- A tandem reaction of 4-bromoalkyl aldehydes with sodium azide: Synthesis of 5,6,7,7a-tetrahydro-pyrrolo[1,2-d]-[1.2.3.4]oxatriazole
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5,6,7,7a-Tetrahydro-pyrrolo[1,2-d]-[1.2.3.4]oxatriazoles were synthesized through a nucleophilic substitution-cycloaddition tandem reaction of 4-bromoalkyl aldehydes with sodium azide.
- Ma, Yuan
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- Sequential synthesis of amino-1,4-naphthoquinone-appended triazoles and triazole-chromene hybrids and their antimycobacterial evaluation
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A general method for the synthesis of a library of hitherto unreported amino-1,4-naphthoquinone-appended triazoles was accomplished via a sequential three-component reaction of substituted N-propargylaminonaphthoquinones with variously substituted alkyl bromides/2-bromonaphthalene-1,4-dione and sodium azide in the presence of Et3N/CuI in water. Aminonaphthoquinone- appended iminochromene-triazole hybrid heterocycles were also synthesized from the amino-1,4-naphthoquinone-appended-1,2,3-triazolylacetonitriles. All the triazole hybrids were screened for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB). Among the triazoles, 2-(((1-benzyl-1H-1,2, 3-triazol-4-yl)methyl)(4-(trifluoromethyl)phenyl)amino)naphthalene-1,4-dione (7d) emerged as the most active one with IC50 = 1.87 μM, being more potent than the anti-TB drugs, cycloserine (6 times), pyrimethamine (20 times) and equipotent as the drug ethambutol (IC50 1.56 μM).
- Devi Bala, Balasubramanian,Muthusaravanan, Sivasubramanian,Choon, Tan Soo,Ashraf Ali, Mohamed,Perumal, Subbu
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- Tether influence on the binding properties of tRNALys 3 ligands designed by a fragment-based approach
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A small library of 1,5-triazole derivatives linking a diaminocyclopentadiol and aromatic ketones has been prepared and screened using NMR and fluorescent techniques against tRNALys3, the HIV reverse transcription primer. The comparis
- Moumne, Roba,Larue, Valery,Seijo, Bili,Lecourt, Thomas,Micouin, Laurent,Tisne, Carine
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- Synthesis of new bicarbazole-linked triazoles as non-cytotoxic reactive oxygen species (ROS) inhibitors
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Carbazole analogs 3 and 4 and a new library of bicarbazole-linked triazoles 6–11 were prepared via new synthetic methodology. Metal-catalyzed oxidative coupling reaction was utilized for the synthesis of bicarbazole acetylene 4 and different metals (Znsu
- Iqbal, Shazia,Khan, Maria A.,Ansari, Zulqarnain,Jabeen, Almas,Faheem, Aisha,Fazal-Ur-Rehman, Saba,Basha, Fatima Z.
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- A domino annulation approach to 3,4-diacylpyrrolo[1,2-a]pyrazines: decoration of pyrazine units
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A new one-pot, sequential three-component access to 3,4-diacylpyrrolo[1,2-a]pyrazine was achieved from the reaction of an α-haloketone, azide, andN-substituted pyrrole-2-carboxaldehyde under mild reaction conditions, through which a polysubstitution pattern on the pyrazine moiety of the scaffold was realized. The formation of multiple bonds (one C-C and two C-N) was enabled by this domino process involving thein situgeneration of α-iminoketones, intermolecular Mannich reaction, intramolecular imine formation, and aromatization. Construction of the relevant 3,4-diacylpyrazino[1,2-a]indole and further expansion of this chemical spaceviasynthetic elaboration of the resulting products were demonstrated as well. Preliminary biological screening of the synthesized derivatives against oral adenosquamous carcinoma cells (CAL-27) and triple negative human breast cancer cells (MDA-MB-231) led us to identify a potent hit compound (7o) having ~3 times strongerin vitroanticancer activity than that of the anticancer agent, capecitabine.
- Dagar, Anuradha,Kim, Ikyon,Namkung, Wan,Seo, Yohan
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- Synthesis of 2-substituted oxazoloquinazolinones
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[Figure not available: see fulltext.] The reaction of methyl 2-isothiocyanatobenzoate and 1-azido-3-(4-substituted phenyl)propan-2-ones in the presence of triphenyl phosphine in dioxane by heating produced tricyclic (Z)-2-(4-substituted benzylidene)-2,3-d
- Bobi?eva, Olga,Lo?a, Einārs
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- Indole-linked 1,2,3-triazole derivatives efficiently modulate COX-2 protein and PGE2 levels in human THP-1 monocytes by suppressing AGE-ROS-NF-kβ nexus
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Aims: AGEs augment inflammatory responses by activating inflammatory cascade in monocytes, and hence lead to vascular dysfunction. The current study aims to study a plausible role and mechanism of a new library of indole-tethered 1,2,3-triazoles 2-13 in A
- Aslam, Tooba,Basha, Fatima Z.,Choudhary, M. Iqbal,Iqbal, Shazia,Jahan, Humera,Khan, Maria Aqeel,Siddiqui, Nimra Naz
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- Visible-light-induced N-heterocyclic carbene mediated cascade transformation of N-alkenoxypyridinium salts
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While N-alkenoxypyridinium salts are widely used for the synthesis of α-functionalized ketones via umpolung strategy, such approaches are usually limited to special nucleophiles at high temperatures. Herein, we developed an alternative photoinduced N-heterocyclic carbene (NHC)- mediated functionalization of N-alkenoxypyridinium salts with various nucleophiles, including tetramethylammonium azide, secondary amines, aryl and alkyl thiols, and even the challenging C(sp3)-nucleophiles, under mild conditions. A cascade radical-radical coupling/nucleophilic substitution sequence was proposed, wherein the NHC enabled the formation of a photoactive electron donor-acceptor complex for α-iodo ketone synthesis.
