Org. and Biomol. Chem.

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Facile access to amides and hydroxamic acids directly from nitroarenes

10 August, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,6465-6469
DOI: 10.1039/C4OB01155D, PaperShreyans K. Jain, K. A. Aravinda Kumar, Sandip B. Bharate, Ram A. Vishwakarma
Herein, we report a new method for synthesis of amides and hydroxamic acids directly from nitroarenes and aldehydes.
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Synthesis and properties of oligonucleotides modified with 2[prime or minute]-O-(2-carboxyethyl)nucleotides and their carbamoyl derivatives

10 August, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,6457-6464
DOI: 10.1039/C4OB01260G, PaperTakeshi Yamada, Yoshiaki Masaki, Natsuki Okaniwa, Takashi Kanamori, Akihiro Ohkubo, Hirosuke Tsunoda, Kohji Seio, Mitsuo Sekine
2[prime or minute]-O-Methyl oligoribonucleotides with four kinds of 2[prime or minute]-O-modified uridine derivatives were synthesised.
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Multicomponent reaction of chalcones, malononitrile and DMF leading to [gamma]-ketoamides

10 August, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,6389-6392
DOI: 10.1039/C4OB00971A, PaperEnxiang Wei, Bing Liu, Shaoxia Lin, Fushun Liang
An efficient synthesis of [gamma]-ketoamides was developed by the one-pot multicomponent reaction of chalcones, malononitrile and DMF (as both the reactant and solvent) in the presence of NaOH (3.0 equiv.). The reaction features high atom economy, easily available starting materials, operational simplicity, and good tolerance with diverse functional groups.
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Tautomerisation of thymine acts against the Huckel 4N + 2 rule. The effect of metal ions and H-bond complexations on the electronic structure of thymine

10 August, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,6476-6483
DOI: 10.1039/C4OB00964A, PaperOlga A. Stasyuk, Halina Szatylowicz, Tadeusz M. Krygowski
Not necessarily the [small pi]-electron delocalization is responsible for the stability of thymine tautomers.
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Rational design of a new fluorescent 'ON/OFF' xanthene dye for phosphate detection in live cells

10 August, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,6432-6439
DOI: 10.1039/C4OB00951G, PaperA. Martinez-Peragon, D. Miguel, A. Orte, A. J. Mota, M. J. Ruedas-Rama, J. Justicia, J. M. Alvarez-Pez, J. M. Cuerva, L. Crovetto
A new fluorescein derivative with ON/OFF features, 9-[1-(4-tert-butyl-2-methoxyphenyl)]-6-hydroxy-3H-xanthen-3-one (Granada Green, GG), was designed and synthesised.
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An efficient, Schiff-base derivative for selective fluorescence sensing of Zn2+ ions: quantum chemical calculation appended by real sample application and cell imaging study

8 August, 2014 - 14:17

Org. Biomol. Chem., 2014, 12,6447-6456
DOI: 10.1039/C4OB00732H, PaperSayantani Chall, Soumya Sundar Mati, Saugata Konar, Dipti Singharoy, Subhash Chandra Bhattacharya
Fluorescence based sensitive detection of the second most abundant metal ion (Zn2+) was established using a newly synthesized Schiff-base ligand, PyHP.
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Enantioselective synthesis of [small alpha],[small alpha]-difluoro-[small beta]-lactams using amino alcohol ligands

8 August, 2014 - 14:17

Org. Biomol. Chem., 2014, 12,6484-6489
DOI: 10.1039/C4OB01184H, PaperAtsushi Tarui, Takeshi Ikebata, Kazuyuki Sato, Masaaki Omote, Akira Ando
A practical and highly enantioselective Reformatsky reaction of ethyl bromodifluoroacetate with imines using a cheap and commercially available amino alcohol ligand is described.
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Enantioselective synthesis of [gamma]-tetrasubstituted nitrosulfonyl carboxylates and amides viaL-tert-leucine-derived-squaramide catalyzed conjugate addition of nitrosulfones to acrylates and acrylamides

8 August, 2014 - 14:17

Org. Biomol. Chem., 2014, 12,6425-6431
DOI: 10.1039/C4OB00344F, PaperKalisankar Bera, Irishi N. N. Namboothiri
A t-leucine-derived squaramide catalyzed reaction of [small alpha]-nitrosulfones with acrylates/acrylamides provides [gamma]-tetrasubstituted [gamma]-nitro-[gamma]-sulfonyl carboxylates/amides in excellent yield and enantioselectivity.
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Electrochemical and theoretical analysis of the reactivity of shikonin derivatives: dissociative electron transfer in esterified compounds

6 August, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,6393-6398
DOI: 10.1039/C4OB01207K, PaperGeorgina Armendariz-Vidales, Carlos Frontana
Electrochemical and theoretical analysis of Shikonin derivatives revealed that for esterified compounds, a dissociative electron transfer process occurs.
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An unusual mulinane diterpenoid from the Chilean plant Azorella trifurcata (Gaertn) Pers

6 August, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,6406-6413
DOI: 10.1039/C4OB00966E, PaperCarlos Areche, Beatriz Sepulveda, Aurelio San Martin, Olimpo Garcia-Beltran, Mario Simirgiotis, Alvaro Canete
An unusual mulinane diterpenoid named 7[small alpha]-acetoxy-9-epi-13[small beta]-hydroxymulinane was isolated from A. trifurcate. This compound possesses a new trans-syn-trans arrangement in a tricyclic ring system not previously encountered in nature.
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Efficient asymmetric synthesis of N-protected-[small beta]-aryloxyamino acids via regioselective ring opening of serine sulfamidate carboxylic acid

