Org. and Biomol. Chem.

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A theoretical study on the mechanisms of the reactions between 1,3-dialkynes and ammonia derivatives for the formation of five-membered N-heterocycles

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01015A, PaperYang Wang, Donghui Wei, Wenjing Zhang, Yanyan Wang, Yanyan Zhu, Yu Jia, Mingsheng Tang
The reaction mechanisms between 1,3-dialkynes and ammonia derivatives for the formation of five-membered N-heterocycles have been investigated using the DFT method.
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Exploring dual electrophiles in peptide-based proteasome inhibitors: carbonyls and epoxides

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5710-5718
DOI: 10.1039/C4OB00893F, PaperBo-Tao Xin, Gerjan de Bruin, Martijn Verdoes, Dmitri V. Filippov, Gijs A. van der Marel, Herman S. Overkleeft
Peptide epoxyketones are potent and selective proteasome inhibitors.
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Selective recognition of anionic cell membranes using targeted liposomes coated with zinc(II)-bis(dipicolylamine) affinity units

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5645-5655
DOI: 10.1039/C4OB00924J, PaperSerhan Turkyilmaz, Douglas R. Rice, Rachael Palumbo, Bradley D. Smith
Liposomes containing phospholipid-PEG conjugates with terminal zinc([i without dot][i without dot])-bis(dipicolylamine) affinity units selectively target anionic membrane surfaces including the exterior of bacterial and dead/dying mammalian cells.
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Palladium-catalyzed oxidative carbonylative coupling of arylboronic acids with terminal alkynes to alkynones

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5590-5593
DOI: 10.1039/C4OB01128G, CommunicationKishore Natte, Jianbin Chen, Helfried Neumann, Matthias Beller, Xiao-Feng Wu
The first example of palladium-catalyzed oxidative carbonylation of arylboronic acids with terminal alkynes has been developed. By an appropriate combination of a palladium salt, a ligand, and an oxidant, the desired alkynones were isolated in moderate to good yields.
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Synthesis of tertiary propargylamines via a rationally designed multicomponent reaction of primary amines, formaldehyde, arylboronic acids and alkynes

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5597-5600
DOI: 10.1039/C4OB01055H, CommunicationOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Jiayi Wang, Qiaoying Shen, Pinzhen Li, Yanqing Peng, Gonghua Song
A novel approach for the synthesis of tertiary propargylamines is achieved through a Cu(OAc)2-catalyzed multicomponent reaction of primary amines, formaldehyde, arylboronic acids and alkynes.
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One-pot, two-step desymmetrization of symmetrical benzils catalyzed by the methylsulfinyl (dimsyl) anion

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5733-5744
DOI: 10.1039/C4OB00759J, PaperDaniele Ragno, Olga Bortolini, Pier Paolo Giovannini, Alessandro Massi, Salvatore Pacifico, Anna Zaghi
Symmetrical-to-unsymmetrical benzil conversion is realized by a one-pot two-step procedure involving a chemoselective cross-benzoin reaction followed by microwave-assisted oxidation of the benzoylated benzoin intermediate.
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Synthesis of quinazolines via CuO nanoparticles catalyzed aerobic oxidative coupling of aromatic alcohols and amidines

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5752-5756
DOI: 10.1039/C4OB00569D, PaperWu Zhang, Fei Guo, Fei Wang, Na Zhao, Liang Liu, Jia Li, Zhenghua Wang
Quinazoline derivatives were obtained via CuO nanoparticles catalyzed reaction of N-arylamidines and aromatic alcohols in air.
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Multivalent glycosylated nanoparticles for studying carbohydrate-protein interactions

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5563-5573
DOI: 10.1039/C4OB00827H, Review ArticleAvijit K. Adak, Hong-Jyune Lin, Chun-Cheng Lin
Glyconanoparticles decorated with multiple copies of various biologically relevant carbohydrates serve as scaffolds for protein binding assay, molecular imaging, targeted therapy, and bacterium detection.
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A general approach to the synthesis of 5-S-functionalized pyrimidine nucleosides and their analogues

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5634-5644
DOI: 10.1039/C4OB00597J, PaperDzmitry G. Kananovich, Alli Reino, Kaja Ilmarinen, Marko Roomusoks, Mati Karelson, Margus Lopp
A palladium-catalyzed C-S coupling reaction has been used as a key step for the introduction of S-functionality at the C-5 position of the cytosine and uracil nucleosides and their analogues.
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Copper-catalyzed nucleophilic trifluoromethylation of benzylic chlorides

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5594-5596
DOI: 10.1039/C4OB00957F, CommunicationYoshihiro Miyake, Shin-ichi Ota, Masashi Shibata, Kazunari Nakajima, Yoshiaki Nishibayashi
The reactions of primary and secondary benzylic chlorides with trifluoromethyltrimethylsilane in the presence of a catalytic amount of copper(I) thiophene-2-carboxylate (CuTC) have been found to give the corresponding benzylic trifluoromethylated products in good to high yields.
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A copper-mediated cross-coupling approach for the synthesis of 3-heteroaryl quinolone and related analogues