- Chen, Fei,Chen, Xiangyu,Liu, Qiang,Sheng, He,Wang, Zhixiang
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supporting information
(2022/02/02)
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- Microwave mediated synthesis of 2-aminooxazoles
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A microwave mediated synthesis of 2-aminooxazoles at 150 °C was developed, providing products with a variety of functional groups. The reaction takes 5 min and provides product with a simple precipitation at moderate to good yields without the need for recrystallization or flash chromatography.
- Klug, Trevan,Cronin, Adam,O'Brien, Eli,Schioldager, Ryan,Johnson, Hunter,Gleason, Cameron,Schmid, Connor,Soderberg, Nathan,Manjunath, Aashrita,Liyanage, Duminda,Lazaro, Horacio,Kimball, Joshua J.,Eagon, Scott
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supporting information
(2021/12/14)
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- Interrupted CuAAC-Thiolation for the Construction of 1,2,3-Triazole-Fused Eight-Membered Heterocycles from O-/N-Propargyl derived Benzyl Thiosulfonates with Organic Azides
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A copper(I)-catalyzed interrupted click-sulfenylation of O-/N-propargyl benzyl thiosulfonates with organic azides has been disclosed. The unified CuAAC-thiolation provides a wide range of triazole-fused eight-membered heterocycles in good to high (51–94%) yields under mild reaction conditions. Moreover, a three-component reaction is also achieved involving O-/N-propargyl benzyl thiosulfonates, benzyl bromide, and sodium azide to deliver fused-triazoles in 61–74% yields. From a synthetic point of view, the present protocol has been demonstrated at gram-scale reactions. A plausible mechanism is also proposed based on experimental results and control experiments. (Figure presented.).
- Jannapu Reddy, Raju,Waheed, Md.,Haritha Kumari, Arram,Rama Krishna, Gamidi
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supporting information
p. 319 - 325
(2021/12/02)
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- Regioselective reduction of 1h-1,2,3-triazole diesters
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Regioselective reactions can play pivotal roles in synthetic organic chemistry. The reduction of several 1-substituted 1,2,3-triazole 4,5-diesters by sodium borohydride has been found to be regioselective, with the C(5) ester groups being more reactive towards reduction than the C(4) ester groups. The amount of sodium borohydride and reaction time required for reduction varied greatly depending on the N(1)-substituent. The presence of a β-hydroxyl group on the N(1)-substituent was seen to have a rate enhancing effect on the reduction of the C(5) ester group. The regioselective reduction was attributed to the lower electron densities of the C(5) and the C(5) ester carbonyl carbon of the 1,2,3-triazole, which were further lowered in cases involving intramolecular hydrogen bonding.
- Butler, Christopher R.,Bendesky, Justin,Schoffstall, Allen Milton
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- Discovery of triazolyl thalidomide derivatives as anti-fibrosis agents
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Fibrosis with excessive accumulation of extracellular matrix (ECM) often causes progressive organ dysfunction and results in many inflammatory and metabolic diseases, including systemic sclerosis, pulmonary fibrosis, advanced liver disease and advanced kidney disease. The store-operated calcium entry (SOCE) pathway and the related signaling pathway were both found to be the important routes for fibrogenesis. Our aim in this study was to discover novel compounds to inhibit fibrogenesis. A number of triazolyl thalidomide derivatives were synthesized and evaluated for their anti-fibrosis activities. Compounds 7b-e, 8c-d, 10a-b and 10e inhibited intracellular Ca2+ activation and showed no cytotoxicity. Among them, 6-{4-[(3-(1,3-dioxoisoindolin-2-yl)-2,6-dioxopiperidin-1-yl)methyl]-1H-1,2,3-triazol-1-yl}hexanoic acid (10e) with the most potent inhibitory effect was chosen for further examination. The results revealed that compound 10e, a SOCE inhibitor, reversed the migratory ability of TGF-β1-induced myofibroblasts, dedifferentiated myofibroblasts to fibroblasts due to cytoskeleton remodeling, and restrained myofibroblast activation by targeting Orai1 and TGF-β1/SMAD2/3 signaling pathways. The in silico study indicated that compound 10e, with the appropriate lipophilic carbon chain and carboxylic acid, showed a good drug-likeness model score. Conclusively, the SOCE inhibitor, compound 10e, is used as a promising lead compound for the development of a new treatment for fibrosis. This journal is
- Tang, Kai-Wei,Hsu, Wen-Li,Chen, Cheng-Ru,Tsai, Ming-Hsien,Yen, Chia-Jung,Tseng, Chih-Hua
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p. 3589 - 3599
(2021/03/03)
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- Design, Hemiysnthesis, crystal structure and anticancer activity of 1, 2, 3-triazoles derivatives of totarol
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A new series of diverse triazoles linked to the hydroxyl group of totarol were synthesized using click chemistry approach. The structures of these compounds were elucidated by HRMS, IR and NMR spectroscopy. The structure of compound 3 g was also confirmed by x-ray single crystal diffraction. The cytotoxicity of these compounds was evaluated by the MTT method against four cancer cell lines, including fibrosarcoma HT-1080, lung carcinoma A-549 and breast adenocarcinoma (MDA-MB-231 and MCF-7), and the results indicated that all compounds showed weak to moderate activities against all cancer cell lines with IC50 values ranging from 14.44 to 46.25 μM. On the basis of our research the structure–activity relationships (SAR) of these compounds were discussed. This work provides some important hints for further structural modification of totarol towards developing novel and highly effective anticancer drugs respectively. It is interesting to note that compound 3 g indicated a very significant cytotoxicity against HT-1080 and A-549 cell lines. The molecular docking showed that compound 3 g activated the caspase-3 and inhibited tubulin by forming stable protein–ligand complexes.
