Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Palladium mediated intramolecular multiple C-X/C-H cross coupling and C-H activation: synthesis of carbazole alkaloids calothrixin B and murrayaquinone A

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,6105-6113
DOI: 10.1039/C4OB00493K, PaperSrinivasan A. Kaliyaperumal, Shyamapada Banerjee, Syam Kumar U. K.
Straightforward palladium mediated syntheses of calothrixin B and murrayaquinone A are described.
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Mercaptobenzoic acid-palladium(0) complexes as active catalysts for S-benzylation with benzylic alcohols via ([small eta]3-benzyl)palladium(II) cations in water

27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,5964-5972
DOI: 10.1039/C4OB00688G, PaperHidemasa Hikawa, Isao Azumaya
Mercaptobenzoic acid-palladium(0) complexes show high catalytic activity for S-benzylation with benzylic alcohols via the ([small eta]3-benzyl)palladium(II) cation in water. The catalytic system can be performed using only 2.5 mol% Pd2(dba)3 without the phosphine ligand or other additives.
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Palladium-catalyzed synthesis of isoindoloquinazolinones via dicarbonylation of 1,2-dibromoarenes

27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,5835-5838
DOI: 10.1039/C4OB01103A, CommunicationJianbin Chen, Helfried Neumann, Matthias Beller, Xiao-Feng Wu
The first example of palladium-catalyzed carbonylative synthesis of isoindoloquinazolinones has been developed. Using 1,2-dibromobenzenes and 2-aminobenzyl amine as substrates, the products were isolated in moderate to good yields with the installation of two molecules of CO.
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Pyridine-phosphinimine ligand-accelerated Cu(I)-catalyzed azide-alkyne cycloaddition for preparation of 1-(pyridin-2-yl)-1,2,3-triazole derivatives

27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,5954-5963
DOI: 10.1039/C4OB01176G, PaperRanfeng Sun, Huangdong Wang, Jianfeng Hu, Jiudong Zhao, Hao Zhang
A new phosphinimine ligand was used in the Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction of tetrazolo[1,5-a]pyridines (not active in traditional CuAAC reactions) and alkynes for the first time and a series of 1-(pyridin-2-yl)-1,2,3-triazole derivatives were prepared.
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Monitoring and inhibition of Plk1: amphiphilic porphyrin conjugated Plk1 specific peptides for its imaging and anti-tumor function

27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,5876-5882
DOI: 10.1039/C4OB00853G, PaperHongguang Li, Chi-Fai Chan, Wai-Lun Chan, Sam Lear, Steven L. Cobb, Nai-Ki Mak, Terrence Chi-Kong Lau, Rongfeng Lan, Wai-Kwok Wong, Ka-Leung Wong
Polo-like kinase 1 (Plk1) is well-known for taking part in cell cycle progression and regulation.
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One-pot synthesis of polysubstituted 3-acylpyrroles by cooperative catalysis

27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,5822-5826
DOI: 10.1039/C4OB01019A, CommunicationHai-Lei Cui, Fujie Tanaka
Polysubstituted 3-acylpyrroles were synthesized from readily available unsaturated ketones and N-substituted propargylated amines via an aza-Michael/alkyne carbocyclization cascade followed by oxidation in one pot.
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An unnatural amino acid based fluorescent probe for phenylalanine ammonia lyase

27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,5818-5821
DOI: 10.1039/C4OB00914B, CommunicationZhenlin Tian, Weiping Zhu, Yufang Xu, Xuhong Qian
An unnatural amino acid based fluorescent probe 2a-LP was designed and synthesized. 2a-LP exhibited an excellent response to phenylalanine ammonia lyase both in Tris-HCl buffer and tomato samples, and was used as an intracellular sensor for phenylalanine ammonia lyase imaging.
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New multi-target-directed small molecules against Alzheimer's disease: a combination of resveratrol and clioquinol

27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,5936-5944
DOI: 10.1039/C4OB00998C, PaperFei Mao, Jun Yan, Jianheng Li, Xian Jia, Hui Miao, Yang Sun, Ling Huang, Xingshu Li
Compound 10c exhibited excellent MTDL properties: excellent abilities to moderate A[small beta] aggregation, potential antioxidant behaviour and biometal chelation.
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Rapid discovery of potent [small alpha]-fucosidase inhibitors by in situ screening of a library of (pyrrolidin-2-yl)triazoles

27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,5898-5904
DOI: 10.1039/C4OB00931B, PaperPilar Elias-Rodriguez, Elena Moreno-Clavijo, Ana T. Carmona, Antonio J. Moreno-Vargas, Inmaculada Robina
The fucosidase inhibitory activity of a library of (pyrrolidin-2-yl)triazoles generated by CuAAC can be in situ analyzed, avoiding tedious purification steps. A potent and selective inhibitor was identified.
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Palladium-catalyzed ortho-functionalization of azoarenes with aryl acylperoxides

25 July, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,5866-5875
DOI: 10.1039/C4OB00993B, PaperCheng Qian, Dongen Lin, Yuanfu Deng, Xiao-Qi Zhang, Huanfeng Jiang, Guang Miao, Xihao Tang, Wei Zeng
With the aid of an azo directing group, a Pd-catalyzed ortho-sp2 C-H bond activation/functionalization of azoarenes with aryl acyl peroxides has been explored. This transformation provides convenient access to regioselectively introducing acyloxyl and aryl group onto azoarenes.
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Synthesis and evaluation of the anticancer activity of albiziabioside A and its analogues as apoptosis inducers against human melanoma cells

