- Silver-Catalyzed Decarboxylative Azidation of Aliphatic Carboxylic Acids
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The catalytic decarboxylative nitrogenation of aliphatic carboxylic acids for the synthesis of alkyl azides is reported. A series of tertiary, secondary, and primary organoazides were prepared from easily available aliphatic carboxylic acids by using K2S2O8 as the oxidant and PhSO2N3 as the nitrogen source. The EPR experiment sufficiently proved that an alkyl radical process was generated in the process, and DFT calculations further supported the SET process followed by a stepwise SH2 reaction to afford azide product.
- Zhu, Yuchao,Li, Xinyao,Wang, Xiaoyang,Huang, Xiaoqiang,Shen, Tao,Zhang, Yiqun,Sun, Xiang,Zou, Miancheng,Song, Song,Jiao, Ning
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- A novel and highly selective conversion of alcohols, thiols, and silyl ethers to azides using the triphenylphosphine/2,3-dichloro-5,6- dicyanobenzoquinone(DDQ)/n-Bu4NN3 system
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Alcohols, thiols, and silyl ethers are converted into alkyl azides in good to excellent yields by treatment with PPh3/DDQ/n-Bu 4NN3 in CH2Cl2 at room temperature. The method is highly selective for 1°
- Iranpoor, Nasser,Firouzabadi, Habib,Akhlaghinia, Batool,Nowrouzi, Najmeh
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- THE IR AND RAMAN SPECTRA AND CONFORMATIONS OF CYCLOHEXYL AZIDE
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Cyclohexyl azide was synthesized and the vibrational spectra recorded in several phases including: liquid at various temperatures, amorphous and crystalline at 90 K and high pressure crystal at ca. 60 kbar.Additional IR spectra were recorded in argon and
- Suelzle, D.,Gatial, A.,Karlsson, A.,Klaeboge, P.,Nielsen, C. J.
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- Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions
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Nickel boride catalyst prepared in situ from NiCl2 and sodium borohydride allowed, in the presence of an aqueous solution of TEMPO-oxidized nanocellulose (0.01 wt%), the reduction of a wide range of nitroarenes and aliphatic nitro compounds. Here we describe how the modified nanocellulose has a stabilizing effect on the catalyst that enables low loading of the nickel salt pre-catalyst. Ni-B prepared in situ from a methanolic solution was also used to develop a greener and facile reduction of organic azides, offering a substantially lowered catalyst loading with respect to reported methods in the literature. Both aromatic and aliphatic azides were reduced, and the protocol is compatible with a one-pot Boc-protection of the obtained amine yielding the corresponding carbamates. Finally, bacterial crystalline nanocellulose was chosen as a support for the Ni-B catalyst to allow an easy recovery step of the catalyst and its recyclability for new reduction cycles.
- Proietti, Giampiero,Prathap, Kaniraj Jeya,Ye, Xinchen,Olsson, Richard T.,Dinér, Peter
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supporting information
p. 133 - 146
(2021/11/04)
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- A general procedure for carbon isotope labeling of linear urea derivatives with carbon dioxide
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Carbon isotope labeling is a traceless technology, which allows tracking the fate of organic compounds either in the environment or in living organisms. This article reports on a general approach to label urea derivatives with all carbon isotopes, including14C and11C, based on a Staudinger aza-Wittig sequence. It provides access to all aliphatic/aromatic urea combinations.
- Babin, Victor,Sallustrau, Antoine,Loreau, Olivier,Caillé, Fabien,Goudet, Amélie,Cahuzac, Hélo?se,Del Vecchio, Antonio,Taran, Frédéric,Audisio, Davide
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supporting information
p. 6680 - 6683
(2021/07/12)
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- Conformational energy (A-value) of the 4-phenyl-1,2,3-triazolyl group
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Conformational energy (A-value) of the 4-phenyl-1,2,3- triazolyl group was estimated as 2.0 kcal mol–1 (8.5 kJ mol–1) using 1H NMR-based conformational study for a set of (4-phenyl-1,2,3-triazol-1-yl)cyclohexanes. This provides a reasonable estimation als
- Ruyonga, Mulinde R.,Samoshin, Vyacheslav V.
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p. 609 - 611
(2021/11/09)
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- Cyclic Diaryl λ3-Bromanes: A Rapid Access to Molecular Complexity via Cycloaddition Reactions
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Biaryls have widespread applications in organic synthesis. However, sequentially polysubstituted biaryls are underdeveloped due to their challenging preparation. Herein, we report the synthesis of dissymetric 2,3,2′,3′,4-substituted biaryls via pericyclic reactions of cyclic diaryl λ3-bromanes. The functional groups tolerance and atom economy allow access to molecular complexity in a single reaction step. Continuous flow protocol has been designed for the scale-up of the reaction, while postfunctionalizations have been developed taking advantage of the residual Br-atom.
