- The azide-alkyne cycloaddition catalysed by transition metal oxide nanoparticles
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Colloidal nanoparticles of Earth-abundant, first-row transition metal oxides and sulfide, namely magnetite (Fe3O4), manganese and cobalt ferrite, (MnFe2O4, CoFe2O4), manganese(ii) oxide (Mn
- Molteni, Giorgio,Ferretti, Anna M.,Trioni, Mario Italo,Cargnoni, Fausto,Ponti, Alessandro
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- Unveiling Potent Photooxidation Behavior of Catalytic Photoreductants
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We describe a photocatalytic system that reveals latent photooxidant behavior from one of the most reducing conventional photoredox catalysts, N-phenylphenothiazine (PTH). This aerobic photochemical reaction engages difficult to oxidize feedstocks, such as benzene, in C(sp2)-N coupling reactions through direct oxidation. Mechanistic studies are consistent with activation of PTH via photooxidation and with Lewis acid cocatalysts scavenging inhibitors inextricably formed in this process.
- Targos, Karina,Williams, Oliver P.,Wickens, Zachary K.
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supporting information
p. 4125 - 4132
(2021/04/07)
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- Design, synthesis and antibacterial evaluation of novel 15-membered 11a-azahomoclarithromycin derivatives with the 1, 2, 3-triazole side chain
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Macrolides are widely prescribed in clinic to treat various respiratory tract infections. However, due to their inappropriate use, the prevalence of macrolide-resistant strains among clinical isolates has become a concern for public health. Therefore, nov
- Qin, Yinhui,Teng, Yuetai,Ma, Ruixin,Bi, Fangchao,Liu, Zhiyang,Zhang, Panpan,Ma, Shutao
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p. 321 - 339
(2019/07/18)
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- Hyperbranched polyethylenimine-supported copper(II) ions as a macroliganted homogenous catalyst for strict click reactions of azides and alkynes in water
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Loading hyperbranched polyethylenimine (PEI) with copper(II) ions leads to the formation of a new water-soluble metallodendritic polymer Cu(II)-PEI that has been found to effectively catalyze the clickable azide-alkyne [3 + 2] cycloaddition reactions in w
- Ben El Ayouchia, Hicham,ElMouli,Bahsis, Lahoucine,Anane,Laamari, Rachid,Gómez-García, Carlos J.,Julve, Miguel,Stiriba, Salah-Eddine
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- Catalytic Intermolecular Cross-Couplings of Azides and LUMO-Activated Unsaturated Acyl Azoliums
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An example for the catalytic synthesis of densely functionalized 1,2,3-triazoles through a LUMO activation mode has been developed. The protocol is enabled by intermolecular cross-coupling reactions of azides with in situ-generated α,β-unsaturated acyl az
- Li, Wenjun,Ajitha, Manjaly J.,Lang, Ming,Huang, Kuo-Wei,Wang, Jian
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p. 2139 - 2144
(2017/08/14)
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- Copper Acetate Catalyzed Regio-selective Synthesis of Substituted 1,2,3-Triazoles: A Versatile Azide–Alk-ene Cycloaddition/Oxidation Approach
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A copper acetate catalyzed oxidative cycloaddition reaction of benzyl and aryl azides with terminal and internal olefins that contain electron-withdrawing groups (COOR, CONH2, CN, CHO, COR) has been developed. The reaction employs air as the oxidant and does not require any base or additives to afford 1,4-disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles in good to excellent yields with high regioselectivity.
- Rohilla, Sandeep,Patel, Shyam Sunder,Jain, Nidhi
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p. 847 - 854
(2017/01/18)
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- Direct access to 1,4-disubstituted 1,2,3-triazoles through organocatalytic 1,3-dipolar cycloaddition reaction of α,β-unsaturated esters with azides
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DBU-catalyzed organocatalytic 1,3-dipolar cycloaddition reactions of α,β-unsaturated esters with azides have been developed. This strategy generates 1,4-disubstituted 1,2,3-triazoles in high yields with high regioselectivities. It is demonstrated that some of these products can be transformed into important pharmaceutical agents.