25 July, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,5928-5935
DOI: 10.1039/C4OB00874J, PaperGaofei Wei, Shuai Wang, Shanshan Cui, Jia Guo, Yongxiang Liu, Yang Liu, Maosheng Cheng
We have efficiently synthesized albiziabioside A (1) together with its six disaccharide analogues and evaluated their cytotoxicity against six different skin cancer cells. The results provide for the first time a basic mechanism for the anticancer activity of 1.
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Electrochemical behaviour of new dimeric esters and amides derived from caffeic acid in dimethylsulfoxide

25 July, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,5981-5989
DOI: 10.1039/C4OB00823E, PaperAnalilia Sanchez, Omar Martinez-Mora, Evelin Martinez-Benavidez, Javier Hernandez, Zaira Dominguez, Magali Salas-Reyes
Small differences in the connectors of four new dimeric derivatives of caffeic acid exert interesting changes on their electrochemical behaviour.
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Synthesis of 4-alkynylquinazolines: Pd-Cu-cocatalyzed coupling of quinazoline-4-tosylates with terminal alkynes using N-heterocyclic carbenes as ligands

25 July, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,5922-5927
DOI: 10.1039/C4OB00700J, PaperYiyuan Peng, Ping Huang, Yu Wang, Yirong Zhou, Jianjun Yuan, Qin Yang, Xin Jiang, Zhihong Deng, Jingshi Xu
A Pd-Cu-cocatalyzed coupling reaction of quinazoline-4-tosylates with terminal alkynes using N-heterocyclic carbenes (NHC) as ligands is described.
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Tandem metal relay catalysis: from cyclopropene to polysubstituted furan

23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,5802-5806
DOI: 10.1039/C4OB00987H, PerspectiveChuanling Song, Jianwu Wang, Zhenghu Xu
Transmetalation is a key step in traditional coupling reactions. An efficient synthetic methodology of tetrasubstituted furans from cyclopropenes with Cu-Pd transmetalation relay catalysis was presented.
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Synthesis of 4-methyl-N[prime or minute]-(3-alkyl-2r,6c-diarylpiperidin-4-ylidene)-1,2,3-thiadiazole-5-carbohydrazides with antioxidant, antitumor and antimicrobial activities

23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,5911-5921
DOI: 10.1039/C4OB00739E, PaperKodisundaram Paulrasu, Arul Duraikannu, Manikandan Palrasu, Amirthaganesan Shanmugasundaram, Murugavel Kuppusamy, Balasankar Thirunavukkarasu
The structures of the newly synthesized 4-methyl-N[prime or minute]-(3-alkyl-2r,6c-diarylpiperidin-4-ylidene)-1,2,3-thiadiazole-5-carbohydrazide (5a-5l) were confirmed by spectral and elemental analysis.
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A facile route to 5-methyl-5H-indeno[1,2-c]quinolones via palladium-catalyzed cyclization of 2-alkynylbromobenzenes with N,N-dimethyl-2-alkynylanilines

23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,5861-5865
DOI: 10.1039/C4OB00706A, PaperXiaolin Pan, Yong Luo, Yunyan Kuang, Guangming Li
A tandem reaction catalyzed by palladium is developed to provide a facile and simple route for the synthesis of 5-methyl-5H-indeno[1,2-c]quinolones.
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Total synthesis of (+)-monocerin via tandem dihydroxylation-SN2 cyclization and a copper mediated tandem cyanation-lactonization approach

23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,5973-5980
DOI: 10.1039/C4OB00965G, PaperU. Nookaraju, Eeshwaraiah Begari, Pradeep Kumar
A simple and novel synthesis of (+)-monocerin was achieved from 3-buten-1-ol employing HKR, Julia olefination, intramolecular tandem Sharpless asymmetric dihydroxylation-SN2 cyclization and a novel copper mediated tandem cyanation-cyclization as the key steps.
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Theoretical study of the reaction of hydroxyl radicals with uridine: the influence of ribose and solvent

23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,5891-5897
DOI: 10.1039/C4OB00168K, PaperYa Gao, Xiayu Chen, Li Zhong, Wei Yao, Shujin Li
The reaction of [radical dot]OH with uridine has been investigated. The influence of ribose and the solvent effect are presented.
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Organocatalytic synthesis of optically active [small beta]-branched [small alpha]-amino esters via asymmetric biomimetic transamination

23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,5856-5860
DOI: 10.1039/C4OB00684D, PaperCunxiang Su, Ying Xie, Hongjie Pan, Mao Liu, Hua Tian, Yian Shi
This paper describes an efficient asymmetric biomimetic transamination of [small alpha]-keto esters with a quinine-derived chiral base as the catalyst, giving a variety of [small beta]-branched [small alpha]-amino esters in 50-96% yield and 87-95% ee.
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Asymmetric organocatalytic desymmetrization of 4,4-disubstituted cyclohexadienones at high pressure: a new powerful strategy for the synthesis of highly congested chiral cyclohexenones

23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,5847-5855
DOI: 10.1039/C4OB00733F, PaperNaomu Miyamae, Naruhisa Watanabe, Maya Moritaka, Keiji Nakano, Yoshiyasu Ichikawa, Hiyoshizo Kotsuki
A highly diastereoselective and enantioselective method for the asymmetric desymmetrization of 4,4-disubstituted cyclohexadienones at high pressure was developed.
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