- Lanzi, Matteo,Ali Abdine, Racha Abed,De Abreu, Maxime,Wencel-Delord, Joanna
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supporting information
p. 9047 - 9052
(2021/12/06)
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- Visible-Light-Mediated Strategies to Assemble Alkyl 2-Carboxylate-2,3,3-Trisubstituted β-Lactams and 5-Alkoxy-2,2,4-Trisubstituted Furan-3(2H)-ones Using Aryldiazoacetates and Aryldiazoketones
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Two new visible-light-mediated strategies are described starting from aryldiazoacetates. The first approach describes their reaction with azides to afford the corresponding imines, and then reaction with aryldiazoketones produces alkyl 2-carboxylate-2,3,3
- Deflon, Victor M.,Dos Santos, Caio Y.,Gallo, Rafael D. C.,Jurberg, Igor D.,Munaretto, Laiéli S.,Okada, Celso Y.
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supporting information
p. 9292 - 9296
(2021/12/06)
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- Furfuryl Cation Induced Three-Component Reaction to Synthesize Triazole-Substituted Thioesters
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A furfuryl cation induced three-component thioesterification reaction between thiols, 5-bromo-2-furylcarbinols and azides is reported. This metal-free method relies on the acetyl chloride/HFIP-mediated cascade formal [3+2] cycloaddition/ring-opening/thioesterification, which allows the efficient construction of a series of complex triazole-thioesters linked with an (Z)-olefin. Selenols are also suitable for this strategy. Further derivatization of thioesters highlighted the potential utility of our method.
- Zhong, Ying,Xu, Xiaoming,Xing, Qingzhao,Yang, Song,Gou, Jing,Gao, Ziwei,Yu, Binxun
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supporting information
p. 3251 - 3256
(2020/05/25)
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- Synthesis, characterization and catalytic properties of a new binuclear copper(II) complex in the azide–alkyne cycloaddition
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A new binuclear copper(II)–oxalate complex containing 2,9-dimethyl-1,10-phenanthroline (dmp), was synthesized via a simple and one-pot reaction. [Cu2(dmp)2(ox)Cl2]·H2O (1) was characterized by single-crystal X-ray crystallography and IR methods. The complex 1 was been used to efficiently catalyze the three-component 1,3-Dipolar cycloaddition CuAAC reaction to produce 1,4-disubstituted 1,2,3‐triazoles in good to excellent yields from aromatic or aliphatic halide, sodium azide, and acetylene in water as a green solvent with low catalyst amount.
- Akbar Khandar, Ali,Amini, Mojtaba,Ellern, Arkady,Keith Woo, L.,Sheykhi, Ayda
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- Synthesis of (1,2,3‐triazol‐4‐yl)methyl phosphinates and (1,2,3‐Triazol‐4‐yl)methyl phosphates by copper‐catalyzed azide‐alkyne cycloaddition
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An efficient and practical method was developed for the synthesis of new (1,2,3‐triazol‐4‐yl)methyl phosphinates and (1,2,3‐triazol‐4‐yl)methyl phosphates by the copper(I)‐catalyzed azide‐alkyne cycloaddition (CuAAC) of organic azides and prop‐2‐ynyl phos
- Tripolszky, Anna,Németh, Krisztina,Szabó, Pál Tamás,Bálint, Erika
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- Reactions of α-haloacroleins with azides: Highly regioselective synthesis of formyl triazoles
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A general metal-free route to 1,4-disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles was developed. α-Haloacroleins reacted with organic azides in a DMSO/H2O mixture solvent at room temperature to produce 1,4-disubstituted triazoles (up to 99%) with exclusive regioselectivities. This protocol is convenient and scalable with a broad substrate scope including aliphatic and aromatic azides. The resulting triazoles exhibited an aldehyde group at the C4 position and demonstrated synthetic utilizations. One 1,2,3-triazole compound containing diastereotopic protons was also identified.
- Zhang, Dongsheng,Fan, Yingzhu,Yan, Zhongliang,Nie, Yi,Xiong, Xingquan,Gao, Lizhu
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supporting information
p. 4211 - 4216
(2019/08/07)
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- Synergistic combination of visible-light photo-catalytic electron and energy transfer facilitating multicomponent synthesis of β-functionalized α,α-diarylethylamines
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A synthetic strategy with the visible-light photo-catalytic synergistic combination of electron and energy transfer processes has been developed. The mild reaction conditions allow the radical-radical cross-coupling phenomenon for the multicomponent synthesis of β-arylsulfonyl(diarylphosphinoyl)-α,α-diarylethyl-amines from readily available arylsulfinic acids (diarylphosphine oxides), 1,1-diarylethylenes and arylazides.