- Laamari, Yassine,Oubella, Ali,Bimoussa, Abdoullah,El Mansouri, Az-Eddine,Ketatni, El Mostafa,Mentre, Olivier,Ait Itto, My Youssef,Morjani, Hamid,Khouili, Mostafa,Auhmani, Aziz
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- Novel series of triazole containing coumarin and isatin based hybrid molecules as acetylcholinesterase inhibitors
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Novel series of coumarin-triazole and isatin-triazole hybrids were rationally designed, synthesized and biologically evaluated to check their inhibitory potential against acetylcholinesterase enzyme by using in vitro Ellman's method. Most of the hybrid compounds showed significant inhibition against the enzyme. Biological assay revealed that compound B-1 (among 4-hydroxycoumarin-triazole series) and compound AS-8 (from isatin-triazole series) possessed potent inhibitory activity against the AChE with the IC50 values of 110 ± 1.11 nM and 155 ± 1.65 nM, respectively. These active compounds (B-1 and AS-8) exhibited mixed mode of enzyme's inhibition which was confirmed through enzyme kinetic studies. Molecular docking studies were performed to understand the binding modes of these potent compounds within the active pocket of AChE enzyme by using Discovery studio. Furthermore, to predict the stability of the most prominent compound B-1 within the catalytic cavity of AChE, molecular dynamic simulations were performed for 5 ns and was found that ligand and protein complex is stable within their dynamic system. Therefore, these hybrids could be taken as effective lead candidates for further designing, development and optimization of new acetylcholinesterase inhibitors.
- Bedi, Preet Mohinder Singh,Bhagat, Kavita,Gulati, Harmandeep Kaur,Kaur, Arshmeet,Kumar, Nitish,Sharma, Aakriti,Singh, Atamjit,Singh, Harbinder,Singh, Jatinder Vir
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- Stereoselective synthesis of (Z)-1,3-bis(α,β-unsaturated carbonyl)-isoindolines from aldehydes and phenacyl azides under metal free conditions
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Here in the present manuscript, we report our observation of an unprecedented stereoselective synthesis of 2H-isoindolin-1,3-ylidenes from 2-(formylphenyl)acrylates and phenacylazide in the presence of piperidine. Unlike in our previous findings, in which
- Prasad, Budaganaboyina,Phanindrudu, Mandalaparthi,Nanubolu, Jagadeesh Babu,Kamal, Ahmed,Tiwari, Dharmendra Kumar
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supporting information
p. 9542 - 9545
(2021/09/28)
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- Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents
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We report that phenacyl azides are key compounds for a regiodivergent synthesis of valuable, functionalized imidazole (32–98% yield) and pyrimidine derivatives (45–88% yield), with a broad substrate scope, when using deep eutectic solvents [choline chloride (ChCl)/glycerol (1:2 mol/mol) and ChCl/urea (1:2 mol/mol)] as environmentally benign and non-innocent reaction media, by modulating the temperature (25 or 80 °C) in the presence or absence of bases (Et3N).
- Vitale, Paola,Cicco, Luciana,Cellamare, Ilaria,Perna, Filippo M.,Salomone, Antonio,Capriati, Vito
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supporting information
p. 1915 - 1923
(2020/08/17)
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- Usnic Acid Enaminone-Coupled 1,2,3-Triazoles as Antibacterial and Antitubercular Agents
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(+)-Usnic acid, a product of secondary metabolism in lichens, has displayed a broad range of biological properties such as antitumor, antimicrobial, antiviral, anti-inflammatory, and insecticidal activities. Interested by these pharmacological activities and to tap into its potential, we herein present the synthesis and biological evaluation of new usnic acid enaminone-conjugated 1,2,3-triazoles 10-44 as antimycobacterial agents. (+)-Usnic acid was condensed with propargyl amine to give usnic acid enaminone 8 with a terminal ethynyl moiety. It was further reacted with various azides A1-A35 under copper catalysis to give triazoles 10-44 in good yields. Among the synthesized compounds, saccharin derivative 36 proved to be the most active analogue, inhibiting Mycobacterium tuberculosis (Mtb) at an MIC value of 2.5 μM. Analogues 16 and 27, with 3,4-difluorophenacyl and 2-acylnaphthalene units, respectively, inhibited Mtb at MIC values of 5.4 and 5.3 μM, respectively. Among the tested Gram-positive and Gram-negative bacteria, the new derivatives were active on Bacillus subtilis, with compounds 18 [3-(trifluoromethyl)phenacyl] and 29 (N-acylmorpholinyl) showing inhibitory concentrations of 41 and 90.7 μM, respectively, while they were inactive on the other tested bacterial strains. Overall, the study presented here is useful for converting natural (+)-usnic acid into antitubercular and antibacterial agents via incorporation of enaminone and 1,2,3-triazole functionalities.
- Bangalore, Pavan K.,Vagolu, Siva K.,Bollikanda, Rakesh K.,Veeragoni, Dileep K.,Choudante, Pallavi C.,Misra, Sunil,Sriram, Dharmarajan,Sridhar, Balasubramanian,Kantevari, Srinivas
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- Chemo- and Enantioselective Oxidative α-Azidation of Carbonyl Compounds
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We report high-performance I+/H2O2 catalysis for the oxidative or decarboxylative oxidative α-azidation of carbonyl compounds by using sodium azide under biphasic neutral phase-transfer conditions. To induce higher reactivity especially for the α-azidation of 1,3-dicarbonyl compounds, we designed a structurally compact isoindoline-derived quaternary ammonium iodide catalyst bearing electron-withdrawing groups. The nonproductive decomposition pathways of I+/H2O2 catalysis could be suppressed by the use of a catalytic amount of a radical-trapping agent. This oxidative coupling tolerates a variety of functional groups and could be readily applied to the late-stage α-azidation of structurally diverse complex molecules. Moreover, we achieved the enantioselective α-azidation of 1,3-dicarbonyl compounds as the first successful example of enantioselective intermolecular oxidative coupling with a chiral hypoiodite catalyst.