- Li, Wenjun,Zhou, Xiao,Luan, Yepeng,Wang, Jian
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p. 88816 - 88820
(2015/11/09)
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- Pressure-accelerated azide-alkyne cycloaddition: Micro capillary versus autoclave reactor performance
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Pressure effects on regioselectivity and yield of cycloaddition reactions have been shown to exist. Nevertheless, high pressure synthetic applications with subsequent benefits in the production of natural products are limited by the general availability o
- Borukhova, Svetlana,Seeger, Andreas D.,Nol, Timothy,Wang, Qi,Busch, Markus,Hessel, Volker
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p. 504 - 512
(2015/03/04)
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- 3-nitro- and 3-bromo-3-nitroacrylates in reactions with phenyl azide
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1,3-Dipolar cycloaddition of alkyl 3-nitro-and 3-bromo-3-nitroacrylates to phenyl azide gives regioisomeric alkyl 5(4)-nitro-1-phenyl-4,5-dihydro-1H-1,2,3- triazole-4(5)-carboxylates, the corresponding triazoles both with and without nitro group, and alky
- Berestovitskaya,Anisimova,Kataeva,Makarova,Berkova
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p. 1567 - 1575
(2008/03/14)
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- Antiplatelet properties of novel N-substituted-phenyl-1,2,3-triazole-4-acylhydrazone derivatives
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This paper describes the design, synthesis and pharmacological evaluation of new N-acylhydrazone (NAH) compounds, belonging to the N-substituted-phenyl-1,2,3-triazole-4-acylhydrazone class (2a-p). Classical heteroaromatic ring bioisosterism strategies wer
- Cunha, Anna C.,Figueiredo, Juliana M.,Tributino, Jorge L. M.,Miranda, Ana L. P.,Castro, Helena C.,Zingali, Russolina B.,Fraga, Carlos A. M.,De Souza, Maria Cecilia B. V.,Ferreira, Vitor F.,Barreiro, Eliezer J.
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p. 2051 - 2059
(2007/10/03)
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- Arylazide cycloaddition to methyl propiolate: DFT-based quantitative prediction of regioselectivity
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Several 1-(4-substituted)-phenyl-4- or 5-methoxycarbonyl-1,2,3-triazoles have been synthesized by 1,3-dipolar cycloaddition of the corresponding arylazides to methyl propiolate in carbon tetrachloride. The regioselectivity of these reactions cannot be rat
- Molteni, Giorgio,Ponti, Alessandro
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p. 2770 - 2774
(2007/10/03)
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- CYCLOADDITION DES METHYLAZIDE ET PHENYLAZIDE AU β-NITROSTYRENE ET AU NITROPROPENE HOMOLOGUE
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Phenylazide and methylazide reacts with title olefines and gives two isomeric triazoles without nitro group, and 4-nitro-1,2,3 triazole.The isomerisation of starting alkenes explains the formation of isomeric triazoles.Oxydation of amino-nitro-diazocompounds in equilibrium with 1,2,3 triazolines leads to 4-nitro-1,2,3 triazoles.
- Cailleux, P.,Piet, J. C.,Benhaoua, H.,Carrie, R.
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- KINETICS AND MECHANISM OF THE 1,3-DIPOLAR CYCLOADDITION OF PHENYL AZIDES TO METHYL 3-PYRROLIDINOACRYLATE
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Kinetics of cycloaddition of phenyl azides to methyl 3-pyrrolidinoacrylate (2) produced Hammett ρ=2.2.An Ea of 13.5 kcal mole-1 and ΔS* of -37.4 cal.K.-1 mole-1 were calculated for the cycloaddition of p-O2NC6H4N3 to 2.The cycloadditions are concerted, non-synchronous, and are controlled by LUMO (azide) - HOMO (dipolarophile) interactions.
- Al-Sader, Basil H.,Kadri, Mohamed
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p. 4661 - 4664
(2007/10/02)
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- ADDITION D' AZIDES A DES OLEFINES TRISUBSTITUEES PAR DES GROUPEMENTS ELECTROATTRACTEURS
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The reaction of benzyl, methyl and phenyl azide, with olefins substituted by three electron-withdrawing groups, has been studied.This reaction gives in certain cases only one triazoline (single orientation of the cycloaddition).In other cases, a mixture o
- Ouali, Mohand Said,Vaultier, Michel,Carrie, Robert
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p. 1821 - 1828
(2007/10/02)
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