- Wu, Yanan,Zhang, Yipin,Jiang, Mingjie,Dong, Xunqing,Jalani, Hitesh B.,Li, Guigen,Lu, Hongjian
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supporting information
p. 6405 - 6408
(2019/06/07)
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- A General Strategy for Aliphatic C-H Functionalization Enabled by Organic Photoredox Catalysis
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Synthetic transformations that functionalize unactivated aliphatic C-H bonds in an intermolecular fashion offer unique strategies for the synthesis and late-stage derivatization of complex molecules. Herein we report a general approach to the intermolecular functionalization of aliphatic C-H bonds using an acridinium photoredox catalyst and phosphate salt under blue LED irradiation. This strategy encompasses a range of valuable C-H transformations, including the direct conversions of a C-H bond to C-N, C-F, C-Br, C-Cl, C-S, and C-C bonds, in all cases using the alkane substrate as the limiting reagent. Detailed mechanistic studies are consistent with the intermediacy of a putative oxygen-centered radical as the hydrogen atom-abstracting species in these processes.
- Margrey, Kaila A.,Czaplyski, William L.,Nicewicz, David A.,Alexanian, Erik J.
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supporting information
p. 4213 - 4217
(2018/04/05)
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- [3 + 3] Cycloaddition of azides with in situ formed azaoxyallyl cations to synthesize 1,2,3,4-Tetrazines
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A formal [3 + 3] cycloaddition reaction between azides and in situ formed azaoxyallyl cations has been realized. This reaction provided an efficient and practical pathway to synthesize 1,2,3,4-tetrazines in good yields under mild conditions. Biologically active molecules could also be well compatible, highlighting the potential value of this reaction.
- Xu, Xiaoying,Zhang, Kaifan,Li, Panpan,Yao, Hequan,Lin, Aijun
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supporting information
p. 1781 - 1784
(2018/04/14)
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- Synthesis, Characterization, and Antimicrobial Activity of a Series of 2-(5-Phenyl-1,3,4-oxadiazol-2-yl)-N-[(1-aryl-1H-1,2,3-triazol-4-yl)methyl]anilines Using Click Chemistry
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series of new triazolyl derived 1,3,4-oxadiazoles 7a–7l is synthesized with high yields by coppercatalyzed alkyne–azide cycloaddition reaction between a variety of substituted aryl/alkyl azides and 2-(5-phenyl-1,3,4-oxadiazol-2-yl)aniline. Structures of intermediates and the final compounds are confirmed by FTIR, 1H and 13C NMR, and Mass spectra. The synthesized compounds demonstrate moderate antibacterial activity and potent antifungal activity against the tested strains.
- Venkatagiri,Krishna,Thirupathi,Bhavani,Reddy
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p. 1488 - 1494
(2018/09/10)
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- Discovery of Novel 11-Triazole Substituted Benzofuro[3,2-b]quinolone Derivatives as c-myc G-Quadruplex Specific Stabilizers via Click Chemistry
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The specificity of nucleic acids' binders is crucial for developing this kind of drug, especially for novel G-quadruplexes' binders. Quindoline derivatives have been developed as G-quadruplex stabilizers with good interactive activities. In order to improve the selectivity and binding affinity of quindoline derivatives as c-myc G-quadruplex binding ligands, novel triazole containing benzofuroquinoline derivatives (T-BFQs) were designed and synthesized by using the 1,3-dipolar cycloaddition of a series of alkyne and azide building blocks. The selectivity toward c-myc G-quadruplex DNA of these novel T-BFQs was significantly improved, together with an obvious increase on binding affinity. Further cellular and in vivo experiments indicated that the T-BFQs showed inhibitory activity on tumor cells' proliferation, presumably through the down-regulation of transcription of c-myc gene. Our findings broadened the modification strategies of specific G-quadruplex stabilizers.
- Zeng, De-Ying,Kuang, Guo-Tao,Wang, Shi-Ke,Peng, Wang,Lin, Shu-Ling,Zhang, Qi,Su, Xiao-Xuan,Hu, Ming-Hao,Wang, Honggen,Tan, Jia-Heng,Huang, Zhi-Shu,Gu, Lian-Quan,Ou, Tian-Miao
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supporting information
p. 5407 - 5423
(2017/07/22)
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- Selective C(sp2)-H Halogenation of "click" 4-Aryl-1,2,3-triazoles
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Selective bromination reactions of "click compounds" are described. Electron-neutral and electron-deficient arenes selectively undergo unprecedented Pd-catalyzed C-H ortho-halogenations assisted by simple triazoles as modular directing groups, whereas electron-rich arenes are regioselectively halogenated following an electrophilic aromatic substitution reaction pathway. These C-H halogenation procedures exhibit a wide group tolerance, complement existing bromination procedures, and represent versatile synthetic tools of utmost importance for the late-stage diversification of "click compounds". The characterization of a triazole-containing palladacycle and density functional theory studies supported the mechanism proposal.
