- 1-Disulfo-[2,2-bipyridine]-1,1-diium chloride ionic liquid as an efficient catalyst for the green synthesis of 5-substituted 1H-tetrazoles
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A simple, green and efficient method has been developed for the synthesis of 5-substituted 1H-tetrazole derivatives through [2+3] cycloaddition reaction in good to excellent yields between various benzonitriles and sodium azide. For this purpose, 1-disulfo-[2,2-bipyridine]-1,1-diium chloride ([BiPy](HSO3)2Cl2) system as an ionic liquid catalyst have been extended for the construction of these valuable products. This procedure has significant advantages, including using ethylene glycol as a green solvent. The other advantages of this method are inexpensive and ease the preparation of the catalyst, mild reaction conditions, green reaction medium, easy workup, short reaction time, and simple experimental process.
- Aali, Elaheh,Gholizadeh, Mostafa,Noroozi-Shad, Nazanin
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- Fe3O4@L-lysine-Pd(0) organic–inorganic hybrid: As a novel heterogeneous magnetic nanocatalyst for chemo and homoselective [2 + 3] cycloaddition synthesis of 5-substituted 1H-tetrazoles
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An efficient and sustainable synthetic protocol has been presented to synthesis and 5-substituted 1H-tetrazole privileged heterocyclic substructures. The synthetic protocol involves two-component reaction between aryl nitriles and NaN3 in water using complex of L-lysine-palladium nanoparticles (NPs) modified Fe3O4 nanoparticles as magnetically separable, recyclable, and reusable heterogeneous catalyst. Magnetically retrievable L-lysine-Pd(0) modified Fe3O4 nanoparticles were applied in [2 + 3] cycloaddition synthesis of 5-substituted 1H-tetrazoles. The advantages of this strategy include easy recovery and efficient reusability of the expensive Pd NPs, obtaining high yields of [2 + 3] cycloaddition, short reaction times, and all of the reported synthetic strategies are being performed in water as green solvent for a wide range of substrates.
- Ashraf, Muhammad Aqeel,Liu, Zhenling,Li, Cheng,Zhang, Dangquan
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- The mineral alum: an effective and low-cost heterogeneous catalyst for the successful synthesis of 5-substituted-1H-tetrazoles
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A simple, efficient, and green procedure for the synthesis of 5-substituted-1H-tetrazoles via [3 + 2] cycloaddition reaction of nitriles with sodium azide is described. The reaction was catalyzed by natural and mesoporous alum nanoparticles (NPs) in DMSO
- Karimian, Azam,Emarloo, Nahid,Salari, Samira
-
-
- INHIBITORS OF α-AMINO-β-CARBOXYMUCONIC ACID SEMIALDEHYDE DECARBOXYLASE
-
The present disclosure discloses compounds capable of modulating the activity of α-amino-β-carboxymuconic acid semialdehyde decarboxylase (ACMSD), which are useful for the prevention and/or the treatment of diseases and disorders associated with defects in NAD+ biosynthesis, e.g., metabolic disorders, neurodegenerative diseases, chronic inflammatory diseases, kidney diseases, and diseases associated with ageing. The present application also discloses pharmaceutical compositions comprising said compounds and the use of such compounds as a medicament.
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-
Paragraph 00491
(2020/06/10)
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- One-Pot Suzuki-Hydrogenolysis Protocol for the Modular Synthesis of 2,5-Diaryltetrazoles
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2,5-Diaryltetrazoles are a diverse range of compounds of considerable interest within the field of photochemistry as a valuable precursor of the nitrile imine 1,3-dipole. Current literature approaches toward this heterocycle remain unsuitable for the prac
- Bertrand, Sophie,Jamieson, Craig,Livingstone, Keith
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p. 7413 - 7423
(2020/07/07)
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- Novel Hybrid Thioamide Ligand Supported Copper Nanoparticles on SBA-15: A Copper Rich Robust Nanoreactor for Green Synthesis of Triazoles and Tetrazoles in Water Medium
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Abstract: In this work, a new thioamide based ligand with reductive nature was designed for modification of mesoporous SBA-15. For this purpose, the channels of SBA-15 were modified with Tris(2-aminoethyl)amine (TAEA) groups and then reacted with S8 and phenyl acetylene to form thioamide groups via Willgerodt-Kindler reaction. This porous material proved to be an effective host for the immobilization of inexpensive Cu(II) ions. The catalytically active Cu(I) species were generated automatically due to the reductive nature of thioamide modified surface of catalyst without use of any toxic reducing agents. The well stabilized Cu(I) species into the nano-channels of SBA-15 were used for synthesis of various triazoles from sodium azide, phenyl acetylene and alkyl/benzyl halides or alkyl epoxides and various tetrazoles from sodium azide and aryl/alkyl nitriles under green mild aqueous reaction conditions. This catalytic system was used for 9 and 11 consecutive runs for synthesis of triazoles and tetrazoles, respectively. Graphic Abstract: [Figure not available: see fulltext.]