- Hattori, Yuhei,Ishihara, Kazuaki,Sahara, Naoto,Tsukahara, Mayuko,Uyanik, Muhammet
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supporting information
p. 17110 - 17117
(2020/08/10)
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- Carbon isotope labeling of carbamates by late-stage [11C], [13C] and [14C]carbon dioxide incorporation
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A general procedure for the late-stage [11C], [13C] and [14C]carbon isotope labeling of cyclic carbamates is reported. This protocol allows the incorporation of carbon dioxide, the primary source of carbon-14 and carbon-11 radioisotopes, in a direct, cost-effective and sustainable manner. A disconnection/reconnection strategy, involving ring opening/isotopic closure, was also implemented.
- Del Vecchio, Antonio,Talbot, Alex,Caillé, Fabien,Chevalier, Arnaud,Sallustrau, Antoine,Loreau, Olivier,Destro, Gianluca,Taran, Frédéric,Audisio, Davide
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supporting information
p. 11677 - 11680
(2020/10/19)
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- Synthesis of Novel Heterocycles by Amide Activation and Umpolung Cyclization
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Herein, we report a metal-free synthesis of cyclic amidines, oxazines, and an oxazinone under mild conditions by electrophilic amide activation. This strategy features an unusual Umpolung cyclization mode and enables the smooth union of α-aryl amides and diverse alkylazides, effectively rerouting our previously reported α-amination transform.
- Maulide, Nuno,Riomet, Margaux,Roller, Alexander,Zhang, Haoqi
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supporting information
(2020/03/24)
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- C-H Insertion by Alkylidene Carbenes to Form 1,2,3-Triazines and Anionic [3 + 2] Dipolar Cycloadditions to Form Tetrazoles: Crucial Roles of Stereoelectronic and Steric Effects
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The synthesis of 1,2,3-triazines and bicyclic tetrazoles from α-azido ketones is described. The common intermediate generated from lithiated trimethylsilyldiazomethane and α-azido ketones diverges depending on the steric bulk of the substituents. The form
- Chen, Fa-Jie,Lin, Yongjia,Xu, Man,Xia, Yuanzhi,Wink, Donald J.,Lee, Daesung
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supporting information
p. 718 - 723
(2020/01/31)
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- Continuous-flow photo-induced decarboxylative annulative access to fused imidazole derivatives: Via a microreactor containing immobilized ruthenium
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Visible-light-driven continuous-flow decarboxylative annulation was achieved and used along with a microreactor containing immobilized ruthenium catalyst to construct valuable fused imidazole derivatives with high yields under an open atmosphere. Notably, this chemistry included the use of l-proline and α-azidochalcone as precursors of an α-amino radical and 2H-azirine via photo-induced decarboxylation and denitrogenation, respectively, to give the annulated imidazole derivatives as a result of the formation of two new C-N bonds. Moreover the novel, environmentally benign and efficient continuous-flow protocol was further improved by carrying out the reaction in a polydimethylsiloxane (PDMS) microreactor with immobilized Ru3+ under fluorescent or white LED light, enabling excellent yields (70-94%) at a reaction time (2 min) significantly shorter than that (16 h) of the batch protocol.
- Adiyala, Praveen Reddy,Jang, Seungwook,Vishwakarma, Niraj K.,Hwang, Yoon-Ho,Kim, Dong-Pyo
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supporting information
p. 1565 - 1571
(2020/03/26)
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- Concurrent Formation of N-H Imines and Carbonyl Compounds by Ruthenium-Catalyzed C-C Bond Cleavage of β-Hydroxy Azides
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A commercial cyclopentadienylrutenium dicarbonyl dimer ([CpRu(CO)2]2) efficiently catalyzes the formation of N-H imines and carbonyl compounds simultaneously from β-hydroxy azides via C-C bond cleavage under visible light. Density functional theory calculations for the cleavage reaction support the mechanism involving chelation of alkoxy azide species and liberation of nitrogen as the driving force. The synthetic utility of the reaction was demonstrated by a new amine synthesis promoted by chemoselective allylation of imine and synthesis of isoquinoline.
- Lee, Jeong Min,Bae, Dae Young,Park, Jin Yong,Jo, Hwi Yul,Lee, Eunsung,Rhee, Young Ho,Park, Jaiwook
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supporting information
p. 4608 - 4613
(2020/06/05)
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- Photocatalyst-Free Visible-Light Enabled Synthesis of Substituted Pyrroles from α-Keto Vinyl Azides
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An efficient photocatalyst-free visible light enabled synthesis of substituted pyrroles from α-keto vinyl azides (readily prepared via Knoevenagel condensation of phenacyl azides with 2-oxo-2H-chromene-3-carbaldehydes) was developed. The reaction proceeds
- Borra, Satheesh,Borkotoky, Lodsna,Newar, Uma Devi,Das, Babulal,Maurya, Ram Awatar
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supporting information
p. 3364 - 3368
(2020/07/13)
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- Metal-Free C-N or C-C Bond Cleavages of α-Azido Ketones: An Oxidative-Amidation Strategy for the Synthesis of α-Ketothioamides and Amides
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A novel metal-free oxidative-amidation strategy for the synthesis of α-ketothioamides and amides from α-azido ketones was developed. The C-H bond thionation of α-azido ketones with elemental sulfur could form α-ketothioacyl azide, which was then nucleophilically attacked by amines, causing the cleavage of the C-N bond to afford α-ketothioamides, while amides could be formed with the release of nitrogen gas and cyano anion in the presence of PhI(OAc)2 by selective C-C bond cleavage.