- Goitia, Asier,Gómez-Bengoa, Enrique,Correa, Arkaitz
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supporting information
p. 962 - 965
(2017/02/26)
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- Synthesis and antibacterial activity of novel 4″-O-(1-aralkyl-1,2,3-triazol-4-methyl-carbamoyl) azithromycin analogs
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Three novel structural series of 4″-O-(1-aralkyl-1,2,3-triazol-4-methyl-carbamoyl) azithromycin analogs were designed, synthesized and evaluated for their in vitro antibacterial activity. All the target compounds exhibited excellent activity against erythromycin-susceptible Streptococcus pyogenes, and significantly improved activity against three phenotypes of erythromycin-resistant Streptococcus pneumoniae compared with clarithromycin and azithromycin. Among the three series of azithromycin analogs, the novel series of 11,4″-disubstituted azithromycin analogs 9a–k exhibited the most effective and balanced activity against susceptible and resistant bacteria. Among them, compound 9j showed the most potent activity against Staphylococcus aureus ATCC25923 (0.008?μg/mL) and Streptococcus pyogenes R2 (1?μg/mL). Besides, all the 11,4″-disubstituted azithromycin analogs 9a–k except 9f shared the identical activity with the MIC value 0.002?μg/mL against Streptococcus pyogenes S2. Furthermore, compounds 9g, 9h, 9j and 9k displayed significantly improved activity compared with the references against all the three phenotypes of resistant S. pneumoniae. Particularly, compound 9k was the most effective (0.06, 0.03 and 0.125?μg/mL) against all the erythromycin-resistant S. pneumoniae expressing the erm gene, the mef gene and the erm and mef genes, exhibiting 2133, 133 and 2048-fold more potent activity than azithromycin, respectively.
- Wang, Yinhu,Cong, Chao,Chern Chai, Wern,Dong, Ruiqian,Jia, Li,Song, Di,Zhou, Ziteng,Ma, Shutao
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supporting information
p. 3872 - 3877
(2017/07/27)
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- Intermolecular Schmidt reaction of alkyl azides with acyl silanes
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The first intermolecular Schmidt reaction of alkyl azides with acyl silanes has been designed and realized, producing a range of amides with absolute site selectivity in good to excellent yields. The mechanism of the conversion has been proposed, and the reaction exhibits scope of substrates.
- Yu, Chun-Jiao,Li, Rui,Gu, Peiming
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supporting information
p. 3568 - 3570
(2016/07/18)
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- Synthesis, Antibacterial, and Anticancer Evaluation of Novel Spiramycin-Like Conjugates Containing C(5) Triazole Arm
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Huisgen cycloaddition allowed obtaining of novel triazole-bridged antibiotics (6-16) with the reconstructed C(5) arm of spiramycin. 1H-1H NOESY couplings indicated the structure of novel derivatives in solution and demonstrated that
- Klich, Katarzyna,Pyta, Krystian,Kubicka, Marcelina M.,Ruszkowski, Piotr,Celewicz, Lech,Gajecka, Marzena,Przybylski, Piotr
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p. 7963 - 7973
(2016/09/23)
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- Synthesis of novel 5-[(1,2,3-triazol-4-yl)methyl]-1-methyl-3H-pyridazino[4,5-b]indol-4-one derivatives by click reaction and exploration of their anticancer activity
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A series of pyridazino[4,5-b]indole derivatives containing alkyl-, benzyl- and phenacyl-substituted 1,2,3-triazolylmethyl units was synthesized using click chemistry approach. All 30 compounds of the series were screened in vitro against four cancer cell lines, viz. breast cancer cells MDA-MB-231 and MCF 7, human primary glioblastoma U-87 and human neuroblastoma IMR-32 cell lines. Most of the compounds exhibited potent cancer cell growth inhibition activity at very low micromolar concentrations. The IC50 value of compounds 7v and 7x against human neuroblastoma IMR-32 cell line is 0.07 and 0.04 μM, respectively. Among the tested compounds, ten compounds showed IC50 value less than 1 μM against MDA-MB-231 cells, whereas against IMR-32 cells, nine compounds and, against U-87 cells, six compounds showed similar inhibition activity. Further, these molecules exhibited prominent binding affinity and docking scores in the molecular simulation study with the target enzyme PI3 kinase. Graphical Abstract: This paper illustrates the synthesis of new fused indole-pyridazinone derivatives containing substituted 1,2,3-triazoles via click chemistry approach. Most of the compounds exhibited potent cancer cell growth inhibition activity at very low micromolar concentrations. [Figure not available: see fulltext.]
- Panathur, Naveen,Gokhale, Nikhila,Dalimba, Udayakumar,Koushik, Pulla Venkat,Yogeeswari, Perumal,Sriram, Dharmarajan
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p. 135 - 148
(2016/01/25)
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- Carboxylate-Assisted Iridium-Catalyzed C-H Amination of Arenes with Biologically Relevant Alkyl Azides
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An iridium-catalyzed C-H amination of arenes with a wide substrate scope is reported. Benzamides with electron-donating and -withdrawing groups and linear, branched, and cyclic alkyl azides are all applicable. Cesium carboxylate is crucial for both reactivity and regioselectivity of the reactions. Many biologically relevant molecules, such as amino acid, peptide, steroid, sugar, and thymidine derivatives can be introduced to arenes with high yields and 100 % chiral retention. Ir responsible! A direct C-H amination between benzamide derivatives and various alkyl azides was achieved using iridium catalysis (see scheme; NTf=trifluoromethanesulfonyl amide). Cesium carboxylate was found to be the promoter and regiocontroller of this reaction. By this method, many biological active molecules can be introduced to benzamide components with high yields and 100 % chiral retention.