- Pourhassan, Fatemeh,Eshghi, Hossein
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p. 1287 - 1300
(2019/11/21)
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- Methionine-Coated Fe3O4 Nanoparticles: An Efficient and Reusable Nanomagnetic Catalyst for the Synthesis of 5-Substituted 1H-Tetrazoles
-
Abstract: Methionine-coated Fe3O4 nanoparticles, a magnetically reusable and environmentally friendly heterogeneous catalyst, was synthesized. The new catalyst was characterized by FT-IR spectra, XRD, SEM, and EDX analysis and was us
- Abbasi, R.,Karimian, A.,Namvar-Mhaboub, M.
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p. 1646 - 1653
(2020/10/22)
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- Fragment based drug design and diversity-oriented synthesis of carboxylic acid isosteres
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The medicinal chemist toolbox is plenty of (bio)isosteres when looking for a carboxylic acid replacement. However, systematic assessment of acid surrogates is often time consuming and expensive, while prediction of both physicochemical properties (logP and logD) as well as acidity would be desirable at early discovery stages for a better analog design. Herein in this work, to enable decision making on a project, we have synthesized by employing a Diversity-Oriented Synthetic (DOS) methodology, a small library of molecular fragments endowed with acidic properties. By combining in-silico and experimental methodologies these compounds were chemically characterized and, particularly, with the aim to know their physicochemical properties, the aqueous ionization constants (pKa), partition coefficients logD and logP of each fragment was firstly estimated by using molecular modeling studies and then validated by experimental determinations. A face to face comparison between data and the corresponding carboxylic acid might help medicinal chemists in finding the best replacement to be used. Finally, in the framework of Fragment Based Drug Design (FBDD) the small library of fragments obtained with our approach showed good versatility both in synthetic and physico-chemical properties.
- Alunno, Manuel,Camaioni, Emidio,Carotti, Andrea,Ferri, Martina,Greco, Francesco Antonio,Liscio, Paride,Macchiarulo, Antonio,Mammoli, Andrea,Saluti, Giorgio,Sardella, Roccaldo
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-
- A robust and recyclable ionic liquid-supported copper(II) catalyst for the synthesis of 5-substituted-1H-tetrazoles using microwave irradiation
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Abstract: A novel and robust ionic liquid-supported copper(II) catalyst has been developed and explored for the efficient synthesis of 5-substituted-1H-tetrazoles using microwave irradiation. The ionic liquid-supported catalyst facilitated the efficient isolation of tetrazole products with high purity by simple extraction with organic solvent. Recovered ionic liquid-supported copper(II) catalyst could be recycled for three times for the synthesis of tetrazole products with high purity. This synthetic protocol offers a very clean, convenient, and microwave-assisted environment-friendly method for the efficient synthesis of 5-substituted-1H-tetrazoles with high yield. Graphic abstract: [Figure not available: see fulltext.].
- Padmaja,Chanda, Kaushik
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p. 1307 - 1317
(2019/11/14)
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- Tandem magnetization and post-synthetic metal ion exchange of metal–organic framework: Synthesis, characterization and catalytic study
-
For the first time, metal-exchange in a magnetic metal–organic framework (MOF) via tandem magnetization and post-synthetic modification has been developed. The new magnetic mixed-metal metal–organic framework nanocomposite, CoFe2O4/[
- Yadollahi, Mahtab,Hamadi, Hosein,Nobakht, Valiollah
-
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- Discovery, synthesis and characterization of a series of (1-alkyl-3-methyl-1H-pyrazol-5-yl)-2-(5-aryl-2H-tetrazol-2-yl)acetamides as novel GIRK1/2 potassium channel activators
-
The present study describes the discovery and characterization of a series of 5-aryl-2H-tetrazol-3-ylacetamides as G protein-gated inwardly-rectifying potassium (GIRK) channels activators. Working from an initial hit discovered during a high-throughput screening campaign, we identified a tetrazole scaffold that shifts away from the previously reported urea-based scaffolds while remaining effective GIRK1/2 channel activators. In addition, we evaluated the compounds in Tier 1 DMPK assays and have identified a (3-methyl-1H-pyrazol-1-yl)tetrahydrothiophene-1,1-dioxide head group that imparts interesting and unexpected microsomal stability compared to previously-reported pyrazole head groups.
- Sharma, Swagat,Kozek, Krystian A.,Abney, Kristopher K.,Kumar, Sushil,Gautam, Nagsen,Alnouti, Yazen,David Weaver,Hopkins, Corey R.