- Yu, Pei,Wang, Yuwei,Zeng, Zhigang,Chen, Yunfeng
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p. 14883 - 14891
(2019/11/11)
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- Streamlined Routes to Phenacyl Azides and 2,5-Diarylpyrazines Enabled by Deep Eutectic Solvents
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A Deep Eutectic Solvent like choline chloride/glycerol (1:2 mol mol–1) proved to be an effective, sustainable reaction medium to easily synthesize both phenacyl azides and symmetrical 2,5-diarylpyrazines of interest in pharmacology and in coordination chemistry. Notable features of our report include: (i) nucleophilic substitution reactions of α-halo carbonyl compounds to the corresponding phenacyl azides compatible with the eutectic mixture, (ii) the reduction of phenacyl azides to α-amino carbonyl compounds, which undergo spontaneous dimerisation/cyclisation/aromatisation in the same eutectic mixture to provide valuable pyrazines. Telescoped, one-pot, two-steps stoichiometric/catalytic processes have also been successfully developed to furnish 2,5-diarylpyrazines in up to 95 % yield.
- Vitale, Paola,Cicco, Luciana,Messa, Francesco,Perna, Filippo Maria,Salomone, Antonio,Capriati, Vito
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p. 5557 - 5562
(2019/08/21)
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- Preparation of chiral β-hydroxytriazoles in one-pot chemoenzymatic bioprocesses catalyzed by Rhodotorula mucilaginosa
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Chemoenzymatic strategies for the preparation of enantiopure β-hydroxytriazoles were designed. These and other related compounds are particularly relevant because of their antitubercular bioactivities and as β-adrenergic receptor blockers. The ability of
- Aguirre-Pranzoni, Celeste,Tosso, Rodrigo D.,Bisogno, Fabricio R.,Kurina-Sanz, Marcela,Orden, Alejandro A.
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p. 114 - 117
(2019/01/04)
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- A Bu4N[Fe(CO)3(NO)]-Catalyzed Hemetsberger–Knittel Indole Synthesis
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The nucleophilic Fe complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular amination of aryl vinyl azides to give the corresponding indole derivatives in good to excellent yields.
- Baykal, Aslihan,Plietker, Bernd
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supporting information
(2020/02/20)
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- Transition-Metal-Free One-Pot Tandem Synthesis of 3-Ketoisoquinolines from Aldehydes and Phenacyl Azides
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An efficient and transition-metal-free strategy for the synthesis of 3-keto-isoquinolines in one pot has been developed from the easily accessible 2-(formylphenyl)acrylates and phenacyl azides. Various substituted aldehydes and phenacyl azides were successfully employed in this transformation to furnish a variety 3-keto-isoquinolines in very good yields. A number of controlled experiments were conducted to postulate the reaction mechanism. Secondary functionalizations of 2-keto-isoquinolins were also performed to showcase the synthetic utility.
- Prasad, Budaganaboyina,Phanindrudu, Mandalaparthi,Tiwari, Dharmendra Kumar,Kamal, Ahmed
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p. 12334 - 12343
(2019/10/14)
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- Imidazolium-Based Ionic Network as a Robust Heterogeneous Catalyst in Synthesis of Phenacyl Derivatives
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A new imidazolium-based poly(ionic liquid) has been synthesized and used as a robust heterogeneous catalyst for the preparation of phenacyl derivatives by an SN2 reaction of different phenacyl bromides with a broad range of nucleophiles. The products are obtained in high yields under mild conditions. The catalyst can be recycled efficiently.
- Kakesh,Sayyahi,Badri,Tahanpesar
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p. 1218 - 1220
(2019/07/16)
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- Palladium-Catalyzed Aminocarbonylation Reaction to Access 1,2,3-Triazole-5-carboxamides Using Dimethyl Carbonate as Sustainable Solvent
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A simple and direct palladium-catalyzed aminocarbonylation of 5-iodo-1,2,3-triazoles backbone for the incorporation of an amide functional group is presented. The approach is based on the palladium catalyzed carbonylative coupling reaction of iodo-triazole with different amines employing formic acid and sulfuric acid as CO source (Morgan's reaction) to provide the 1,2,3-triazole-5-carboxamides in good to excellent yields. The important features of this methodology include short reaction time, high yields, the use of dimethyl carbonate as a sustainable solvent, and the use of efficient alternative source of carbon monoxide, avoiding pressurized cylinder. The methodology described herein for the synthesis of 1,4,5-trisubstituted 1,2,3-triazole-5-carboxamides, can offers an alternative path for functionalization of other heterocycles.
- de Albuquerque, Danilo Yano,de Moraes, Juliana R.,Schwab, Ricardo S.
