014 - 21:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB00894D, PaperRan Fang, Xiaoxiao Wei, Lizi Yang
We report here the theoretical analysis of the mechanism and regioselectivity of gold (I) or platinum (II) catalyzed intramolecular hydroarylation to pyrrolopyridinones and pyrroloazepinones. AuPH3+ and PtCl2 have been considered...
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Direct Synthesis of Polysubstituted 2-Aminothiophenes through Cu(II)-Catalyzed Addition/Oxidative Cyclization of Alkynoates with Thioamides

Org. and Biomol. Chem. - 1 September, 2014 - 21:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01534G, PaperLi-Shi Ge, Zheng-Lin Wang, Xing-Lan An, Xiaoyan Luo, Wei-Ping Deng
A facile and direct synthetic method was developed for the construction of structurally important 2-aminothiophenes in moderate to excellent yields (up to 91%), via Cu(II)-catalyzed addition/oxidative cyclization of readily available...
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Short, Efficient Synthesis of Fluorinated [small delta]-Lactams.

Org. and Biomol. Chem. - 1 September, 2014 - 21:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01547A, PaperRodolfo Marquez, Tom Cogswell, Craig Donald, Deliang Long
The diastereoselective synthesis of fluorinated [small delta]-lactams has been achieved through an efficient five step process. The route can tolerate a range of functionality, and provides a quick route for the...
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Chiroptical molecular propeller based on hexakis(phenylethynyl)benzene through the complexation-induced intramolecular transmission of local point chirality

Org. and Biomol. Chem. - 1 September, 2014 - 21:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01601G, PaperRyo Katoono, Keiichi Kusaka, Shunsuke Kawai, Yuki Tanaka, Keisuke Hanada, Tatsuo Nehira, Kenshu Fujiwara, Takanori Suzuki
We designed hexakis(phenylethynyl)benzene derivatives with a tertiary amide group on each blade to achieve a helically-biased propeller arrangement through the complexation-induced intramolecular transmission of point chirality. A hydrogen-bonding ditopic guest...
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Facile Synthesis of Antimalarial 1,2-Disubstituted 4-Quinolones from 1,3-Bisaryl-monothio-1,3-diketones

Org. and Biomol. Chem. - 1 September, 2014 - 21:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01455C, PaperChanne D Gowda, Maralinganadoddi P Sadashiva, Ajjampura C Vinayaka, Xianzhu Wu, Sergei Biryukov, Jose A Stoute, Kanchugarakoppal S Rangappa
A new strategy was developed to synthesize 1,2-disubstituted 4-quinolones in good yield starting from 1,3-bisaryl-monothio-1,3-diketone substrates. The synthesized compounds were evaluated for antimalarial activity using Plasmodium falciparum strains. All compounds,...
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Synthesis and Photophysical Properties of Pyrene-Based Green Fluorescent Dyes: Butterfly-Shaped Architectures

Org. and Biomol. Chem. - 1 September, 2014 - 21:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01509F, CommunicationDevendar Vanga, Mithun Santra, Ashok Keerthi, Suresh Valiyaveettil
A few pyrene-based fluorescent compounds were synthesized using Pd/Cu-catalyzed cross-coupling reaction. Photophysical properties of the [small pi]-conjugated pyrene derivatives were studied and the results indicate materials with high quantum efficiency and...
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Synthesis of Phenanthridine Derivatives via Cascade Annulation of Diaryliodonium Salts and Nitriles

Org. and Biomol. Chem. - 1 September, 2014 - 21:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01504E, Communicationjian li, hongni wang, Jiangtao Sun, Yang Yang, li liu
A cascade coupling reaction toward a variety of phenanthridine derivatives has been developed. This cascade trans-formation proceeds via the copper-catalyzed coupling reaction of diaryliodonium salts and nitriles, undergoes cyclization into...
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Estimating the shape and size of supramolecular assemblies by variable temperature diffusion ordered spectroscopy

Org. and Biomol. Chem. - 1 September, 2014 - 21:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01373E, CommunicationBenjamin M Schulze, Davita L Watkins, Jing Zhang, Ion Ghiviriga, Ronald K Castellano
Reported is characterization of the self-assembly of [small pi]-conjugated oligomers, molecules studied recently in photovoltaic devices, using variable temperature diffusion ordered spectroscopy (VT-DOSY). Iterative fitting of diffusion coefficient versus temperature data...
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Oxyma-B, an Excellent Racemization Suppressor in Peptide Synthesis

Org. and Biomol. Chem. - 1 September, 2014 - 21:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01612B, CommunicationFernando Albericio, Yahya Jad, Sherine Khattab, Beatriz G. De la Torre, Thavendran Govender, Gert Kruger, Ayman El-Faham
Peptide-bond formation is a key process in the synthesis of peptide oligomers. Among the many coupling techniques reported, carbodiimides combine strong acylation potency and smooth reaction conditions and are commonly...
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Direct C-H Bond Arylation of Fluorenes with Aryl Chlorides Catalyzed by N-Heterocyclic Carbene-Palladium(II)-1-Methylimidazole Complex and Further Transformation of the Products in A One-Pot Procedure