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supporting information
p. 791 - 796
(2019/02/06)
-
- Efficient synthesis of tetrazole hemiaminal silyl ethers via three-component hemiaminal silylation
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An efficient route to construct 2,5-disubstituted tetrazole hemiaminal silyl ethers via one-pot three-component hemiaminal silylation of 5-substituted tetrazoles, aldehydes, and silyl triflates was developed. Diverse 2,5-disubstituted tetrazole hemiaminal silyl ethers were obtained with 37?:?63->99?:?1 regioisomeric ratios. The regioselectivities of this reaction were significantly affected by steric hindrance and the conjugation effects of substitutions on the 5-position of tetrazoles.
- Xie, Ming-Sheng,Cheng, Xuan,Chen, Yang-Guang,Wu, Xiao-Xia,Qu, Gui-Rong,Guo, Hai-Ming
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supporting information
p. 6890 - 6894
(2018/10/17)
-
- Facile one-pot preparation of 5-aryltetrazoles and 3-arylisoxazoles from aryl bromides
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The successive treatment of aryl bromides with n-BuLi, DMF, hydroxylamine hydrochloride, and finally diphenylphosphoryl azide provided efficiently the corresponding 5-aryltetrazoles in good to moderate yields. Similarly, the successive treatment of aryl bromides with n-BuLi, DMF, hydroxylamine hydrochloride, and finally diethyl acetylenedicarboxylate and Oxone provided efficiently the corresponding diethyl 3-arylisoxazole-4,5-dicarboxylates in good to moderate yields. Aromatic aldoximes are the key intermediates in both reactions, and 5-aryltetrazoles and 3-arylisoxazoles could be obtained from aryl bromides in one pot under transition-metal-free conditions.
- Kobayashi, Eiji,Togo, Hideo
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p. 4226 - 4235
(2018/07/06)
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- α-Amino-β-carboxymuconate-?-semialdehyde Decarboxylase (ACMSD) Inhibitors as Novel Modulators of de Novo Nicotinamide Adenine Dinucleotide (NAD+) Biosynthesis
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NAD+ has a central function in linking cellular metabolism to major cell-signaling and gene-regulation pathways. Defects in NAD+ homeostasis underpin a wide range of diseases, including cancer, metabolic disorders, and aging. Although the beneficial effects of boosting NAD+ on mitochondrial fitness, metabolism, and lifespan are well established, to date, no therapeutic enhancers of de novo NAD+ biosynthesis have been reported. Herein we report the discovery of 3-[[[5-cyano-1,6-dihydro-6-oxo-4-(2-thienyl)-2-pyrimidinyl]thio]methyl]phenylacetic acid (TES-1025, 22), the first potent and selective inhibitor of human ACMSD (IC50 = 0.013 μM) that increases NAD+ levels in cellular systems. The results of physicochemical-property, ADME, and safety profiling, coupled with in vivo target-engagement studies, support the hypothesis that ACMSD inhibition increases de novo NAD+ biosynthesis and position 22 as a first-class molecule for the evaluation of the therapeutic potential of ACMSD inhibition in treating disorders with perturbed NAD+ supply or homeostasis.
- Pellicciari, Roberto,Liscio, Paride,Giacchè, Nicola,De Franco, Francesca,Carotti, Andrea,Robertson, Janet,Cialabrini, Lucia,Katsyuba, Elena,Raffaelli, Nadia,Auwerx, Johan
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p. 745 - 759
(2018/02/17)
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- Synthesis, Structure, and Anti-influenza Activity of 2-(Adamantan-1-yl)-5-aryl-1,3,4-oxadiazoles and 2-(Adamantan-1-yl)-5-aryltetrazoles
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Two series of new adamantyl derivatives of polynitrogen heterocycles, 2-(adamantan-1-yl)-5-aryl- 1,3,4-oxadiazoles and 2-(adamantan-1-yl)-5-aryl-2H-tetrazoles, have been synthesized, and their structure has been determined by NMR spectroscopy, mass spectr
- Seliverstova,Suslonov,Zarubaev,Trifonov
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p. 633 - 638
(2018/06/12)
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- OXOPYRIDINE DERIVATIVES USEFUL AS AMINOCARBOXYMUCONATE SEMIALDEHYDE DECARBOXYLASE (ACMSD) INHIBITORS
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The present invention is related to a compound represented by the following structural formula: The present invention is also related a method of treating a subject with a disease which can be ameliorated by inhibition of aminocarboxymuconate semialdehyde decarboxylase (ACMSD).
