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1.
A Cu-catalyzed interrupted click reaction for the synthesis of 3-perfluoroalkyl-substituted 1,2,4-triazinones is developed. The reaction between the terminal alkynes with azides and pentafluoropropionic or heptafluorobutyric anhydride proceeds smoothly to afford the corresponding pentafluoroethylated or heptafluoropropyled products in good yields. This protocol is applicable to various types of substrates including arylacetylenes and aliphatic azides having electron-rich and electron-deficient groups. The broad substrate scope and functional group tolerance of the reaction makes this approach a practical method for the synthesis of valuable 3-perfluoroalkyl-substituted 1,2,4-triazinones. Some of the title compounds showed fungicidal activity against cucumber downy mildew (CDM). 相似文献
2.
Sakellarios TrakossasEvdoxia Coutouli-Argyropoulou Dimitra J. Hadjipavlou-Litina 《Tetrahedron letters》2011,52(14):1673-1676
Copper-catalyzed 1,3-dipolar cycloaddition of propargyl and azidoethyl thymine and adenine derivatives afforded triazole nucleosides bearing one or two base moieties. A catalytic role of the adenine nucleus was observed and is explained through copper-adenine coordination in the intermediate copper acetylide-azide complex. The antioxidant activity of the obtained cycloadducts was tested. 相似文献
3.
Perumal Rajakumar Venkatesan KalpanaShanmugam Ganesan Pichai Maruthamuthu 《Tetrahedron letters》2011,52(44):5812-5816
Synthesis of novel dendrimers with benzothiazole as surface group and triazole as branching unit is achieved through click chemistry. The presence of more number of benzothiazole and triazole units increases the molar absorption coefficient and alters the fluorescence as well as electrochemical behaviors in the dendrimers. Dye-sensitized solar cell (DSSC) studies reveal that dendrimers with more number of benzothiazole and triazole groups exhibit better current generating capacity than the dendrimers with lesser number of benzothiazole and triazole groups. Dendrimer 2b shows the maximum current conversion efficiency (η) of 7.1%. 相似文献
4.
5.
An innovative synthetic pathway for the preparation of a new series of triazole-decorated dihydropyrimidinone peptidomimetics with skeletal α or β-amino acid residue is reported. The protocol involves two synthetic steps with an initial solvent-free and catalyst-free synthesis of propargylated dihydropyrimidinone precursors using Biginelli condensations. The subsequent cycloaddition reactions of pyrimidinone alkynes with small peptide like azides prepared from Ugi or alternate Mannich type multi-component reactions afforded the triazole decorated pyrimidinone peptide conjugates in excellent yield with high regio and stereospecificities. In total, a scaffold diversity contains 11 new pyrimidinone alkynes and 18 new pyrimidinone peptidomimetics were introduced into the chemical space. 相似文献
6.
Stéphanie Durot 《Tetrahedron》2008,64(36):8496-8503
The Cu(I)-catalyzed dipolar cycloaddition of azides and terminal alkynes (‘click’ chemistry) has been used as a mild and efficient stoppering reaction for the preparation of new copper(I)-complexed rotaxanes. 相似文献
7.
Changwei ShaoRui Zhu Sheng LuoQun Zhang Xinyan Wang Yuefei Hu 《Tetrahedron letters》2011,52(29):3782-3785
A simple combination of Cu2O and PhCO2H ‘on H2O’ has been developed as a highly practical and efficient catalytic system for copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC). It not only provides a further evidence for the strategy of carboxylic acids-promoted CuAAC, but also offers significant advantages to CuAAC because Cu2O is one of the most stable and cheapest Cu(I) sources; PhCO2H is one of the structurally simplest bidentate ligands; and water is the most ‘green’ solvent. 相似文献
8.
Rong-Xing Yao Lei Kong Zeng-Shen Yin Feng-Ling Qing 《Journal of fluorine chemistry》2008,129(10):1003-1010
The synthesis and characterization of a novel class of linear aromatic ether polymers containing perfluorocyclobutyl and triazole unites is described. These polymers were prepared from the click chemistry (the copper-catalyzed Huisgen's 1,3-dipolar cycloaddition) of new monomer 1,2-bis(4-azidomethylphenoxy) perfluorocyclobutane and bisethynyl compounds. 相似文献
9.