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5719-5726
DOI: 10.1039/C4OB00939H, PaperSanghye Shin, Yechan Kim, Kiho Kim, Sungwoo Hong
An efficient and practical method for the direct cross-coupling between quinolones and a range of azoles was developed via copper-mediated C-H functionalization.
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DABCO-catalyzed [3 + 2] annulation of sulfamate-derived cyclic imines with isocyanoacetates: synthesis of sulfamate-fused 2-imidazoline

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5691-5697
DOI: 10.1039/C4OB00840E, PaperZhenzhen Gao, Lei Zhang, Zhanhu Sun, Hao Yu, Yumei Xiao, Hongchao Guo
A novel DABCO-catalyzed [3 + 2] annulation of sulfamate-derived cyclic imines with isocyanoacetates.
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One-pot synthesis of 2-amino-4(3H)-quinazolinones via ring-opening of isatoic anhydride and palladium-catalyzed oxidative isocyanide-insertion

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5766-5772
DOI: 10.1039/C4OB00484A, PaperFei Ji, Mei-Fang Lv, Wen-Bin Yi, Chun Cai
An efficient and practical two-step process has been developed for the synthesis of 2-amino-4(3H)-quinazolinones via ring-opening of isatoic anhydride and palladium-catalyzed oxidative isocyanide-insertion in one pot.
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Synthesis and chemosensory application of water-soluble polyfluorenes containing carboxylated groups

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5682-5690
DOI: 10.1039/C4OB00944D, PaperChia-Shing Wu, Hsiao-Chu Su, Yun Chen
A water-soluble polyfluorene containing carboxylated groups (P1), prepared via the hydrolysis of poly[9,9[prime or minute]-bis(tert-butyl-3[prime or minute][prime or minute]-propanoate)fluoren-2,7-yl] (P0), shows high selectivity and sensitivity toward Cu+ and Cu2+, with the Stern-Volmer constants (Ksv) being 3.5 [times] 106 and 5.78 [times] 106 M-1, respectively.
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A DFT-based model for calculating solvolytic reactivity. The nucleofugality of aliphatic carboxylates in terms of Nf parameters

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5698-5709
DOI: 10.1039/C4OB00563E, PaperBernard Denegri, Mirela Matic, Olga Kronja
The proposed model reaction affords heterolytic reactivities of carboxylates that correlate well with the corresponding experimental data, enabling the use of DFT methods in estimating solvolytic reactivities of carboxylates.
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Efficient synthesis of mibefradil analogues: an insight into in vitro stability

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5669-5681
DOI: 10.1039/C4OB00504J, PaperJi Eun Lee, Tae Hui Kwon, Su Jin Gu, Duck-Hyung Lee, B. Moon Kim, Jae Yeol Lee, Jae Kyun Lee, Seon Hee Seo, Ae Nim Pae, Gyochang Keum, Yong Seo Cho, Sun-Joon Min
New mibefradil analogues were synthesized by a diastereoselective intramolecular carbonyl-ene reaction as a key transformation. The structural modification of mibefradil significantly reduced CYP inhibition and microsomal degradation.
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Strategies for desymmetrising trehalose to synthesise trehalose glycolipids

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5558-5562
DOI: 10.1039/C4OB00587B, PerspectiveChia-Hui Wu, Cheng-Chung Wang
The desymmetrisation and regioselective protection of trehalose are major challenges in the chemical synthesis of biologically essential trehalose glycolipids.
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Chemoselective reduction and self-immolation based FRET probes for detecting hydrogen sulfide in solution and in cells

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5629-5633
DOI: 10.1039/C4OB00923A, PaperBifeng Chen, Peng Wang, Qingqing Jin, Xinjing Tang
A general approach in designing H2S fluorescent probes based on FRET and self-immolative linkers.
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Total synthesis of gonytolides C and G, lachnone C, and formal synthesis of blennolide C and diversonol

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5601-5610
DOI: 10.1039/C4OB00950A, PaperGangarajula Sudhakar, Shruthi Bayya, Vilas D. Kadam, Jagadeesh Babu Nanubolu
The total syntheses of gonytolide C and related compounds have been accomplished from the aldol reaction between acetophenone derived from orcinol and butyrolactone containing ketone, followed by the diastereoselective intramolecular cyclization.
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Iron-catalyzed radical aryldifluoromethylation of activated alkenes to difluoromethylated oxindoles

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5582-5585
DOI: 10.1039/C4OB00758A, CommunicationJian-Yong Wang, Xin Zhang, Yan Bao, Yue-Ming Xu, Xiu-Fen Cheng, Xi-Sheng Wang
An iron-catalyzed aryldifluoromethylation of activated alkenes has been developed, which is a rare example where a cosolvent is used to improve the yield along with Fenton's reagent.
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