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Page/Page column 78; 79
(2018/07/29)
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- Process for the preparation of quinoline based ionic fluoride salts (QUFS)
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The current invention relates to ionic liquid preparation and their application in organic synthesis. More specifically, the present invention relates to the quinoline based ionic liquids having fluoride counter anion and their applications in click chemi
- -
-
Page/Page column 4; 12; 13
(2017/05/31)
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- Choline chloride–ZnCl2: Recyclable and efficient deep eutectic solvent for the [2+3] cycloaddition reaction of organic nitriles with sodium azide
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Herein we report first time choline chloride–zinc chloride based deep eutectic solvent is a green and efficient reaction medium for the [2+3] cycloaddition reaction of organic nitriles with sodium azide to afford the corresponding 5-substituted 1H-tetrazo
- Padvi, Swapnil A.,Dalal, Dipak S.
-
supporting information
p. 779 - 787
(2017/04/06)
-
- Cu(II) immobilized on Fe3O4@APTMS-DFX nanoparticles: An efficient catalyst for the synthesis of 5-substituted 1: H -tetrazoles with cytotoxic activity
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Cu(ii) immobilized on deferasirox loaded amine functionalized magnetic nanoparticles (Cu(ii)/Fe3O4@APTMS-DFX) as a novel magnetically recyclable heterogeneous catalyst is able to catalyze the [3 + 2] cycloaddition reactions of various organic nitriles with sodium azide. Using this method, a series of 5-substituted-1H-tetrazoles under mild conditions in DMSO were prepared. The reaction involves mild reaction conditions with efficient transformation capability. The developed catalyst could be easily separated by applying an external magnetic field. Furthermore, it could be recycled for 5 runs with negligible leaching of copper from the surface of the catalyst. The catalyst was characterized by various techniques such as FT-IR, TGA, VSM, SEM-EDX, and ICP-OES. Several derivatives of 1H-tetrazoles were prepared using this catalyst, and their structures were confirmed using different techniques. Then, the synthesized anthraquinones were evaluated for their cytotoxicity against several cell lines including MCF-7, MAD-MD-231, HT-29, HeLa, neuro-2a and L-929. The results obtained from the MTT assay revealed that the 6 derivatives exhibited a high level of cytotoxicity. In order to determine the cytotoxicity mechanism, 2 derivatives with the highest cytotoxic activity were selected, and an apoptosis assay was carried out by flow cytometry, which supported that apoptosis is the major mechanism.
- Taghavi, Faezeh,Gholizadeh, Mostafa,Saljooghi, Amir Sh.,Ramezani, Mohammad
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p. 1953 - 1964
(2017/10/27)
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- [Cu(phen)(PPh3)2]NO3-catalyzed microwave-assisted green synthesis of 5-substituted 1H-tetrazoles
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Abstract: An efficient synthetic methodology for construction of 5-substituted 1H-tetrazoles under microwave irradiation in green medium is described. With [Cu(phen)(PPh3)2]NO3 as catalyst and H2O-isopropyl alcohol (IPA) as reaction medium, various substituted nitriles underwent (3?+?2) cycloaddition reaction with NaN3 under microwave irradiation to provide corresponding 5-substituted 1H-tetrazoles in high yield. This method is not only efficient and general but also benefits from high functional group tolerance. This environmentally friendly synthetic methodology is visualized as an alternative to existing procedures, providing a simple route to privileged scaffolds.
- Padmaja,Meena,Maiti, Barnali,Chanda, Kaushik
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p. 7365 - 7374
(2017/09/06)
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- Remote meta-C–H Cyanation of Arenes Enabled by a Pyrimidine-Based Auxiliary
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An easily removable pyrimidine-based auxiliary has been employed for the remote meta-C?H cyanation of arenes. The scope of this Pd-catalyzed cyanation reaction using copper(I) cyanide as the cyanating agent was demonstrated with benzylsilanes, benzylsulfonates, benzylphophonates, phenethylsulfonates, and phenethyl ether derivatives. The method was utilized for the synthesis of pharmaceutically valuable precursors.
- Bag, Sukdev,Jayarajan, Ramasamy,Dutta, Uttam,Chowdhury, Rajdip,Mondal, Rahul,Maiti, Debabrata
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supporting information
p. 12538 - 12542
(2017/09/12)
-
- Magnetically separable Fe3O4@chitin as an eco-friendly nanocatalyst with high efficiency for green synthesis of 5-substituted-1H-tetrazoles under solvent-free conditions
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The present study describes an efficient, eco-friendly and simple method for the synthesis of 5-substituted-1H-tetrazoles catalyzed by magnetite-chitin (Fe3O4@chitin) as a green and recyclable catalyst. Fe3O4@chitin was initially prepared using hydrothermal synthesis. Subsequently, the structure, morphology, and magnetic properties of the prepared nanocatalyst were studied with some different spectroscopic, microscopic and thermogravimetric techniques such as FT-IR, XRD, SEM, TEM, VSM and TGA. Obtained results showed that Fe3O4@chitin nanoparticles exhibited uniform cubic shape and were well monodispersed. Also, magnetic measurement revealed that the synthesized nanocatalyst had superparamagnetic features. The application of this new nanocatalyst allows the synthesis of a variety of tetrazoles through the reaction of nitriles with 1-butyl-3-methylimidazolium azide ([bmim][N3]) under solvent-free conditions. This synthetic pathway is a green protocol offering significant advantages, such as excellent yield of products in short reaction times, mild reaction conditions, minimization of chemical waste, easy preparation of the catalyst and its recyclability up to six cycles without any considerable loss of efficiency.