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supporting information
p. 6673 - 6681
(2019/11/02)
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- Facile synthesis of 1,2,3-triazole-fused indolo- and pyrrolo[1,4]diazepines, DNA-binding and evaluation of their anticancer activity
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A facile synthetic strategy has been developed for the generation of structurally diverse N-fused heterocycles. The formation of fused 1,2,3-triazole indolo and pyrrolodiazepines proceeds through an initial Knoevenagel condensation followed by intramolecu
- Gour, Jitendra,Gatadi, Srikanth,Pooladanda, Venkatesh,Ghouse, Shaik Mahammad,Malasala, Satyaveni,Madhavi,Godugu, Chandraiah,Nanduri, Srinivas
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supporting information
(2019/10/05)
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- Design, synthesis, and anti-bacterial evaluation of triazolyl-pterostilbene derivatives
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Staphylococcus aureus resistance to current antibiotics has become the greatest global challenge facing public health. The development of new antimicrobial agents is urgent and important and is needed to provide additional therapeutic options. In our previous study, we found out that pterostilbene exhibited potent antibacterial activity, especially against methicillin-resistant Staphylococcus aureus (MRSA). According to previous studies, 1,2,3-triazole, with the characteristic of increasing the interaction with the target readily and enhancing water solubility, were widely used in the approved anti-bacterial drugs. Therefore, these results attract our interest to use the structure of pterostilbene as a scaffold for the hybrid 1,2,3-triazole moiety to develop a novel anti-MRSA infection agent. In this study, we demonstrated the design and synthesis of a series of triazolylpterostilbene derivatives. Among these compounds, compound 4d exhibited the most potent anti-MRSA activity with a minimum inhibitory concentration (MIC) value of 1.2-2.4 μg/mL and a minimum bactericidal concentration (MBC) value of 19.5-39 μg/mL. The structure-activity relationship and antibacterial mechanism were investigated in this study. Molecular docking studies were carried out to verify and rationalize the biological results. In this study, the results confirmed that our design could successfully increase the inhibitory activity and specificity against MRSA. Compound 4d could be used as a candidate for anti-bacterial agents and in depth vivo studies should be further investigated.
- Tang, Kai-Wei,Yang, Shih-Chun,Tseng, Chih-Hua
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- Visible-Light-Accelerated Copper(II)-Catalyzed Regio- and Chemoselective Oxo-Azidation of Vinyl Arenes
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The visible-light-accelerated oxo-azidation of vinyl arenes with trimethylsilylazide and molecular oxygen as stoichiometric oxidant was achieved. In contrast to photocatalysts based on iridium, ruthenium, or organic dyes, [Cu(dap)2]Cl or [Cu(dap)Cl2] were found to be unique for this transformation, which is attributed to their ability to interact with the substrates through ligand exchange and rebound mechanisms. CuII is proposed as the catalytically active species, which upon coordinating azide will undergo light-accelerated homolysis to form CuI and azide radicals. This activation principle (CuII-X→CuI+X.) opens up new avenues for copper-based photocatalysis.
- Hossain, Asik,Vidyasagar, Adiyala,Eichinger, Christian,Lankes, Christian,Phan, Jenny,Rehbein, Julia,Reiser, Oliver
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supporting information
p. 8288 - 8292
(2018/06/29)
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- Copper-Catalyzed Oxidative Difunctionalization of Terminal Unactivated Alkenes
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The copper(II)-promoted free-radical oxidative difunctionalization of terminal alkenes to access ketoazides by utilizing molecular oxygen has been reported. A series of styrene derivatives have been evaluated and were found to be compatible to give the desired difunctionalized products in moderate to good yields. The role of molecular oxygen both as an oxidant and oxygen atom source in this catalytic transformation has been unquestionably demonstrated by 18O-labeling studies and a radical mechanistic pathway involving the oxidative formation of azidyl radicals is also designed. This environment-friendly catalytic oxidative protocol can transform aldehyde to nitrile.
- Hussain, Muhammad Ijaz,Feng, Yangyang,Hu, Liangzhen,Deng, Qingfu,Zhang, Xiaohui,Xiong, Yan
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p. 7852 - 7859
(2018/05/30)
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- Visible-light-enabled oxyazidation of alkenes leading to α-azidoketones in air
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A new and facile visible-light-enabled method for the synthesis of α-azidoketones has been developed via oxyazidation of alkenes with TMSN3 in air at room temperature. A series of α-azidoketones could be easily and efficiently obtained in moder
- Wei, Wei,Cui, Huanhuan,Yue, Huilan,Yang, Daoshan
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supporting information
p. 3197 - 3202
(2018/07/29)
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- α-N-Heteroarylation and α-Azidation of Ketones via Enolonium Species
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Enolonium species, resulting from the umpolung of ketone enolates by Koser's hypervalent iodine reagents activated by boron trifluoride, react with a variety of nitrogen heterocycles to form α-aminated ketones. The reactions are mild and complete in 4-5 h. Additionally, α-azidation of the enolonium species takes place using trimethylsilyl azide as a convenient source of azide nucleophile.
- More, Atul A.,Pathe, Gulab K.,Parida, Keshaba N.,Maksymenko, Shimon,Lipisa, Yuriy B.,Szpilman, Alex M.
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p. 2442 - 2447
(2018/02/23)
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- A Straightforward Deracemization of sec-Alcohols Combining Organocatalytic Oxidation and Biocatalytic Reduction
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An efficient organocatalytic oxidation of racemic secondary alcohols, mediated by sodium hypochlorite (NaOCl) and 2-azaadamantane N-oxyl (AZADO), has been conveniently coupled with a highly stereoselective bioreduction of the intermediate ketone, catalyzed by ketoreductases, in aqueous medium. The potential of this one-pot two-step deracemization process has been proven by a large set of structurally different secondary alcohols. Reactions were carried out up to 100 mm final concentration enabling the preparation of enantiopure alcohols with very high isolated yields (up to 98 %). When the protocol was applied to the stereoisomeric rac/meso mixture of diols, these were obtained with very high enantiomeric excesses and diastereomeric ratios (95 % yield, >99 % ee, >99: 1 dr).
