Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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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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Palladium-catalyzed microwave-assisted direct arylation of imidazo[2,1-b]thiazoles with aryl bromides: synthesis and mechanistic study

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5773-5780
DOI: 10.1039/C4OB00600C, PaperYi-Shuo Zhu, Benyi Shi, Ran Fang, Xiaoxuan Wang, Huanwang Jing
A palladium-catalyzed regioselective C-H arylation of imidazo[2,1-b]thiazoles under microwave irradiation via a concerted metalation-deprotonation (CMD) pathway was developed.
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Elucidating factors leading to acidolytic degradation of sterically strained oligoether dendrons

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5621-5628
DOI: 10.1039/C4OB00540F, PaperJ. Karabline-Kuks, A. Fallek, M. Portnoy
Monitoring of the disassembly of third-generation sterically crowded oligoether dendrons in acidic solution reveals their exact degradation sequence, synergistically induced by electron donation and steric strain.
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Synthesis of functionalized chromones through sequential reactions in aqueous media

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5757-5765
DOI: 10.1039/C4OB00618F, PaperSaber Mehrparvar, Saeed Balalaie, Mahnaz Rabbanizadeh, Frank Rominger, Elmira Ghabraie
An efficient synthesis protocol has been developed for diversity-oriented functionalized compounds via four-component reaction of chromone carbaldehydes, Meldrum's acid, 4-hydroxyl coumarin or 6-methyl-4-hydroxyl-pyrone and primary alcohols in aqueous media.
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Pd(OAc)2/DABCO as an efficient and phosphine-free catalytic system for the synthesis of single and double Weinreb amides by the aminocarbonylation of aryl iodides

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5727-5732
DOI: 10.1039/C4OB00729H, PaperSandip T. Gadge, Bhalchandra M. Bhanage
Single and double Weinreb amides were synthesized using a Pd(OAc)2 catalyst and DABCO as an inexpensive and stable ligand using carbonylation methodology under phosphine-free conditions.
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Electrophilicity and nucleophilicity of commonly used aldehydes

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5781-5788
DOI: 10.1039/C4OB00555D, PaperSanjay Pratihar
The present approach for determining the electrophilicity (E) and nucleophilicity (N) of aldehydes includes a kinetic study of KMNO4 oxidation and NaBH4 reduction of aldehydes.
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Hydroxyl radical induced oxidation of theophylline in water: a kinetic and mechanistic study

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5611-5620
DOI: 10.1039/C4OB00102H, PaperM. M. Sunil Paul, U. K. Aravind, G. Pramod, A. Saha, C. T. Aravindakumar
Evidence is reported for the addition and hydrogen abstraction reactions of hydroxyl radicals with an important pharmaceutically active compound, theophylline.
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Efficient palladium-catalyzed double carbonylation of o-dibromobenzenes: synthesis of thalidomide

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5578-5581
DOI: 10.1039/C4OB00796D, CommunicationJianbin Chen, Kishore Natte, Anke Spannenberg, Helfried Neumann, Matthias Beller, Xiao-Feng Wu
A convenient and mild procedure for double carbonylation of o-dibromobenzene with various 2-amino pyridines and naturally occurring amines has been developed. N-Substituted phthalimides were produced in good to excellent yields. Furthermore, thalidomide was produced in excellent yield under these conditions.
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Bis-chlorination of a hexapeptide-PCP conjugate by the halogenase involved in vancomycin biosynthesis

15 July, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,5574-5577
DOI: 10.1039/C4OB00474D, CommunicationOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Patrick C. Schmartz, Katja Zerbe, Khaled Abou-Hadeed, John A. Robinson
The vancomycin biosynthetic halogenase can bis-chlorinate both [small beta]-hydroxytyrosine residues-2 and -6 in a model substrate comprising a PCP-linked hexapeptide.
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Conversion of S-phenylsulfonylcysteine residues to mixed disulfides at pH 4.0: utility in protein thiol blocking and in protein-S-nitrosothiol detection

13 July, 2014 - 07:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00995A, PaperB. D. Reeves, N. Joshi, G. C. Campanello, J. K. Hilmer, L. Chetia, J. A. Vance, J. N. Reinschmidt, C. G. Miller, D. P. Giedroc, E. A. Dratz, D. J. Singel, P. A. Grieco
A protocol denoted as the thiosulfonate switch featuring sequential protein thiol blocking and conversion of protein-S-nitrosothiols to mixed disulfides bearing a fluorescent probe at pH 4.0 is reported.
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A tryptophan responsive fluorescent and wettable dual-signal switch

13 July, 2014 - 07:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00792A, PaperXiaoyan Zhang, Jing Li, Ningmei Feng, Li Luo, Zhen Dai, Li Yang, Demei Tian, Haibing Li
A new fluorescent dianthracene calix[4]arene (C4DA) was designed and synthesized via coupling the fluorescent anthracene units and calix[4]arene units.
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