Royal Society of Chemistry

TBHP-promoted sequential carboxamidation and aromatisation of aryl isonitriles with formamides

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,9257-9263
DOI: 10.1039/C4OB01850H, PaperXiaomei Feng, Hui Zhu, Lei Wang, Yan Jiang, Jiang Cheng, Jin-Tao Yu
The tert-butyl hydroperoxide (TBHP)-promoted sequential carboxamidation and aromatisation of isonitriles with formamides was developed. This reaction involved the addition of formamide radicals to isonitriles and sequential C-C bond formation by intramolecular aromatic cyclisation.
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Organocatalytic enantioselective [small alpha]-amination of 5-substituted rhodanines: an efficient approach to chiral N,S-acetals

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,9097-9100
DOI: 10.1039/C4OB01921K, CommunicationHuanrui Zhang, Baomin Wang, Longchen Cui, Ying Li, Jingping Qu, Yuming Song
A highly efficient approach to chiral N,S-acetals by asymmetric amination of 5-substituted rhodanines catalyzed by quinine or quinidine is developed.
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2-Alkynylbenzaldoxime: a versatile building block for the generation of N-heterocycles

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,9045-9053
DOI: 10.1039/C4OB01618A, Review ArticleLinman He, Hongming Nie, Guanyinsheng Qiu, Yueqiu Gao, Jie Wu
Recent advancement in the generation of N-heterocycles starting from 2-alkynylbenzaldoximes via tandem reactions is described based on different reaction types.
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Lewis acid promoted construction of chromen-4-one and isoflavone scaffolds via regio- and chemoselective domino Friedel-Crafts acylation/Allan-Robinson reaction

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,9216-9222
DOI: 10.1039/C4OB01743A, PaperTanmoy Chanda, Sushobhan Chowdhury, Suvajit Koley, Namrata Anand, Maya Shankar Singh
An efficient one-pot synthesis of chromen-4-ones and isoflavones is achieved directly from phenols via the regio- and chemoselective domino Friedel-Crafts acylation/Allan-Robinson reaction.
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The influence of the aromatic aglycon of galactoclusters on the binding of LecA: a case study with O-phenyl, S-phenyl, O-benzyl, S-benzyl, O-biphenyl and O-naphthyl aglycons

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,9166-9179
DOI: 10.1039/C4OB01599A, PaperFrancesca Casoni, Lucie Dupin, Gerard Vergoten, Albert Meyer, Caroline Ligeour, Thomas Gehin, Olivier Vidal, Eliane Souteyrand, Jean-Jacques Vasseur, Yann Chevolot, Francois Morvan
Mannose-centered galactoclusters exhibiting naphthyl or biphenyl aglycons displayed high affinity for LecA.
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Rhodium(II) catalyzed synthesis of macrocycles incorporating oxindole via O-H/N-H insertion reactions

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,9243-9256
DOI: 10.1039/C4OB01671H, PaperSengodagounder Muthusamy, Thangaraju Karikalan
Synthesis of 10- to 29-membered oxaza-macrocycles via intramolecular O-H/N-H insertion reactions catalyzed by a rhodium(II) acetate dimer is demonstrated. Synthesis of symmetric macrocycles via head to tail dimerization reactions is also delineated.
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Discovery and synthesis of a novel series of potent, selective inhibitors of the PI3K[small alpha]: 2-alkyl-chromeno[4,3-c]pyrazol-4(2H)-one derivatives

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,9157-9165
DOI: 10.1039/C4OB01589D, PaperYong Yin, Xun Wu, Hong-Wei Han, Shao Sha, She-Feng Wang, Fang Qiao, Ai-Min Lu, Peng-Cheng Lv, Hai-Liang Zhu
A series of novel 2-alkyl-chromeno[4,3-c]pyrazol-4(2H)-one derivatives were synthesized and evaluated for their biological activities. Compound 4l exhibited the most potent and selective activity for PI3K[small alpha].
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Synthesis, gelation and topochemical polymerization of meta-linked oligophenylenebutadiynylene derivatives

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,9236-9242
DOI: 10.1039/C4OB01322K, PaperIsabelle Levesque, Simon Rondeau-Gagne, Jules Romeo Neabo, Jean-Francois Morin
Rational design of meta-linked oligophenylbutadiynylene (OPBD) derivatives was conducted in order to gain insight into their gelation properties and reactivity toward topochemical polymerization to yield polydiacetylenes (PDAs).
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A theoretical study of ternary indole-cation-anion complexes

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,9145-9156
DOI: 10.1039/C4OB01879F, PaperJorge A. Carrazana-Garcia, Enrique M. Cabaleiro-Lago, Alba Campo-Cacharron, Jesus Rodriguez-Otero
The simultaneous interactions of an anion and a cation with a [small pi] system were investigated by MP2 and M06-2X theoretical calculations.
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Synthesis of substituted quinolines via allylic amination and intramolecular Heck-coupling