- Zhang, Tao,Hu, Xuejiao,Wang, Zhen,Yang, Tiantian,Sun, Hao,Li, Guigen,Lu, Hongjian
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supporting information
p. 2920 - 2924
(2016/03/23)
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- Discovery of 7-Methyl-10-Hydroxyhomocamptothecins with 1,2,3-Triazole Moiety as Potent Topoisomerase I Inhibitors
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Homocamptothecin is emerging as an important topoisomerase I inhibitor originating in natural product camptothecin. We report the modifications and SAR of homocamptothecin on position C10 to develop potent topoisomerase I inhibitors for anticancer drug di
- Xu, Xiguo,Wu, Yuelin,Liu, Wenfeng,Sheng, Chuanquan,Yao, Jianzhong,Dong, Guoqiang,Fang, Kun,Li, Jin,Yu, Zhiliang,Min, Xiao,Zhang, Huojun,Miao, Zhenyuan,Zhang, Wannian
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p. 398 - 403
(2016/10/19)
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- Manganese-catalyzed late-stage aliphatic C-H azidation
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We report a manganese-catalyzed aliphatic C-H azidation reaction that can efficiently convert secondary, tertiary, and benzylic C-H bonds to the corresponding azides. The method utilizes aqueous sodium azide solution as the azide source and can be performed under air. Besides its operational simplicity, the potential of this method for late-stage functionalization has been demonstrated by successful azidation of various bioactive molecules with yields up to 74%, including the important drugs pregabalin, memantine, and the antimalarial artemisinin. Azidation of celestolide with a chiral manganese salen catalyst afforded the azide product in 70% ee, representing a Mn-catalyzed enantioselective aliphatic C-H azidation reaction. Considering the versatile roles of organic azides in modern chemistry and the ubiquity of aliphatic C-H bonds in organic molecules, we envision that this Mn-azidation method will find wide application in organic synthesis, drug discovery, and chemical biology.
- Huang, Xiongyi,Bergsten, Tova M.,Groves, John T.
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supporting information
p. 5300 - 5303
(2015/05/13)
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- Transition-Metal-Free Oxidative Aliphatic C-H Azidation
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The first example of a practical and selective azidation of unactivated aliphatic C-H bonds with easily handled sulfonyl azides as azide source without the use of transition metals has been explored. This method is operationally simple, scalable, and applicable to late-stage azidation of natural products and derivatives, which make it a valuable method for the synthesis of organic azides.
- Zhang, Xiaofei,Yang, Haodong,Tang, Pingping
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supporting information
p. 5828 - 5831
(2015/12/11)
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- Synthesis, characterization, and antimicrobial activity of new bis-1,2,3-triazol-H-yl-substituted 2-arylbenzimidazoles
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New bis-1,2,3-triazol-H-yl-substituted 2-aryl benzimidazoles VIa-VIp were synthesized from O- and N-bis-propargyl substituted 2-arylbenzimidazoles using "click chemistry." The newly synthesized compounds were characterized by IR, NMR, and mass spectra. Th
- Subhashini,Boddu, Lingaiah,Amanaganti, Jampaiah,Shivaraj
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p. 1442 - 1449
(2014/10/15)
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- A reagent for safe and efficient diazo-transfer to primary amines: 2-azido-1,3-dimethylimidazolinium hexafluorophosphate
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Organic azides were prepared from primary amines in high yields by a metal free diazo-transfer reaction using 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP), which is safe and stable crystalline. The choice of base was important in the diazo-transfer reaction. In general, 4-(N,N-dimethyl)aminopyridine (DMAP) was efficient, but a stronger base such as alkylamine or DBU was more appropriate for the reaction of nucleophilic primary amines. X-ray single crystal structural analysis and geometry optimization using density functional theory (B3LYP/6-31G**) were conducted to study the ADMP structure, and the diazo-transfer reaction mechanism was explained with the help of the results of these analyses. the Partner Organisations 2014.
- Kitamura, Mitsuru,Kato, So,Yano, Masakazu,Tashiro, Norifumi,Shiratake, Yuichiro,Sando, Mitsuyoshi,Okauchi, Tatsuo
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p. 4397 - 4406
(2014/06/23)
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- A dicationic, podand-like, ionic liquid water system accelerated copper-catalyzed azide-alkyne click reaction
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In this work, an effective, task specific, dicationic, podand-like ionic liquid was synthesized and applied to improve the capability features of click reaction. Moreover, to broaden the scope and decreasing the serious limitations of preparation methods of organic azides, a simple green procedure for the preparation of alkyl azides, the fundamental starting materials in click reactions, from alcohols under solvent-free conditions and microwave irradiation has been reported, for the first time.
