Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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De novo synthesis of phenolic dihydroxanthene near-infrared emitting fluorophores

30 July, 2015 - 06:17

Org. Biomol. Chem., 2015, 13,8169-8172
DOI: 10.1039/C5OB01223F, CommunicationJean-Alexandre Richard
We report a flexible de novo synthesis of phenolic dihydroxanthenes in 60-70% yield thanks to a one-pot cascade sequence.
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Unified mild reaction conditions for C2-selective Pd-catalysed tryptophan arylation, including tryptophan-containing peptides

30 July, 2015 - 06:17

Org. Biomol. Chem., 2015, 13,8298-8309
DOI: 10.1039/C5OB01174D, PaperAlan J. Reay, Thomas J. Williams, Ian J. S. Fairlamb
Mild Pd-mediated C-H functionalisation protocols, facilitating tryptophan C2-arylation, have been developed. Tryptophan-containing peptides, susceptible to oxidation, have been arylated.
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An atom-economic approach to carboxylic acids via Pd-catalyzed direct addition of formic acid to olefins with acetic anhydride as a co-catalyst

30 July, 2015 - 06:17

Org. Biomol. Chem., 2015, 13,8416-8419
DOI: 10.1039/C5OB01180A, CommunicationYang Wang, Wenlong Ren, Yian Shi
An effective Pd-catalyzed hydrocarboxylation of olefins using formic acid with acetic anhydride as a co-catalyst is described.
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Copper-catalyzed trifluoromethylation of alkenes: synthesis of trifluoromethylated benzoxazines

30 July, 2015 - 06:17

Org. Biomol. Chem., 2015, 13,8411-8415
DOI: 10.1039/C5OB01196E, CommunicationSadhan Jana, Athira Ashokan, Shailesh Kumar, Ajay Verma, Sangit Kumar
A ligand and base free copper catalyzed method has been developed for the construction of trifluoromethylated benzoxazines by using Umemoto's reagent.
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Oligoethylene glycol-substituted aza-BODIPY dyes as red emitting ER-probes

30 July, 2015 - 06:17

Org. Biomol. Chem., 2015, 13,8271-8276
DOI: 10.1039/C5OB01104C, PaperAnyanee Kamkaew, Sopida Thavornpradit, Thamon Puangsamlee, Dongyue Xin, Nantanit Wanichacheva, Kevin Burgess
This study features aza-BODIPY (BF2-chelated azadipyrromethene) dyes with two aromatic substituents linked by oligoethylene glycol fragments to increase hydrophilicity of aza-BODIPY for applications in intracellular imaging.
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Mechanistic insight into conjugated N-N bond cleavage by Rh(III)-catalyzed redox-neutral C-H activation of pyrazolones

30 July, 2015 - 06:17

Org. Biomol. Chem., 2015, 13,8251-8260
DOI: 10.1039/C5OB00977D, PaperWeirong Wu, Yuxia Liu, Siwei Bi
DFT calculations are performed to understand the conjugated N-N bond cleavage by Rh(III)-catalyzed redox-neutral C-H activation of pyrazolones with PhC[triple bond, length as m-dash]CPh.
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A theoretical investigation of substituent effects on the stability and reactivity of N-heterocyclic olefin carboxylates

30 July, 2015 - 06:17

Org. Biomol. Chem., 2015, 13,8533-8544
DOI: 10.1039/C5OB01021G, PaperLiang Dong, Jun Wen, Weiyi Li
Introduction of four phenyl groups at C-position and N-position not only favors decarboxylation but also ensures NHO as a strong nucleophile.
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Formation and aromatization of strained bicyclic pyrazolidines via tandem reaction of alkyl 2-aroyl-1-chlorocyclopropanecarboxylates with acylhydrazones

30 July, 2015 - 06:17

Org. Biomol. Chem., 2015, 13,8561-8566
DOI: 10.1039/C5OB01199J, PaperZhimei Huang, Junhao Hu, Yuefa Gong
The formation and aromatization of strained bicyclic pyrazolidines.
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Efficient routes towards a series of 5,5[prime or minute]-bithiazolidinylidenes as [small pi]-electron acceptors

30 July, 2015 - 06:17

Org. Biomol. Chem., 2015, 13,8479-8486
DOI: 10.1039/C5OB01169H, PaperY. Le Gal, D. Ameline, N. Bellec, A. Vacher, T. Roisnel, V. Dorcet, O. Jeannin, D. Lorcy
Among different approaches, the thermal treatment of the fused bicycle involving a dithiole-2-one ring is the most efficient one and opens access to a variety of [small pi]-conjugated electron acceptors.
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Cu(OAc)2-promoted reaction of [60]fullerene with primary amines or diamines

30 July, 2015 - 06:17

Org. Biomol. Chem., 2015, 13,8405-8410
DOI: 10.1039/C5OB01048A, CommunicationXin-Wei Lu, Meng-Lei Xing, Chun-Bao Miao, Jia-Xing Li, Xiao-Qiang Sun, Hai-Tao Yang
The Cu(OAc)2-mediated oxidative dehydrogenative addition of easily available primary amines to C60 allows the concise preparation of aziridinofullerenes. Moreover, the Cu(OAc)2-promoted reaction of C60 with diamines affords C60-fused cyclic 1,2-diaminated fullerenes.
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The first proton sponge-based amino acids: synthesis, acid-base properties and some reactivity