A series of triazole bridged BODIPY-conjugates were synthesized under click reaction conditions. The 3-azido BODIPY was generated in situ by treating 3-bromo BODIPY with NaN3 in CH3CN at room temperature for 60 min and reacted with appropriate ethynyl containing chromophore/redox active unit, such as ferrocene, BODIPY, Zn(II) porphyrin, 21,23-dithiaporphyrin, BF2-smaragdyrin in the presence of CuI/DIPEA in THF/CH3CN solvent. The conjugates were purified by column chromatography and obtained pure compounds in 45–50% yields. The conjugates were characterized by HR-MS, 1D, 2D, 19F and 11B NMR and X-ray crystallography for BODIPY-ferrocene conjugate. Absorption and electrochemical studies showed features of both the moieties present in the conjugates and also support interaction between the two moieties in the conjugates. The fluorescence studies supported an efficient energy transfer from BODIPY unit to BF2-smaragdyrin unit in BODIPY–BF2-smaragdyrin conjugate but the energy transfer was not efficient in BODIPY–Zn(II) porphyrin and BODIPY–21,23-dithiaporphyrin conjugates. 相似文献
10.
Sharpless modified Huisgen’s [2+3] cycloaddition of azide and acetylenic derivatives was employed as an efficient and simple method to conjugate azabicycloalkane amino acids, mimics of a homoSer-Pro dipeptide, with biologically relevant partners. 相似文献
11.
Takeshi Fujita Masahiro Hattori Masaaki Matsuda Ryutaro Morioka Tanner C. Jankins Masahiro Ikeda Junji Ichikawa 《Tetrahedron》2019,75(1):36-46
Ketones and imines bearing a 2-(trifluoromethyl)allylic moiety successfully underwent nucleophilic 5-endo-trig cyclization via their metal enolates and enamides. O- or N-Cyclization proceeded exclusively in each case to afford the corresponding five-membered heterocycles with both exo-difluoromethylene and exo-alkylidene units. On treatment with potassium hexamethyldisilazide (KHMDS) or lithium diisopropylamide (LDA), 2-(trifluoromethyl)allylic ketones or imines provided the corresponding tetrahydrofurans or pyrrolidines bearing a Z-alkylidene group with perfect or substantial stereoselectivity, respectively. 相似文献
12.
Mohamed R. Shaaban 《Journal of fluorine chemistry》2008,129(12):1156-1161
4,4,4-Trifluoro-1-(thien-2-yl)butane-1,3-dione (1) reacts with 5-aminopyrazole, 1,2,4-aminotriazole and 2-aminobenzimidazole derivatives, in the presence of triethylorthoformate under pressurized microwave irradiation to afford the corresponding trifluoromethyl derivatives of pyrazolo[1,5-a]pyrimidine, 1,2,4-triazolo[1,5-a]pyrimidine, and pyrimido[1,2-a]benzimidazoles. Also, compound 1 couples readily with azole diazonium salts to give pyrazolo[5,1-c]triazine, benzimidazo[5,1-c]1,2,4-triazine, and triazolo[3,4-c]1,2,4-triazine derivatives incorporating trifluoromethyl group. 相似文献
13.
Pierangelo Fabbrizzi Francesca Bianchini Gloria Menchi Silvia Raspanti Antonio Guarna Andrea Trabocchi 《Tetrahedron》2014
Fragment-based drug discovery is a valuable tool in hit identification, as well as the combination of different small fragments showing a minimal binding activity against biological receptors or enzymes to give merged hits. A high number of fragments on the same scaffold improve the probability to find a candidate showing single- or multi-target affinities. A rapid and versatile approach for synthesizing libraries of densely fragment-functionalized scaffolds is reported. Many fragments were assembled in few steps around a triazole ring starting from amino alcohols and other readily available building blocks. A binding assay against integrin αvβ3 was used as a test-bed in order to demonstrate the potential of such an approach in hit discovery strategies. 相似文献
14.
《Tetrahedron: Asymmetry》2006,17(18):2654-2658
A Schiff’s base ligand with a trifluoromethyl carbinol moiety was synthesized, and a structure of the active complex for asymmetric induction on the reaction of diethylzinc with aldehydes is proposed. 相似文献
15.