- Liardo, Elisa,Ríos-Lombardía, Nicolás,Morís, Francisco,González-Sabín, Javier,Rebolledo, Francisca
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supporting information
p. 3031 - 3035
(2018/06/27)
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- Site-Selective Conversion of Azido Groups at Carbonyl α-Positions to Diazo Groups in Diazido and Triazido Compounds
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This paper reports on the selective conversion of alkyl azido groups at the carbonyl α-position to diazo compounds. Through β-elimination of dinitrogen, followed by hydrazone formation/decomposition, α-azidocarbonyl moieties were transformed into α-diazo carbonyl groups in one step. As these reaction conditions do not involve aryl or general alkyl azides, site-selective conversions of di- and triazides were achieved. Through this method, the successive site-selective conjugation of the triazido molecule with three different components is demonstrated.
- Yokoi, Taiki,Tanimoto, Hiroki,Ueda, Tomomi,Morimoto, Tsumoru,Kakiuchi, Kiyomi
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p. 12103 - 12121
(2018/10/09)
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- Enantioselective separation of (±)-β-hydroxy-1,2,3-triazoles by supercritical fluid chromatography and high-performance liquid chromatography
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This paper reports the enantioseparation of β-hydroxy-1,2,3-triazole derivatives, which present a broad range of biological properties, by supercritical fluid chromatography (SFC) and high-performance liquid chromatography techniques (HPLC). Polysaccharid
- Alvarenga, Natália,Porto, André L.M.,Barreiro, Juliana Cristina
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p. 890 - 899
(2018/04/30)
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- 1,3,5-triazaspiro[5.5]undeca-2,4-dienes as selective Mycobacterium tuberculosis dihydrofolate reductase inhibitors with potent whole cell activity
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The emergence of multi- and extensively-drug resistant tubercular (MDR- and XDR-TB) strains of mycobacteria has limited the use of existing therapies, therefore new drugs are needed. Dihydrofolate reductase (DHFR) has recently attracted much attention as
- Yang, Xuan,Wedajo, Wassihun,Yamada, Yoshiyuki,Dahlroth, Sue-Li,Neo, Jason Jun-Long,Dick, Thomas,Chui, Wai-Keung
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p. 262 - 276
(2017/12/28)
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- Discovery of Natural Product Derived Labdane Appended Triazoles as Potent Pancreatic Lipase Inhibitors
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Obesity contributes to the genesis of many metabolic disorders including dyslipidemia, coronary heart disease (CHD), nonalcoholic fatty liver, type 2 diabetes, etc. Pancreatic lipase plays a vital role in food fat digestion and absorption. Therefore, to c
- Jalaja, Renjitha,Leela, Shyni G.,Valmiki, Praveen K.,Salfeena, Chettiyan Thodi F.,Ashitha, Kizhakkan T.,Krishna Rao, Venkata Rao D.,Nair, Mangalam S.,Gopalan, Raghu K.,Somappa, Sasidhar B.
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supporting information
p. 662 - 666
(2018/06/27)
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- One-pot synthesis of α-bromo- and α-azidoketones from olefins by catalytic oxidation with in situ-generated modified IBX as the key reaction
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Simple one-pot protocols for the syntheses of α-bromoketones and α-azidoketones starting from olefins have been developed by employing catalytic oxidation of the intermediary bromohydrins with in situ-generated modified IBX as the key reaction. The improved procedure involves initial formation of bromohydrin by the reaction of olefin with NBS in acetonitrile-water mixture (1:1) at rt followed by oxidation with in situ-generated 3,4,5,6-tetramethyl-2-iodoxybenzoic acid (TetMe-IBX), produced in catalytic amounts from 3,4,5,6-tetramethyl-2-iodobenzoic and Oxone. α-Bromoketones are further converted in the same pot to the corresponding α-azidoketones using NaN3/NaHCO3. The one-pot conversions are versatile for a variety of olefins that include cyclic as well as acyclic aliphatic olefins and electron-rich and electron-deficient styrenes. Chemoselective bromohydroxylation of electron-rich double bond and subsequent oxidation to the α-bromoketone is demonstrated for a substrate that contains both electron-rich and deficient double bonds.
- Chandra, Ajeet,Parida, Keshaba Nanda,Moorthy, Jarugu Narasimha
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p. 5827 - 5832
(2017/09/09)
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- In vitro α-glucosidase inhibition by non-sugar based triazoles of dibenzoazepine, their structure-Activity relationship, and molecular docking
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Background: α-Glucosidase inhibitors (AGIs) have been reported for their clinical potential against postprandial hyperglycemia, which is responsible for the risks associated with diabetes mellitus 2 and cardiovascular diseases (CVDs). Besides, a number of
- Khan, Maria A.,Javaid, Kulsoom,Batool, Farhana,Basha, Fatima Z.,Choudhary, Muhammad I.,Wadood, Abdul,Jamal, Alam,Fazal-Ur-Rehman, Saba
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p. 698 - 704
(2018/02/02)
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- Visible-Light-Promoted Metal-Free Aerobic Hydroxyazidation of Alkenes
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A highly efficient visible-light-promoted metal-free aerobic hydroxyazidation of alkenes has been developed. This protocol was operationally simple with broad substrate scope using relatively simple and readily available starting materials, such as alkene
- Yang, Bo,Lu, Zhan
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p. 8362 - 8365
(2017/12/08)
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- A α - azido carbonyl compound and its preparation method (by machine translation)
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The invention relates to a kind of α - azido carbonyl compound and its preparation method, in organic solvent, in order to end alkyne with trimethyl silicon nitrine as reaction raw material, in the copper catalysts and the persulfate oxidizing agent under the action of the common promotion, through the alkyne of double-functionalized α - azido obtained by reaction of a carbonyl compound. Azido free radical oxidation using air as the oxidizing agent in the terminal played a key role in the reaction process. The method substrate range widely, room temperature operation, mild reaction conditions, after treatment is simple and the yield of the product and high purity, is α - azido carbonyl compound has opened up a new synthetic route and method, and has good application potential and research value. (by machine translation)
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Paragraph 0074-0084; 0185-0189; 0191-0194; 0196-0199
(2017/09/02)
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- Stereoselective reduction of 2-azido-1-phenylethanone derivatives by whole cells of marine-derived fungi applied to synthesis of enantioenriched β-hydroxy-1,2,3-triazoles
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Several marine-derived fungi were evaluated by the bioreduction of 2-azido-1-phenylethanone 1, and the strains A. sydowii CBMAI 935 and M. racemosus CBMAI 847 were selected for the reduction of 2-azido-1-phenylethanone derivatives 2–4. Whole cells of A. s
- Alvarenga, Natália,Porto, André L. M.