Org. and Biomol. Chem. - 1 September, 2014 - 21:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01594K, PaperYa-Yun Ji, Li-Li Lu, Yu-Chun Shi, Li-Xiong Shao
We report herein the NHC-Pd(II)-Im complex 1 catalyzed direct C-H bond functionalization of C9-position of fluorenes with aryl chlorides and further transformation of the resulting products in a one-pot procedure....
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Concise Synthesis of 2,4-Disubstituted Thiazoles from [small beta]-Azido Disulfides and Carboxylic acids or Anhydrides: Asymmetric Synthesis of Cystothiazole C

Org. and Biomol. Chem. - 1 September, 2014 - 21:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01460J, PaperYi Liu, Xue Sun, Xing Zhang, Jun Liu, Yuguo Du
A novel and efficient method for one-pot synthesis of 2,4-disubstituted thiazoles from carboxylic acids or anhydrides is established. Based on this new methodology, the total synthesis of bis-2,4-disubstituted bis(thiazoles) natural...
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HBTU mediated 1-Hydroxybenzotriazole (HOBt) Conjugate Addition: Synthesis and Stereochemical Analysis of beta-benzotriazole N-oxide Substituted gamma-Amino acids and Hybrid peptides

Org. and Biomol. Chem. - 1 September, 2014 - 21:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01548G, PaperHosahudya N Gopi, Sachitanand M Mali, Mothukuri Ganesh Kumar, Mona M Katariya
HBTU is a standard coupling agent commonly used for the activation of free carboxylic acids during the solution and solid phase peptide synthesis. 1-Hydroxybezotriazole (HOBt) plays a significant role in...
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Catalytic Asymmetric Synthesis of Pentacyclic Core of (-)-Nakadomarin A via Oxazolidine as an Iminium Cation Equivalent

Org. and Biomol. Chem. - 1 September, 2014 - 21:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01678E, CommunicationNobuya Tsuji, Michael Stadler, Naoya Kazumi, Tsubasa Inokuma, Yusuke Kobayashi, Yoshiji Takemoto
A facile and catalytic asymmetric synthesis of the pentacyclic core of (-)-nakadomarin A, containing all the stereogenic centers of the natural product, was achieved. The key intermediate involves oxazolidine moiety...
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Stereocontrolled lithiation/trapping of chiral 2-alkylideneaziridines: investigation into the role of the aziridine nitrogen stereodynamics

Org. and Biomol. Chem. - 1 September, 2014 - 21:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01457J, PaperRENZO LUISI, Rosmara Mansueto, Leonardo Degennaro, Jean-Francois Briere, Karen Griffin, Mike Shipman, Saverio Florio
The origin of the stereoselectivity in the lithiation/trapping of 2-alkylideneaziridines bearing a chiral group as the nitrogen substituent, has been investigated. Optimal reaction conditions have been discovered by in situ...
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New Ganglio-tripod Amphiphiles (TPAs) for Membrane Protein Solubilization and Stabilization: Implications for Detergent Structure-Property Relationships

Org. and Biomol. Chem. - 1 September, 2014 - 21:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01375A, PaperPil Seok Chae, Hyoung Eun Bae, Hazrat Hussain, Muhammad Ehsan, Jin Woong Kim
Detergents are widely used for membrane protein research; however, membrane proteins encapsulated in micelles formed by conventional detergents tend to undergo structural degradation, necessitating the development of new agents with...
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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

Org. and Biomol. Chem. - 1 September, 2014 - 21:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01143K, PaperDavid Parker, Martina Delbianco, Laurent Lamarque
The synthesis is described of a series of meta and para-substituted phenylsulfonic acid derivatives of very bright Eu(III) complexes with arylphosphinate groups and strongly absorbing arylalkynylpyridine moieties. The synthetic route...
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Zinc mediated activation of terminal alkynes: stereoselective synthesis of alkynyl glycosides

Org. and Biomol. Chem. - 1 September, 2014 - 21:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01405G, CommunicationTatina Madhubabu, Anil Kumar Kusunuru, syed khalid Yousuf, debaraj mukherjee
Zinc mediated alkynylation reaction was studied for the preparation of C-glycosides from unactivated alkynes. Different glycosyl donors such as glycals and anomeric acetates were tested towards alkynyl zinc reagent obtained...
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Pd(II)-Catalyzed Ligand Controlled Synthesis of Pyrazole-4-carboxylates and Benzo[b]thiophene-3-carboxylates

Org. and Biomol. Chem. - 1 September, 2014 - 21:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01576B, PaperYogesh Daulat Dhage, Hiroki Daimon, Cheng Peng, Taichi Kusakabe, Keisuke Takahashi, Yuichro Kanno, Yoshio Inouye, Keisuke Kato
Cyclization-carbonylation of [small alpha],[small beta]-Alkynic hydrazones and (o-alkynylphenyl) (methoxymethyl) sulfides with Pd(tfa)2 in DMSO / MeOH afforded methyl pyrazole-4-carboxylates and benzo[b]thiophene-3-carboxylates, respectively, in good yields. A simple change of ligand (solvent) allowed...
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