- Zarghani, Monireh,Akhlaghinia, Batool
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p. 31850 - 31860
(2016/04/26)
-
- INHIBITORS OF α-AMINO-β-CARBOXYMUCONIC ACID SEMIALDEHYDE DECARBOXYLASE
-
The present disclosure discloses compounds capable of modulating the activity of α-amino-β-carboxymuconic acid semialdehyde decarboxylase (ACMSD), which are useful for the prevention and/or the treatment of diseases and disorders associated with defects in NAD+ biosynthesis, e.g., metabolic disorders, neurodegenerative diseases, chronic inflammatory diseases, kidney diseases, and diseases associated with ageing. The present application also discloses pharmaceutical compositions comprising said compounds and the use of such compounds as a medicament.
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Page/Page column 108
(2016/03/22)
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- A rapid metal free synthesis of 5-substituted-1H-tetrazoles using cuttlebone as a natural high effective and low cost heterogeneous catalyst
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A convenient, rapid and metal free synthesis of 5-substituted-1H-tetrazoles is described by [3 + 2] cycloaddition reaction of nitriles with sodium azide. The reaction was catalyzed by cuttlebone in DMSO at 110°C. Cycloaddition reaction of nitriles with sodium azide happened in the presence of mesoporous cuttlebone by "electrophilic activation" of nitriles through hydrogen bond formation between the cuttlebone and nitrile. Cuttlebone as a natural low cost heterogeneous catalyst with high porosity, high flexural stiffness, high compressive strength and high thermal stability affords 5-substituted-1H-tetrazoles rapidly with high efficiency.
- Ghodsinia, Sara S. E.,Akhlaghinia, Batool
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p. 49849 - 49860
(2015/06/25)
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- Expanded perlite: An inexpensive natural efficient heterogeneous catalyst for the green and highly accelerated solvent-free synthesis of 5-substituted-1H-tetrazoles using [bmim]N3 and nitriles
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A versatile, green and highly accelerated protocol for preparing 5-substituted-1H-tetrazoles is reported. In this method, 5-substituted-1H-tetrazoles are synthesized from nitriles and [bmim]N3, in the presence of the expanded perlite as an inexpensive natural efficient heterogeneous catalyst, under solvent-free condition. A wide variety of aryl nitriles underwent [3 + 2] cycloaddition to afford the desired tetrazoles in good to excellent yields, rapidly. This method has the advantages of high yields, short reaction times, simple methodology, and easy work-up. The catalyst can be recovered by simple filtration and reused delivering good yields.
- Jahanshahi, Roya,Akhlaghinia, Batool
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p. 104087 - 104094
(2015/12/24)
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- Cu(ii) immobilized on aminated epichlorohydrin activated silica (CAES): As a new, green and efficient nanocatalyst for preparation of 5-substituted-1H-tetrazoles
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Cu(ii) immobilized on aminated epichlorohydrin activated silica (CAES) is a novel and efficient heterogeneous nanocatalyst in the [3 + 2] cycloaddition reactions of various organic nitriles with sodium azide. The protocol can provide a series of 5-substituted-1H-tetrazoles under mild conditions in DMSO. Efficient transformation, mild reaction conditions, easy product isolation and the potential reusability of the catalyst are attractive features. The catalyst (CAES) was characterized by FT-IR, TGA, TEM, BET, SEM-EDS, CHN and ICP techniques.
