- Practical synthesis of tetrazoles from amides and phosphorazidates in the presence of aromatic bases
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Tetrazoles were effectively synthesized from amides using diphenyl phosphorazidate or bis(p-nitrophenyl) phosphorazidate in the presence of aromatic bases. Various amides underwent the proposed cycloaddition reaction to provide the corresponding tetrazoles. Studies on the racemization of chiral substrates were also performed. Overall, the proposed synthesis method enables the preparation of 1,5-disubstituted and 1-substituted tetrazoles, and 5-substituted 1H-tetrazoles without using toxic or explosive reagents.
- Ishihara, Kotaro,Ishihara, Kazuki,Tanaka, Yota,Shioiri, Takayuki,Matsugi, Masato
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supporting information
(2022/02/02)
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- Removal of the Cd(II), Ni(II), and Pb(II) ions via their complexation with the uric acid-based adsorbent and use of the corresponding Cd-complex for the synthesis of tetrazoles
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The magnetic supported uric acid-based compound (Fe3O4@SiO2@CPTMS@UA) was prepared, characterized and used as a capable adsorbent for removal of the Cd(II), Ni(II) and Pb(II) ions from aqueous solution. The Freundlich and Langmuir adsorption isotherms have been used to evaluate the adsorption behaviors. The high correlation coefficient of the Langmuir model (R+2 > 0.99) reveals that the Langmuir model offers the better coordination with the experimental results and so the model of adsorption of Cd2+, Ni2+, and Pb2+ on the adsorbent is more compatible with the Langmuir model, and the maximum adsorption capacity for the Cd, Ni, and Pb ions are about 285.7, 45.06 and 145.09 mg/g. Then, the corresponding Cd-complex (Fe3O4@SiO2@CPTMS@ UA@Cd) was also prepared, characterized and applied as an efficient heterogeneous nano-catalyst for the synthesis of diverse tetrazoles.
- Ahmadi, Sharareh,Ariannezhad, Maryam,Habibi, Davood,Heydari, Somayyeh,Jafari, Ali
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- Oxidation/ MCR domino protocol for direct transformation of methyl benzene, alcohol, and nitro compounds to the corresponding tetrazole using a three-functional redox catalytic system bearing TEMPO/Co(III)-porphyrin/ Ni(II) complex
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A redox catalytic system for oxidation-reduction reactions and the domino preparation of tetrazole compounds from nitro and alcohol precursors was designed, prepared and characterized by UV–vis, GPC, TGA, XRD, EDX, XPS, VSM, FE-SEM, TEM, DLS, BET, NMR, and ICP analyses. The catalyst was prepared via several successive steps by demetalation of chlorophyll b, copolymerization with acrylated TEMPO monomers, complexation with Ni and Co metals (In two different steps), then immobilized on magnetic nanoparticles. The presence of three functional groups including TEMPO, coordinated cobalt, and coordinated nickel in the catalyst, allowed the oxidation of various types of alcohols, alkyl benzenes as well as the reduction of nitro compounds by a single catalyst. All reactions yielded up to 97 % selectivity for oxidation and reduction reactions. Next, the ability of the catalyst to successfully convert alcohol, methyl benzenes and nitro to their corresponding tetrazoles was studied.
- Mahmoudi, Boshra,Rostami, Amin,Kazemnejadi, Milad,Hamah-Ameen, Baram Ahmed
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- Efficient reduction of nitro compounds and domino preparation of 1-substituted-1H-1,2,3,4-tetrazoles by Pd(ii)-polysalophen coated magnetite NPs as a robust versatile nanocomposite
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A new, versatile, and green methodology has been developed for the efficient NaBH4-reduction of nitroarenes as well as the domino/reduction MCR preparation of 1-substituted-1H-1,2,3,4-tetrazoles using Pd(ii)-polysalophen coated magnetite NPs as an efficient heterogeneous magnetically recyclable nanocatalyst. Polysalophen was firstly prepared based on a triazine framework with a high degree of polymerization, then coordinated to Pd ions and, finally, the resulting hybrid was immobilized on magnetite NPs. The catalyst was characterized by various instrumental and analytical methods, including GPC, DLS, N2adsorption-desorption, TGA, VSM, TEM, HRTEM, EDX, XPS, XRD, and ICP analyses. The catalyst possesses dual-functionality including the reduction of nitroarenes and the construction of tetrazole rings all in one stepviaa domino protocol. High to excellent yields were obtained for both nitro reduction and the direct preparation of 1-substituted-1H-1,2,3,4-tetrazoles from nitro compounds. Insight into the mechanism was conducted by XPSin situas well as DLSin situalong with several control experiments. Recyclability of the catalyst was studied for 6 consecutive runs along with metal leaching measurements in each cycle.