- Javaherian, Mohammad,Kazemi, Foad,Ghaemi, Masoumeh
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p. 1643 - 1647
(2015/01/09)
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- Exploiting the Nucleophilicity of N-H Imines: Synthesis of Enamides from Alkyl Azides and Acid Anhydrides
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The nucleophilicity of N-unsubstituted imines, which were generated from alkyl azides by a ruthenium-catalyzed reaction, was investigated in the reaction with acid anhydrides. The initial products were N-acylimines, which isomerized to the corresponding e
- Han, Junghoon,Jeon, Mina,Pak, Han Kyu,Rhee, Young Ho,Park, Jaiwook
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supporting information
p. 2769 - 2774
(2016/02/18)
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- Ln[N(SiMe3)2]3-catalyzed cycloaddition of terminal alkynes to azides leading to 1,5-disubstituted 1,2,3-triazoles: New mechanistic features
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The first example of rare earth metal-catalyzed cycloaddition of terminal alkynes to azides resulting in the formation of 1,5-disubstituted 1,2,3-triazoles is described. Preliminary studies revealed that the present cycloaddition shows unprecedented mecha
- Hong, Longcheng,Lin, Weijia,Zhang, Fangjun,Liu, Ruiting,Zhou, Xigeng
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supporting information
p. 5589 - 5591
(2013/07/25)
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- Alkyne phosphonites for sequential azide-azide couplings
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When Staudinger meets Huisgen! A combination of the copper-catalyzed variant of the Huisgen azide-alkyne cycloaddition (CuAAC) and the Staudinger reaction, the two most successful chemoselective reactions for the transformation of azides, leads to a chemi
- Vallée, M. Robert J.,Artner, Lukas M.,Dernedde, Jens,Hackenberger, Christian P. R.
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supporting information
p. 9504 - 9508
(2013/09/23)
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- Alkyne-azide cycloadditions with copper powder in a high-pressure continuous-flow reactor: High-temperature conditions versus the role of additives
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A safe and efficient flow-chemistry-based procedure is presented for 1,3-dipolar cycloaddition reactions between organic azides and acetylenes. This simple and inexpensive technique eliminates the need for costly special apparatus and utilizes Cu powder a
- Oetvoes, Sandor B.,Mandity, Istvan M.,Kiss, Lorand,Fueloep, Ferenc
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p. 800 - 808
(2013/05/09)
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- Bifunctional iminophosphorane organocatalysts for enantioselective synthesis: Application to the ketimine nitro-Mannich reaction
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The design, synthesis, and development of a new class of modular, strongly basic, and tunable bifunctional Bronsted base/H-bond-donor organocatalysts are reported. These catalysts incorporate a triaryliminophosphorane as the Bronsted basic moiety and are readily synthesized via a last step Staudinger reaction of a chiral organoazide and a triarylphosphine. Their application to the first general enantioselective organocatalytic nitro-Mannich reaction of nitromethane to unactivated ketone-derived imines allows the enantioselective construction of β-nitroamines possessing a fully substituted carbon atom. The reaction is amenable to multigram scale-up, and the products are useful for the synthesis of enantiopure 1,2-diamine and α-amino acid derivatives.
- Nunez, Marta G.,Farley, Alistair J. M.,Dixon, Darren J.
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supporting information
p. 16348 - 16351
(2013/12/04)
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- Unexpected conversion of alkyl azides to alkyl iodides and of aryl azides to N-tert-butyl anilines
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In the presence of tert-butyl iodide, alkyl azides are converted into the corresponding iodides at room temperature, whereas, N-t-Bu anilines are obtained from aryl azides under the same experimental conditions. A mechanism is proposed to explain this unusual reactivity.
- Maury, Julien,Feray, Laurence,Bertrand, Michele P.,Kapat, Ajoy,Renaud, Philippe
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p. 9606 - 9611,6
(2020/08/20)
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- C-H and C-C bond formation promoted by facile κ3/ κ2 interconversions in a hemilabile "click"-triazole scorpionate platinum system
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A series of platinum complexes bearing 3-fold symmetrical "Click"-triazole-based scorpionate ligands (TtR) has been prepared. Metalation of these weakly donating ligands results in neutral Pt(II) complexes that display a κ2 coordinat
- Frauhiger, Bryan E.,White, Peter S.,Templeton, Joseph L.