30 July, 2015 - 06:17

Org. Biomol. Chem., 2015, 13,8524-8532
DOI: 10.1039/C5OB01065A, PaperValery A. Ozeryanskii, Anastasia Yu. Gorbacheva, Alexander F. Pozharskii, Marina P. Vlasenko, Alexander Yu. Tereznikov, Margarita S. Chernov'yants
The first hybrid bases constructed from 1,8-bis(dimethylamino)naphthalene and glycine or alanine residues were synthesised and structurally characterised and unusual channels of their reactivity revealed.
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Leishmania cell wall as a potent target for antiparasitic drugs. A focus on the glycoconjugates

30 July, 2015 - 06:17

Org. Biomol. Chem., 2015, 13,8393-8404
DOI: 10.1039/C5OB00563A, Review ArticleYari Cabezas, Laurent Legentil, Florence Robert-Gangneux, Franck Daligault, Sorya Belaz, Caroline Nugier-Chauvin, Sylvain Tranchimand, Charles Tellier, Jean-Pierre Gangneux, Vincent Ferrieres
The basic structure of membrane glycoconjugates in Leishmania still inspires therapeutic drugs fighting against this parasite.
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Cyclic acetals as cleavable linkers for affinity capture

30 July, 2015 - 06:17

Org. Biomol. Chem., 2015, 13,8445-8452
DOI: 10.1039/C5OB01056J, PaperSiyeon Lee, Wei Wang, Younjoo Lee, Nicole S. Sampson
A cyclic acetal moiety is an acid-sensitive linker for affinity capture and which provides an aldehyde for further elaboration.
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Multicomponent domino reactions of hydrazinecarbodithioates: concise access to 3-substituted 5-thiol-1,3,4-thiadiazolines

30 July, 2015 - 06:17

Org. Biomol. Chem., 2015, 13,8177-8181
DOI: 10.1039/C5OB01166C, CommunicationHuihui Jia, Huangdi Feng, Zhihua Sun
Two classes of addition/cycloaddition cascade reactions of hydrazinecarbodithioate (1) have been developed under mild reaction conditions.
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Divergent synthesis of various iminocyclitols from D-ribose

30 July, 2015 - 06:17

Org. Biomol. Chem., 2015, 13,8512-8523
DOI: 10.1039/C5OB01042J, PaperRamu Petakamsetty, Vipin Kumar Jain, Pankaj Kumar Majhi, Ramesh Ramapanicker
A very efficient route to the diastereoselective synthesis of polyhydroxy pyrrolidines, piperidines and azepanes from an aldehyde derivative of ribose is reported.
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Natural nitric oxide (NO) inhibitors from the rhizomes of Curcuma phaeocaulis

30 July, 2015 - 06:17

Org. Biomol. Chem., 2015, 13,8349-8358
DOI: 10.1039/C5OB00964B, PaperJiang-Hao Ma, Feng Zhao, Ying Wang, Yue Liu, Su-Yu Gao, Li-Qin Ding, Li-Xia Chen, Feng Qiu
Four new sesquiterpenes, two nor-sesquiterpenes including a new skeleton, one cyclic diarylheptanoid, and one aromatic acid were isolated from Curcuma phaeocaulis.
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A quantum chemical study of the [small omega]-transaminase reaction mechanism

30 July, 2015 - 06:17

Org. Biomol. Chem., 2015, 13,8453-8464
DOI: 10.1039/C5OB00690B, PaperKarim Engelmark Cassimjee, Bianca Manta, Fahmi Himo
The detailed half-transamination mechanism of Chromobacterium violaceum [small omega]-transaminase is investigated by means of density functional theory calculations.
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Mixed behavior of p-phenylenediaminium guest binding with the inverted cucurbit[6]uril host

30 July, 2015 - 06:17

Org. Biomol. Chem., 2015, 13,8330-8334
DOI: 10.1039/C5OB01074H, PaperDe-Qing Zhang, Rui-Lian Lin, Wen-Qi Sun, Zhu Tao, Qian-Jian Zhu, Jing-Xin Liu
The binding interaction between inverted cucurbit[6]uril (iQ[6]) and p-phenylenediaminium has been investigated by X-ray crystallography, 1H NMR spectroscopy and ITC. Our data indicate that the host and the guest can form two different types of complexes: one is an inclusion structure and the other is a sandwich structure.
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Copper-mediated cyanation of indoles and electron-rich arenes using DMF as a single surrogate

30 July, 2015 - 06:17

Org. Biomol. Chem., 2015, 13,8322-8329
DOI: 10.1039/C5OB01244A, PaperLianpeng Zhang, Ping Lu, Yanguang Wang
The copper-mediated cyanation of indoles with DMF as a single surrogate of "CN" has been realized.
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Concise diastereoselective synthesis of calcaripeptide C via asymmetric transfer hydrogenation/Pd-induced chiral allenylzinc as a key reaction

30 July, 2015 - 06:17

Org. Biomol. Chem., 2015, 13,8487-8494
DOI: 10.1039/C5OB01164G, PaperGullapalli Kumaraswamy, Vykunthapu Narayanarao, Ragam Raju
The synthesis of the cyclodepsipeptide calcaripeptide C was accomplished with an overall yield of 10.7% by a catalytic asymmetric transfer hydrogenation (ATH) together with Marshall's allenylation as pivotal reactions.
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