6 August, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,6507-6515
DOI: 10.1039/C4OB01047G, PaperRajesh Malhotra, Tushar K. Dey, Swarup Dutta, Sourav Basu, Saumen Hajra
First regioselective ring opening of serine derived cyclic sulfamidate with ArONa is developed to provide an easy and direct access of a variety of N-Boc- and N-PMB protected [small beta]-aryloxy-[small alpha]-amino acids with complete retention of enantiopurity in moderate to high yields.
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Amino acid chirons: a tool for asymmetric synthesis of heterocycles

6 August, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,6297-6339
DOI: 10.1039/C4OB00943F, Review ArticlePriyanka Singh, Krishnananda Samanta, Sanjit Kumar Das, Gautam Panda
This review describes diverse asymmetric heterocycles with various membered rings (n = 3-9) for the period from 1996 to Dec. 2013.
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Aliphatic amine responsive organogel system based on a simple naphthalimide derivative

6 August, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,6399-6405
DOI: 10.1039/C4OB00728J, PaperXinhua Cao, Tingting Zhang, Aiping Gao, Keli Li, Qiuli Cheng, Lijuan Song, Min Zhang
Aliphatic amines and aromatic amines were distinguished and detected by an organogel system containing naphthalimide.
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A hydrophobic disordered peptide spontaneously anchors a covalently bound RNA hairpin to giant lipidic vesicles

6 August, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,6363-6373
DOI: 10.1039/C4OB00721B, PaperAlexandra Le Chevalier Isaad, Paolo Carrara, Pasquale Stano, Kollappillil S. Krishnakumar, Dominique Lafont, Alexandra Zamboulis, Rene Buchet, Denis Bouchu, Florian Albrieux, Peter Strazewski
Exergonic compartmentation of nucleic acids to liposomes through conjugation with peptides lends experimental support to early evolvable RNA-peptide 'collaboration'.
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Asymmetric synthesis of substituted NH-piperidines from chiral amines

6 August, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,6384-6388
DOI: 10.1039/C4OB00657G, PaperLekh Nath Gautam, Yijin Su, Novruz G. Akhmedov, Jeffrey L. Petersen, Xiaodong Shi
Previously, we reported an efficient asymmetric synthesis of substituted piperidines through an exocyclic chirality induced nitroalkene/amine/enone (NAE) condensation reaction.
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DFT study on the reaction mechanisms and stereoselectivities of NHC-catalyzed [2 + 2] cycloaddition between arylalkylketenes and electron-deficient benzaldehydes

6 August, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,6374-6383
DOI: 10.1039/C4OB00606B, PaperMengmeng Zhang, Donghui Wei, Yang Wang, Suiji Li, Jiefei Liu, Yanyan Zhu, Mingsheng Tang
Two possible mechanisms of ketene and aldehyde [2 + 2] cycloaddition catalyzed by NHC have been investigated using the DFT method.
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Relative contractile motion of the rings in a switchable palindromic [3]rotaxane in aqueous solution driven by radical-pairing interactions

4 August, 2014 - 13:17

Org. Biomol. Chem., 2014, 12,6089-6093
DOI: 10.1039/C4OB01228C, CommunicationLeah S. Witus, Karel J. Hartlieb, Yuping Wang, Aleksandrs Prokofjevs, Marco Frasconi, Jonathan C. Barnes, Edward J. Dale, Albert C. Fahrenbach, J. Fraser Stoddart
This communication describes a mechanically interlocked molecule (MIM), capable of switchable and reversible linear molecular motion.
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1,1,1,3,3,3-Hexafluoro-2-propanol and 2,2,2-trifluoroethanol solvents induce self-assembly with different surface morphology in an aromatic dipeptide

2 August, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,6181-6189
DOI: 10.1039/C4OB00821A, PaperSamala Murali Mohan Reddy, Ganesh Shanmugam, Asit Baran Mandal
1,1,1,3,3,3-Hexafluoro-2-propanol and 2,2,2-trifluoroethanol solvents, which are known to disaggregate self-assembled peptides, induce the self-assembly of aromatic dipeptides to give structures with different surface morphologies.
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Total synthesis of fluoxetine and duloxetine through an in situ imine formation/borylation/transimination and reduction approach

2 August, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,6121-6127
DOI: 10.1039/C4OB01142B, PaperAdam D. J. Calow, Elena Fernandez, Andrew Whiting
Efficient, catalytic, asymmetric total syntheses of both (R)-fluoxetine and (S)-duloxetine from [small alpha],[small beta]-unsaturated aldehydes are reported.
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A fluorescent probe for intracellular cysteine overcoming the interference by glutathione

2 August, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,6128-6133
DOI: 10.1039/C4OB00382A, PaperMinggang Tian, Fuqiang Guo, Yuming Sun, Weijia Zhang, Fang Miao, Yong Liu, Guofen Song, Cheuk-Lam Ho, Xiaoqiang Yu, Jing Zhi Sun, Wai-Yeung Wong
A fluorescent probe was reported to discriminate 30-200 [small mu ]M cysteine, overcoming the interference by 1-10 mM glutathione. The selectivity was also proved by cellular experiments.
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