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experimental part
p. 225 - 237
(2012/04/23)
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- Magnetic copper-iron nanoparticles as simple heterogeneous catalysts for the azide-alkyne click reaction in water
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The development of a novel bimetallic copper-iron nanoparticle synthesis provides a recoverable heterogeneous catalyst for the azide-alkyne "click" reaction in water. The nanoparticles catalyze the production of a diverse range of triazoles, while separat
- Hudson, Reuben,Li, Chao-Jun,Moores, Audrey
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experimental part
p. 622 - 624
(2012/05/04)
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- FeCl2-promoted cleavage of the unactivated C-C bond of alkylarenes and polystyrene: Direct synthesis of arylamines
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Ironing it out: An efficient and convenient nitrogenation strategy involving C-C bond cleavage for the straightforward synthesis of versatile arylamines is presented. Various alkyl azides and alkylarenes, including the common industrial by-product cumene, react using this protocol. Moreover, this method provides a potential strategy for the degradation of polystyrene. Copyright
- Qin, Chong,Shen, Tao,Tang, Conghui,Jiao, Ning
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supporting information; experimental part
p. 6971 - 6975
(2012/09/25)
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- A practical one-pot synthesis of azides directly from alcohols
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Alkyl/benzyl azides can be readily synthesized in excellent yields from their corresponding alcohols by stirring a solution of sodium azide in DMSO with a thoroughly ground equimolecular mixture of triphenylphosphine, iodine and imidazole. Indian Academy
- Rokhum, Lalthazuala,Bez, Ghanashyam
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experimental part
p. 687 - 691
(2012/08/07)
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- Ionic liquid brush as a highly efficient and reusable catalyst for on-water nucleophilic substitutions
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A very efficient and reusable catalyst has been developed for the on-water nucleophilic substitution of alkyl halides and tosylates with azide or thiocyanate in excellent to quantitative yields. The reaction proceeds smoothly and cleanly without any organic cosolvent or other adductive, and the brush can be reused at least 10 times without noticeable loss of the catalytic activity. The high efficiency, simplicity of product and catalyst isolation, outstanding recyclability, and organic-solvent-free conditions show promise for the use of this catalyst in the laboratory and in industry. A highly efficient and reusable ionic liquid brush catalyst has been developed for the on-water nucleophilic substitution of alkyl halides and tosylates with azide or thiocyanate in excellent to quantitative yields without any organic cosolvent or other adductive. The catalyst can be reused at least 10 times without noticeable loss of the catalytic activity. Copyright
- Li, Jing,Cao, Jing-Jing,Wei, Jun-Fa,Shi, Xian-Ying,Zhang, Li-Hui,Feng, Jin-Juan,Chen, Zhan-Guo
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supporting information; experimental part
p. 229 - 233
(2011/03/20)
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- First multipurpose task specific ionic liquid: Designing and synthesis of novel dimethyl formamide-like ionic liquid and its applications as a green solvent alternative to dimethyl formamide dependent reactions
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A novel imidazole based task specific ionic liquid with dimethyl formamide (DMF) functionality has been designed and synthesized. The proposed dimethyl formamide like task specific can be used as a green alternative solvent-cum-organocatalyst for wide range of organic reactions which essentially depend on DMF. Dimethyl formamide as a solvent, due to its inherited structural features is found to affect the outcome of many reactions. Some of DMF-dependent reactions are investigated in its ionic liquid version with encouraging results. DMFlike ionic liquid acts both as a green reaction media and recyclable organocatalyst. Main advantages include easy reaction procedure, short reaction duration, easy work up and moreover the wide scope applications.
- Hullio, Ahmed Ali,Mastoi,Khan, Khalid
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experimental part
p. 5411 - 5418
(2012/06/29)
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- Triazole-pyridine ligands: A novel approach to chromophoric iridium arrays
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We describe a novel modular approach to a series of luminescent iridium complexes bearing triazole-pyridine-derived ligands that were conveniently prepared by using "click" chemistry. One, two or three triazole-pyridine units were effectively built into the heteroaromatic macromolecule using versatile acetylene- and azide-functionalised precursors. Using this approach, a series of iridium-derived molecules, that differ in the number of iridium centres, the structural characteristics of the cyclometalating ligand and the backbone, were synthesised. The preliminary photophysical properties of the prepared complexes indicate that there is only limited interaction (through space or through the backbone) between the iridium centres within one molecule and that each iridium centre retains its individual properties. The results show that our approach can be generally applied towards covalently linked multichromophoric systems with potential application, for instance, in the design and preparation of tunable light emitters. As a demonstration of this concept, a single molecule white-light emitter, constructed from two iridium centres (yellow emission) and a fluorene unit (blue emission), is presented. The Royal Society of Chemistry.
- Juriek, Michal,Felici, Marco,Contreras-Carballada, Pablo,Lauko, Jan,Bou, Sandra Rodriguez,Kouwer, Paul H. J.,Brouwer, Albert M.,Rowan, Alan E.
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supporting information; experimental part
p. 2104 - 2111
(2011/10/02)
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- A radical procedure for the anti-markovnikov hydroazidation of alkenes
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A one-pot procedure for the efficient hydroazidation of alkenes involving hydroboration with catecholborane followed by reaction with benzenesulfonyl azide in the presence of a radical initiator is described. The regioselectivity is controlled by the hydroboration step and corresponds in most cases to an anti-Markovnikov regioselectivity. This procedure is applicable to a wide range of alkenes and gives excellent results with 1,2-disubstituted and trisubstituted alkenes.