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,9133-9138
DOI: 10.1039/C4OB01614A, PaperSiva Murru, Brandon McGough, Radhey S. Srivastava
New catalytic approach to access substituted quinolines and naphthyridines via allylic C-H amination followed by intramolecular Heck-coupling and aerobic dehydrogenation.
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Effects of side chains on DNA binding, cell permeability, nuclear localization and cytotoxicity of 4-aminonaphthalimides

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,9207-9215
DOI: 10.1039/C4OB01274G, PaperJin Zhou, Ang Chang, Linlin Wang, Ying Liu, Xiangjun Liu, Dihua Shangguan
The guanidinoethyl group increases DNA binding, and decreases the cell permeability and cytotoxity; the dimethylaminopropyl group enhances the cell permeability and cytotoxity.
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Diversity-oriented synthesis of medicinally important 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) derivatives and higher analogs

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,9054-9091
DOI: 10.1039/C4OB01446D, Review ArticleSambasivarao Kotha, Deepak Deodhar, Priti Khedkar
This review provides an account of strategies for building diverse Tic derivatives suitable for the syntheses of medicinally important molecules.
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Frustrated Lewis pair catalyzed hydrosilylation and hydrosilane mediated hydrogenation of fulvenes

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,9139-9144
DOI: 10.1039/C4OB01346H, PaperSergej Tamke, Constantin-G. Daniliuc, Jan Paradies
The hydrosilane assisted FLP-catalyzed hydrogenation of pentafulvenes is reported.
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Towards novel efficient and stable nuclear import signals: synthesis and properties of trimethylguanosine cap analogs modified within the 5[prime or minute],5[prime or minute]-triphosphate bridge

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,9184-9199
DOI: 10.1039/C4OB01579G, PaperMalgorzata Zytek, Joanna Kowalska, Maciej Lukaszewicz, Blazej A. Wojtczak, Joanna Zuberek, Aleksandra Ferenc-Mrozek, Edward Darzynkiewicz, Anna Niedzwiecka, Jacek Jemielity
A study of methylenebisphosphonate, imidodiphosphate, phosphorothioate and boranophosphate TMG cap analogs.
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Total synthesis of macrodiolide ionophores aplasmomycin A and boromycin via double ring contraction

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,9116-9132
DOI: 10.1039/C4OB01017E, PaperMitchell A. Avery, Satish C. Choudhry, Om Prakash Dhingra, Brian D. Gray, Myung-chol Kang, Shen-chun Kuo, Thalathani R. Vedananda, James D. White, Alan J. Whittle
Aplasmomycin A was synthesized by double ring contraction of a 34-membered dilactone; boromycin was synthesized using the same strategy.
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Structural Insight into the Aggregation of L-Prolyl Dipeptides and its Effect on Organocatalytic Performance

Org. and Biomol. Chem. - 30 October, 2014 - 10:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02003K, PaperJuan F Miravet, Beatriu Escuder, Cristina Berdugo
NMR and organocatalytic studies of four dipeptides derived from L-proline are described. Results indicate that important conformational changes around the catalytic L-proline moiety are observed for free dipeptides upon changing...
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Exploiting the Narrow Gap of Rearrangement between the Substituents in the Vicinal Disubsitution Reactions of Diaryliodonium Salts with Pyridine N-sulfonamidates

Org. and Biomol. Chem. - 30 October, 2014 - 10:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01744G, PaperYong Wang, Ming Li, Li-Rong Wen, Jing Peng, Xiang Su, Chao Chen
The vicinal disubstitution reaction of diaryliodonium salts with pyridine N-sulfonamidates were fully examined to afford o-pyridinium anilines. A pathway of N-arylation occurred at the amidate group followed by a radical...
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Pd(II)-Catalyzed C-H Arylation of Aryl and Benzyl Weinreb Amides

Org. and Biomol. Chem. - 30 October, 2014 - 10:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02039A, CommunicationXi-Sheng Wang, Yan Wang, Kai Zhou, Quan Lan
The first example of palladium-catalyzed ortho-C-H arylation of aryl and benzyl Weinreb amides was developed, in which HOTf was used as a key promoter. This method exhibits good functional groups...
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Naphthalene Diimides as Red Fluorescent pH Sensors for Functional Cells Imaging

Org. and Biomol. Chem. - 30 October, 2014 - 10:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02054E, PaperFilippo Doria, Marco Folini, Vincenzo Grande, Graziella Cimino-Reale, Nadia Zaffaroni, Mauro Freccero
A small library of hydrosoluble naphthalene diimides (NDIs) was designed and synthesized, as cell permeable pH "turned-on" fluorescent sensors, for cellular applications. The NDIs exhibit a non-emitting twisted intramolecular charge...
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Synthesis and evaluation of protein arginine N-methyltransferase inhibitors designed to simultaneously occupy both substrate binding sites

Org. and Biomol. Chem. - 30 October, 2014 - 10:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01734J, PaperMatthijs van Haren, Linda Quarles van Ufford, Ed E. Moret, Nathaniel I. Martin
The protein arginine N-methyltransferases (PRMTs) are a family of enzymes that function by specifically transferring a methyl group from the cofactor S-adenosyl-L-methionine (AdoMet) to the guanidine group of arginine residues...
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