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p. 388 - 396
(2017/10/06)
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- Leishmanicidal and cytotoxic activity of hederagenin-bistriazolyl derivatives
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Aiming to obtain new potent leishmanicidal and cytotoxic compounds from natural sources, the triterpene hederagenin was converted into several new 1,2,3-triazolyl derivatives tethered at C-23 and C-28. For this work hederagenin was isolated from fruits of
- Rodríguez-Hernández, Diego,Barbosa, Luiz C.A.,Demuner, Antonio J.,Nain-Perez, Amalyn,Ferreira, Sebasti?o R.,Fujiwara, Ricardo T.,de Almeida, Raquel M.,Heller, Lucie,Csuk, René
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supporting information
p. 624 - 635
(2017/10/13)
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- Self-assembled Triazole AIE-Active Nanofibers: Synthesis, Morphology, and Photophysical Properties
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A series of seven low molecular weight compounds containing triazole, pyridine-N-oxide, and one substituted aromatic ring linked together by heteroatoms containing spacers was synthesized by click chemistry reaction. The compounds were structurally characterized by FTIR, NMR, as well as single-crystal X-ray diffraction. Their morphologic, thermotropic, and photophysical properties were determined by dynamic light scattering, scanning electron microscopy, atomic force microscopy, polarized light microscopy, UV-vis, and photoluminescence spectroscopy. The triazole derivatives proved to have porous 3D supramolecular architectures determined by an extensive nonclassical hydrogen bonding network. They spontaneously crystallized into long nanofibers and exhibited typical molecular glass behavior, aggregation induced emission as well as crystallization induced emission enhancement.
- Marin, Luminita,Shova, Sergiu,Dumea, Carmen,Bicu, Elena,Belei, Dalila
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p. 3731 - 3742
(2017/07/12)
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- Integration of aqueous biphasic with magnetically recyclable systems: Polyethylene glycol-grafted Fe3O4 nanoparticles catalyzed phenacyl synthesis in water
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The present work trends to define an efficient phenacyl catalytic synthesis method employing a new nano-magnetite-supported organocatalyst. Polyethylene glycol (PEG) was bonded successfully onto silica coated ferrite and the resultant nanoparticles (PEG@SiO2@Fe3O4) characterized by fourier transform infrared spectroscopy (FT-IR), atomic force microscopy (AFM), thermal gravimetric analysis (TGA), vibrating sample magnetometry (VSM), energy dispersive X-ray analysis (EDAX) and X-ray diffraction (XRD) that exhibited a good catalytic activity in the reaction. The nanoparticles could be easily separated from the reaction mixture by an external magnet and reused in seven reaction cycles without significant loss of activity.
- Amini, Atefeh,Sayyahi, Soheil,Saghanezhad, Seyyed Jafar,Taheri, Narges
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- Catalytic transformation of esters of 1,2-azido alcohols into α-amido ketones
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The esters of 1,2-azido alcohols were transformed into α-amido ketones without external oxidants through the Ru-catalyzed formation of N-H imines with the liberation of N2 followed by intramolecular migration of the acyl moiety. A wide range of α-amido ketones were obtained, and one-pot transformation into the corresponding oxazoles (or a thiazole) was demonstrated.
- Kim, Yongjin,Pak, Han Kyu,Rhee, Young Ho,Park, Jaiwook
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supporting information
p. 6549 - 6552
(2016/06/01)
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- Synthesis and in vitro evaluation of dibenzoazepine triazole derivatives: A novel class of antileishmanial agents
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In the present study, a series of dibenzoazepine triazole derivatives (24-39) were synthesized and evaluated for their in vitro bioactivities including antiglycation, antibacterial, DPPH radical scavenging, urease inhibition, antileishmanial and immunomod
- Khan, Maria Aqeel,Saleem, Aliyan,Ghouri, Nida,Hameed, Abdul,Iqbal Choudhary,Basha, Fatima Z.
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p. 597 - 606
(2016/03/22)
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- Click chemistry inspired synthesis of piperazine-triazole derivatives and evaluation of their antimicrobial activities
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A series of novel piperazine-1,2,3-triazole derivatives, which entailed the bioisosteric replacement of the imidazole moiety and hybridization of two drug scaffolds was prepared by employing the regioselective copper (I)-catalysed azide-alkyne 1,3-dipolar cycloaddition reaction. The synthesized compounds were evaluated for antibacterial activities against Gram-negative (E. Coli and P. Putida), Gram-positive S. Aureus bacteria and fungicidal activities against F. oxysporum, F. gramillarium and F. monalliforme fungi. Compound 7ac′ exhibited moderate but promising antibacterial activity against Gram-negative bacteria and fungicidal activity against F. oxysporum and F. gramillarium.
- Khedar, Poonam,Pericherla, Kasiviswanadharaju,Singh, Rajnish Prakash,Jha, Prabhat Nath,Kumar, Anil
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p. 3117 - 3126
(2016/02/10)
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