- Razavi, Nasrin,Akhlaghinia, Batool
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p. 12372 - 12381
(2015/02/19)
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- Solvent-free 1H-tetrazole, 1,2,5,6-tetrahydronicotinonitrile and pyrazole synthesis using quinoline based ionic fluoride salts (QuFs): thermal and theoretical studies
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The role of ionic liquids as catalyst and solvent to mediate organic reactions is well documented. While imidazole and pyridine-based ionic liquids have traditionally been the ionic liquids of choice for organic synthesis, imidazole's inert nature and pyridine's toxicity are often viewed as impediments. In the present study, we have synthesized ionic liquids (QuFs), employing the non-toxic quinoline ring. The desired QuFs were readily prepared via N-alkylation and corresponding anion exchange with fluoride ions. The structures of the synthesized QuFs were confirmed with advanced spectroscopic techniques such as 1H and 13C NMR, IR and mass spectrometry. The potential of these newly synthesized QuFs as catalyst for click chemistry and other reactions was explored by carrying out synthesis of 5-(p-methylphenyl)-1H-tetrazole (7), 2-dicyanomethylene-6-methyl-4,6-bis(m-methoxyphenyl)-1,2,5,6-tetrahydronicotinonitrile (12), and 3,5-dimethyl-1-(p-methoxy)-1H-pyrazole (15). Detailed thermal analysis (DSC, TGA and DTG) was carried out to study the thermal stability of synthesized QuFs. Density functional theory (DFT) calculations and molecular dynamics simulations were also carried in order to establish a relationship between binding energies, and structural and dynamic characteristics of QuFs.
- Iqbal, Nafees,Hashim, Jamshed,Ali, Syed Abid,Al-Rashida, Mariya,Alharthy, Rima D.,Ahmad, Shakeel,Khan, Khalid Mohammed,Basha, Fatima Zahra,Moin, Syed Tarique,Hameed, Abdul
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p. 95061 - 95072
(2015/11/17)
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- Rhodium-catalyzed olefination of aryl tetrazoles via direct C-H bond activation
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Rh(III)-catalyzed direct olefination reaction via aromatic C-H bond activation is described using tetrazole as the directing group. This reaction provides a straightforward way for the synthesis of ortho-alkenyl aryl tetrazoles. Various functional groups tolerate the reaction conditions and afford the corresponding products in moderate to excellent yields.
- Wang, Liang,Wu, Wenting,Chen, Qun,He, Mingyang
-
supporting information
p. 7923 - 7926
(2015/01/09)
-
- Green synthesis of 5-substituted-1H-1,2,3,4-tetrazoles and 1-sustituted-1H-1,2,3,4-tetrazoles via [3+2] cycloaddition by reusable immobilized AlCl3on -Al2O3
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We report the effectiveness of the surface modified γ-Al2O3which is reusable, efficient, catalytic, safe and environmentally acceptable procedure for the conversion of both alkyl and aryl nitriles into the corresponding 5-substituted-1H-1,2,3,4-tetrazoles via [3+2] cycloaddition with sodium azide in excellent yields at mild reaction conditions (50 ° C). The catalyst also afforded 1-substituted-1H-1,2,3,4-tetrazoles by the reaction of amines, sodium azide and triethyl orthoformate. The catalyst could be recycled and was reused eleven runs without losing its activity.
- Nanjundaswamy, Hemmaragala Marishetty,Abrahamse, Heidi
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p. 2137 - 2150
(2015/01/09)
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- Hierarchically porous AlPO-5-based microspheres as heterogeneous catalysts for the synthesis of 5-substituted 1H-tetrazoles via [3+2] cycloaddition
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The research on the heterogeneous catalytic synthesis of tetrazoles has attracted great attention. In this paper, a tungsten atom-containing AlPO-5 microporous molecular sieve (termed as WAlPO-5) was designed and synthesized by the incorporation of tungst
- Kong, Dan,Liu, Yanyan,Zhang, Juan,Li, Hongbian,Wang, Xiangyu,Liu, Guangyu,Li, Baojun,Xu, Zheng
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p. 3078 - 3083
(2014/07/07)
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- Organocatalysis by an aprotic imidazolium zwitterion: A dramatic anion-cation cooperative effect on azide-nitrile cycloaddition
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An aprotic imidazole based zwitterionic-salt, 4-(3-methylimidazolium)butane sulfonate (MBS) has been found to be an efficient organocatalyst for the synthesis of 5-substituted 1H-tetrazoles by the cycloaddition of aryl nitriles with NaN3 under solvent-free conditions. Both the cation and the anion cooperatively affect the reaction and the C2-H of the imidazolium moiety plays a crucial role in "electrophilic activation" of the nitrile through hydrogen bond formation.
- Rahman, Matiur,Roy, Anupam,Ghosh, Monoranjan,Mitra, Shubhanjan,Majee, Adinath,Hajra, Alakananda
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p. 6116 - 6119
(2014/01/23)
-
- β-Cyclodextrin-mediated highly efficient [2+3] cycloaddition reactions for the synthesis of 5-substituted 1H-tetrazoles
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A β-cyclodextrin-promoted [2+3] cycloaddition reaction between nitriles and sodium azide in the presence of ammonium chloride in DMF at 120 °C is reported, affording various 5-substituted 1H-tetrazoles in good to excellent yields in short reaction times. The presence of β-CD renders the formation of a precipitate-like gel in the reaction media when heated. No precipitation occurs in the absence of NaN3 and NH4Cl. The precipitation responses with other salts such as LiCl and NiCl2 were weaker than with NH4Cl. In the present paper the application of supramolecular aggregates is reported for the [2+3] cycloaddition reaction. β-Cyclodextrin can be recovered and reused without any significant loss of activity.