A concise protocol for the synthesis of pyrimidinone/indole functionalized hybrid peptide macrocycles with varying ring size is described. The precursors of the macrocycles were obtained from the post reaction modification of multicomponent reaction products and were cyclized via copper (I) catalyzed [3?+?2] azide-alkyne cycloaddition. The macrocycles showed excellent inhibitory property towards CDK2 protein which is responsible for a variety of cancers and were also showed excellent cytotoxicity against human breast cancer cell line MCF-7. 相似文献
16.
The novel (S)-BINOL-based sensor 1 incorporating triazole moieties could be obtained by click reaction. The results show that 1 can exhibit excellent fluorescence response behaviors toward Hg2+ (selective switching-off) and Ag+ (selective switching-on) without interference from other metal ions, which functions as a molecular switch. This work can expand the application of click reaction in design and synthesis of the novel fluorescence sensor molecules. 相似文献
17.
Weiguang Yang Dayun Huang Xiaobao Zeng Jianlan Zhang Xinyan Wang Yuefei Hu 《Tetrahedron》2019,75(3):381-386
A highly reactive intermediate N-sulfonyl acetylketenimine was generated from an ynone-participated CuAAC/ring-opening method. Its unique structure allowed it to react with aryl carboxylic acids to give N-aroylsulfonamides via a novel Mumm-type rearrangement. 相似文献
18.
A copper-catalyzed aerobic oxidative CN bond cleavage reaction was developed for the synthesis of 4-substituted-NH-1,2,3-triazoles. Diverse β-ketotriazoles derivatives, which are the starting materials for the aerobic oxidative CN bond cleavage reaction, were prepared from nine aryl and seven alkyl alkynes and α-azidoacetophenone by a copper(I)-catalyzed [3 + 2]cycloaddition reaction. The aerobic oxidation of α-(1,2,3-triazol-1-yl)acetophenones using a catalytic amount of copper(II) acetate in the presence oxygen under neutral conditions gave the title compounds in high yield. 相似文献
19.
Dr. Chunwei Dong Dr. Ren-Wu Huang Dr. Arunachalam Sagadevan Dr. Peng Yuan Dr. Luis Gutiérrez-Arzaluz Dr. Atanu Ghosh Saidkhodzha Nematulloev Badriah Alamer Prof. Dr. Omar F. Mohammed Prof. Dr. Irshad Hussain Prof. Dr. Magnus Rueping Prof. Dr. Osman M. Bakr 《Angewandte Chemie (International ed. in English)》2023,62(37):e202307140
Elucidating single-atom effects on the fundamental properties of nanoparticles is challenging because single-atom modifications are typically accompanied by appreciable changes to the overall particle's structure. Herein, we report the synthesis of a [Cu58H20PET36(PPh3)4]2+ ( Cu58 ; PET: phenylethanethiolate; PPh3: triphenylphosphine) nanocluster—an atomically precise nanoparticle—that can be transformed into the surface-defective analog [Cu57H20PET36(PPh3)4]+ ( Cu57 ). Both nanoclusters are virtually identical, with five concentric metal shells, save for one missing surface copper atom in Cu57 . Remarkably, the loss of this single surface atom drastically alters the reactivity of the nanocluster. In contrast to Cu58 , Cu57 shows promising activity for click chemistry, particularly photoinduced [3+2] azide-alkyne cycloaddition (AAC), which is attributed to the active catalytic site in Cu57 after the removal of one surface copper atom. Our study not only presents a unique system for uncovering the effect of a single-surface atom modification on nanoparticle properties but also showcases single-atom surface modification as a powerful means for designing nanoparticle catalysts. 相似文献
20.
Kamil KopeckyVeronika Novakova Miroslav MiletinRadim Ku?era Petr Zimcik 《Tetrahedron》2011,67(33):5956-5963
New unsymmetrical zinc azaphthalocyanine (AzaPc) was synthesized using statistical condensation of two precursors. Postsynthetic modifications led to incorporation of azide group that efficiently underwent Cu(I)-catalyzed azide/alkyne 1,3-dipolar cycloaddition with terminal alkyne on a solid phase. The modified solid phase was then used for synthesis of oligodeoxyribonucletides labeled with AzaPc. DNA hybridization assays confirmed high quenching efficiency (QE>96%) of zinc AzaPc quencher with six different fluorophores ranging in emission maxima from 517 nm to 701 nm (FAM, HEX, Cy3, Cy3.5, Cy5, and Cy5.5). 相似文献