- Kapat, Ajoy,Koenig, Andreas,Montermini, Florian,Renaud, Philippe
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supporting information; experimental part
p. 13890 - 13893
(2011/10/31)
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- Direct synthesis of organic azides from primary amines with 2-azido-1,3-dimethylimidazolinium hexafluorophosphate
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Organic azides were prepared from primary amines in high yields by metal-free diazo transfer with 2-azido-1,3-dimethylimidazolinium hexafluorophosphate, which is a stable, crystalline solid that is easy to handle. Organic azides were prepared from primary
- Kitamura, Mitsuru,Yano, Masakazu,Tashiro, Norifumi,Miyagawa, Satoshi,Sando, Mitsuyoshi,Okauchi, Tatsuo
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experimental part
p. 458 - 462
(2011/03/18)
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- Effects of a flexible alkyl chain on a ligand for CuAAC reaction
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Imidazole derivatives substituted by a normal alkyl group are shown to be efficient as a ligand for the copper(Δ)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction. An alkyl chain on the imidazole ligands shows an efficient steric effect and benefits the reaction. Such functionalities of an alkyl chain allow a rapid CuAAC reaction of even a bulky alkyne, which has been difficult to perform under conventional conditions.
- Asano, Keisuke,Matsubara, Seijiro
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supporting information; experimental part
p. 4988 - 4991
(2010/12/25)
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- Unsupported copper nanoparticles in the 1,3-dipolar cycloaddition of terminal alkynes and azides
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Readily prepared copper nanoparticles were found to catalyse the 1,3-dipolar cycloaddition of azides and alkynes up to rates comparable to those of microwave chemistry. Both the preparation of the nanoparticles and the click reaction are carried out under mild conditions, in short reaction times and in the absence of any stabilising additive or ligand. A variety of 1,2,3-triazoles were prepared in excellent yields. A reaction mechanism was postulated on the basis of different reactivity studies and deuteration experiments. Copper(I) acetylides were demonstrated to be the real intermediate species.
- Alonso, Francisco,Moglie, Yanina,Radivoy, Gabriel,Yus, Miguel
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supporting information; experimental part
p. 1875 - 1884
(2010/07/18)
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- Heteroarylalkyl-8-azabicyclo[3.2.1]octane compounds as mu opioid receptor antagonists
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The invention provides heteroarylene substituted 8-azabicyclo[3.2.1]octane compounds of formula (I): wherein R1, R2, A, and m are defined in the specification, or a pharmaceutically-acceptable salt thereof, that are antagonists at th
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Page/Page column 15
(2009/04/24)
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- Microwave irradiation as an effective means of synthesizing uninfstituted N-linked 1,2,3-triazoles from vinyl acetate and azides
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N-Linked 1,2,3-triazoles have been prepared by a reaction of azides with vinyl acetate under microwave irradiation. Additionally, a microwave-assisted, two-step, one-pot procedure from halides involving azideinfstitution in diethyl ether, followed by -reaction with vinyl acetate, has effectively been employed. Georg Thieme Verlag Stuttgart - New York.
- Hansen, Signe Grann,Jensen, Henrik Helligs?
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experimental part
p. 3275 - 3278
(2010/03/03)
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- A simple one-pot procedure for the direct conversion of alcohols into azides using TsIm
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A facile and efficient method for one-pot conversion of alcohols into azides using N-(p-toluenesulfonyl)imidazole (TsIm) is described. In this method, alcohols are refluxed with a mixture of NaN3, TsIm and triethylamine in the presence of catalytic amounts of tetra-n-butylammonium iodide (TBAI) in DMF affording the corresponding alkyl azides in good yields. This methodology is highly efficient for various structurally diverse alcohols with selectivity for ROH: 1° > 2° > 3°.
- Soltani Rad, Mohammad Navid,Behrouz, Somayeh,Khalafi-Nezhad, Ali
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p. 3445 - 3449
(2008/02/10)
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- Oxidation of azides by the HOF·CH3CN: A novel synthesis of nitro compounds
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The HOF·CH3CN complex, readily prepared by passing F 2 through aqueous acetonitrile, is an exceptionally efficient oxygen transfer agent. It is unique in its capacity to oxidize various azides into the corresponding nitro derivatives. This method requires short reactions times and room temperature or below, and the desired nitro compounds were usually isolated in very good yields. The respective nitroso derivatives are believed to be the intermediates in this reaction. Functional groups such as aromatic rings, ketones, nitriles, halides, alcohols, and esters are tolerated. Sulfides react with HOF·CH3CN usually at the same rate as azides. Amines and olefins, however, react faster, so they have to be protected first. Nitro derivatives with various oxygen isotopes can be made using the labeled H 18OF·CH3CN. In the case of chiral azides the stereochemistry around the nitrogen-bonded carbons is retained.
- Carmeli, Mira,Rozen, Shlomo
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p. 4585 - 4589
(2007/10/03)
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- Triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone in the presence of n-Bu4NN3 is a useful system for efficient conversion of tetrahydropyranyl (THP) ethers to their corresponding alkyl azides
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Triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone/tetrabutylammonium azide was used as an efficient system in conversion of tetrahydropyranyl ethers to corresponding alkyl azides. Copyright Taylor & Francis Inc.
- Akhlaghinia, Batool
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p. 1601 - 1604
(2007/10/03)
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