- Patil, Dipak R.,Wagh, Yogesh B.,Ingole, Pravin G.,Singh, Kripal,Dalal, Dipak S.
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p. 3261 - 3266
(2013/10/01)
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- A novel approach for the synthesis of 5-substituted-1H-tetrazoles
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A series of 5-substituted-1H-tetrazoles (RCN4H) have been synthesized by cycloaddition reaction of different aryl and alkyl nitriles with sodium azide in DMSO using CuSO4?5H2O as catalyst. A wide variety of aryl nitriles underwent [3+2] cycloaddition to afford tetrazoles under mild reaction conditions in good to excellent yields. The catalyst used is readily available and environmentally friendly. Short reaction times, good to excellent yields, safe process and simple workup make this method an attractive and useful contribution to present organic synthesis of 5-substituted-1H- tetrazoles. ?2012 Sociedade Brasileira de Qui?mica.
- Akhlaghinia, Batool,Rezazadeh, Soodabeh
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p. 2197 - 2203
(2013/04/10)
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- Glycerol mediated synthesis of 5-substituted 1H-tetrazole under catalyst free conditions
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We have developed simple, cost effective and environmentally benign protocol for the synthesis of 5-substituted 1H-tetrazoles via [2,3] cycloaddition reaction from organic nitriles and sodium azide in glycerol under catalyst free condition. The corresponding 5-substituted 1H-tetrazoles were obtained with good to excellent yields (68-95%).
- Nandre, Kamalakar P.,Salunke, Jagdish K.,Nandre, Jitendra P.,Patil, Vijay S.,Borse, Amul U.,Bhosale, Sidhanath V.
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scheme or table
p. 161 - 164
(2012/06/18)
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- Ammonium acetate mediated synthesis of 5-substituted 1H-tetrazoles
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Synthesis of 5-substituted 1H-tetrazoles was achieved by [3+2] cycloaddition of nitriles and sodium azide in the presence of ammonium acetate. The reaction proceeds in situ formation of ammonium azide. Present protocol has advantage of good to excellent yields, short reaction times and simple isolation of products than reported methods. Iranian Chemical Society 2012.
- Patil, Dipak R.,Deshmukh, Mukesh B.,Dalal, Dipak S.
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p. 799 - 803
(2013/02/22)
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- InCl3-catalyzed [2+3] cycloaddition reaction: A rapid synthesis of 5-substituted 1H-tetrazole under microwave irradiation
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A series of 5-substituted 1H-tetrazole were efficiently prepared by InCl3 catalyzed (10 mol %) from structurally divert organic nitriles with sodium azide under the influence of microwave irradiation. The present protocol was successfully applied to the aliphatic, aryl, benzylic and heterocyclic nitriles and corresponding 5-substituted 1H-tetrazole were obtained in good to excellent yield (70-96%). This method gives remarkable advantages such as short reaction time, simple work-up procedure and economical beneficial.
- Patil, Vijay S.,Nandre, Kamalakar P.,Borse, Amulrao U.,Bhosale, Sidhanath V.
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experimental part
p. 1145 - 1152
(2012/05/31)
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- USE OF AZIDES IN SYNTHESIS
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Described herein are inventive methods for synthesis of tetrazoles. In some embodiments, the method involves the use of a flow reactor. The methods provided herein are capable at being carried out in short reaction times, with high yields, with minimal side reactions, and/or with minimal chance of explosions caused by the presence of azides.
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Page/Page column 16-26
(2012/03/11)
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- Towards non-peptide ANG II AT1 receptor antagonists based on urocanic acid: Rational design, synthesis and biological evaluation
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A series of o-, m- and p-benzyl tetrazole derivatives 11a-c has been designed, synthesized and evaluated as potential Angiotensin II AT1 receptor antagonists, based on urocanic acid. Compound 11b with tetrazole moiety at the m-position showed moderate, however, higher activity compared to the o- and p-counterpart analogues. Molecular modelling techniques were performed in order to extract their putative bioactive conformations and explore their binding modes.
- Agelis, George,Resvani, Amalia,Matsoukas, Minos-Timotheos,Tselios, Theodore,Kelaidonis, Konstantinos,Kalavrizioti, Dimitra,Vlahakos, Demetrios,Matsoukas, John
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experimental part
p. 411 - 420
(2011/10/04)
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- Aluminum(III) hydrogensulfate: An efficient solid acid catalyst for the preparation of 5-substituted 1H-tetrazoles
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An efficient method for preparation of 5-substituted 1H-tetrazoles via [2+3] cycloaddition of nitriles and sodium azide is reported using aluminum(III) hydrogensulfate as an effective solid acid. This method has the advantages of good yields, simple methodology, and easy workup. Copyright
- Sajadi, S. Mohammad,Khalaj, Mehdi,Jamkarani, Sayyed Mohammad Hosseini,Maham, Mehdi,Kashefib, Mehrdad
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scheme or table
p. 3053 - 3059
(2011/09/12)
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- Safe and efficient tetrazole synthesis in a continuous-flow microreactor
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Safer flow: The synthesis of 5-substituted tetrazoles in flow (see scheme) is safe, efficient, scalable, requires no metal promoter, and uses a near-equimolar amount of NaN3, yet nonetheless displays a broad substrate scope. The hazards associated with HN3 are essentially eliminated, shock-sensitive metal azides such as Zn(N3)2 are avoided, and residual NaN3 is quenched in-line with NaNO 2. Copyright
- Palde, Prakash B.,Jamison, Timothy F.
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supporting information; experimental part
p. 3525 - 3528
(2011/05/04)
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- A simple, advantageous synthesis of 5-substituted 1 h -tetrazoles
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An advantageous synthesis of 5-substituted 1H-tetrazoles has been developed by treatment of organic nitriles with NaN3 in the presence of iodine or the heterogeneous catalyst, silica-supported sodium hydrogen sulfate (NaHSO4SiO2). Georg Thieme Verlag Stuttgart New York.
- Das, Biswanath,Reddy, Cheruku Ravindra,Kumar, Duddukuri Nandan,Krishnaiah, Martha,Narender, Ravirala
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experimental part
p. 391 - 394
(2010/04/24)
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- One-pot synthesis of 5-substituted lH-tetrazoles from aryl bromides with potassium hexakis(cyano-κC)ferrate(4 -)(K4[Fe(CN)6]) as cyanide source
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A one-pot procedure for the synthesis of 5-substituted 1H-tetrazoles through the three-component reaction between an aryl bromide, potassium hexakis(cyano-κC)ferrate(4 - ) (K4[Fe(CN)6]) and NaN3 catalyzed by [Pd(OAc)2
- Zhu, Yizhong,Ren, Yiming,Cai, Chun
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experimental part
p. 171 - 175
(2009/05/30)
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- Synthesis of 2-chloromethyl-5-aryl-, 2-chloromethyl-5-(5-methyl-2-furyl)-, and 2-chloromethyl-5-(1,5-dimethyl-2-pyrrolyl)-1,3,4-oxadiazoles from tetrazole derivatives
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Acetylation of 5-aryltetrazoles, 5-(5-methyl-2-furyl)tetrazole, and 5-(1,5-dimethyl-2-pyrrolyl)tetrazole with chloroacetyl chloride was studied.
- Baranov,Tsypin,Malin,Laskin
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p. 773 - 775
(2007/10/03)
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- Pyrrolopyrrolone derivatives as inhibitors of neutrophil elastase
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There are described according to the invention compounds of formula (I) (relative stereochemistry indicated), wherein R1, R2, R3 and X are as defined in the specification, together with processes for preparing them, compositions containing them and their use as pharmaceuticals. Compounds of formula (I) are indicated inter alia for the treatment of chronic bronchitis.
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- Preparation of Tetrazoles from Organic Nitriles and Sodium Azide in Micellar Media
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An effective method for the preparation of 5-substituted tetrazoles from the corresponding nitriles in micellar media is described. It was demonstrated that almost quantitative yields of tetrazoles can be obtained if the amount of water-surfactant is optimized. The advantages of the methods presented over many others currently used are the simplicity, facility of isolation of tetrazole products and elimination of using relatively expensive solvents and reagents.
- Jursic, Branko S.,LeBlanc, Blaise W.
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p. 405 - 408
(2007/10/03)
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- Process for preparation of 5- substituted tetrazoles
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The invention is directed to a process for preparing a 5-substituted tetrazole, the process comprising the step of reacting a nitrile with an inorganic azide salt in an aromatic hydrocarbon solvent in the presence of an amine salt. According to the invention, a 5-substituted tetrazole can be produced in a high yield with ease and safety using inexpensive raw materials while the reaction is easily controlled to inhibit a side reaction.
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- Novel synthesis of 5-substituted tetrazoles from nitriles
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A variety of 5-substituted tetrazoles were prepared through the respective reactions of sodium azide with corresponding nitriles in an aromatic solvent in the presence of an amine salt.
- Koguro, Kiyoto,Oga, Toshikazu,Mitsui, Sunao,Orita, Ryozo
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p. 910 - 914
(2007/10/03)
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