- Xu, DaPeng,Xiong, Meilu,Kazemnejadi, Milad
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p. 12484 - 12499
(2021/04/14)
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- Polymer-Supported Fe-Phthalocyanine Derived Heterogeneous Photo-Catalyst for the Synthesis of Tetrazoles Under Visible Light Irradiation
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Abstract: Herein, a polymer supported Fe-Phthalocyanine entangled with carboxyl functionalized benzimidazolium moiety (PSFePcCFBM) explored as heterogenous photocatalyst, for regioselective synthesis of 1H-tetrazoles from sodium azide and other affordable
- Khajone, Vijay Baburao,Balinge, Kamlesh Rudreshwar,Bhagat, Pundlik Rambhau
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p. 1948 - 1960
(2020/11/23)
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- The anchoring of a Cu(ii)-salophen complex on magnetic mesoporous cellulose nanofibers: green synthesis and an investigation of its catalytic role in tetrazole reactions through a facile one-pot route
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Today, most synthetic methods are aimed at carrying out reactions under more efficient conditions and the realization of the twelve principles of green chemistry. Due to the importance and widespread applications of tetrazoles in various industries, especially in the field of pharmaceutical chemistry, and the expansion of the use of nanocatalysts in the preparation of valuable chemical reaction products, we decided to use an (Fe3O4@NFC@NSalophCu)CO2H nanocatalyst in this project. In this study, the synthesis of the nanocatalyst (Fe3O4@NFC@NSalophCu)CO2H was explained in a step-by-step manner. Confirmation of the structure was obtained based on FT-IR, EDX, FE-SEM, TEM, XRD, VSM, DLS, TGA, H-NMR, and CHNO analyses. The catalyst was applied to the synthesis of 5-substituted-1H-tetrazole and 1-substituted-1H-tetrazole derivatives through multi-component reactions (MCRs), and the performance was assessed. With advances in science and technology and increasing environmental pollution, the use of reagents and methods that are less dangerous for the environment has received much attention. Therefore, following green chemistry principles, with the help of the (Fe3O4@NFC@NSalophCu)CO2H salen complex as a nanocatalyst that is recyclable, cheap, safe, and available, the use of water as a green solvent, and reduced reaction times, the synthesis of tetrazoles can be achieved.
- Bagherzade, Ghodsieh,Ghamari kargar, Pouya
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p. 19203 - 19220
(2021/06/03)
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- One pot three component solvent free synthesis of N-substituted tetrazoles using RuO2 /MMT catalyst
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A facile, one-pot three component catalytic method is developed for the synthesis of N-substituted tetrazole using RuO2/MMT nanocomposite. It is characterized with low and wide angle XRD which suggests that RuO2 nanoparticles are evenly dispersed on the surface of MMT while FESEM images indicate a spherical morphology having size in the range of 40-50 nm. The catalytic efficiency is evaluated for three component one-pot synthesis of the tetrazole using various amine, sodium azide and triethyl-ortho-formate under solvent free condition. This strategy has resulted in good to excellent yields (84 – 97percent) of N-substituted tetrazoles within moderate reaction time. Moreover, the catalyst possesses excellent reusability up to five cycles with only 5percent decrease in the yield of tetrazole after 5th cycle. The beneficial catalytic activity of the bifunctional nanocomposite is attributed to the uniformly dispersed RuO2 nanoparticles on the surface of MMT where RuO2 site is responsible for coordination of isocyanide intermediate while strong acidic character of MMT induces condensation and cyclization steps in a synergic manner. Thus, it can be argued that RuO2/MMT nanocomposite possesses potential applications for Multi Component Reactions (MCR) in terms of efficient and sustainable manner.
- Chikate, Rajeev C.,Pawar, Hari R.
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- [3+1+1] type cyclization of ClCF2COONa for the assembly of imidazoles and tetrazolesvia in situgenerated isocyanides
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A facile synthesis of imidazoles and tetrazolesvia[3+1+1] type cyclization of ClCF2COONa is developed. A diverse array of imidazoles and tetrazoles were obtained in decent yieldsviaisocyanide intermediates. Notably, this is the first example of the cycloaddition ofin situgenerated isocyanides.
- Song, Qiuling,Wang, Ya,Zhou, Yao
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supporting information
p. 6106 - 6109
(2020/06/10)
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- Copper coordinated-poly(α-amino acid) decorated on magnetite graphene oxide as an efficient heterogeneous magnetically recoverable catalyst for the selective synthesis of 5- and 1-substituted tetrazoles from various sources: A comparative study
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In this work, poly(α-amino acid)-Cu(II) complex immobilized on magnetite graphene oxide (GO/Fe3O4?PAA-Cu-complex) was prepared via a multistep synthesis and employed as an efficient, heterogeneous, magnetically recyclable nanocatalyst for one-pot, three component synthesis of 5- and 1-substituted tetrazoles using different substrates including benzaldehydes, benzonitriles, and anilines in mild conditions. The different approaches were mechanically investigated and compared. The catalyst was fully characterized by Fourier transform infrared (FTIR), thermogravimetric analysis (TGA), X-ray diffraction (XRD), vibrating sample magnetometer (VSM), energy dispersive X-ray spectroscopy (EDX), inductively coupled plasma (ICP), FE-SEM and TEM analyses. The magnetic nanocatalyst could be readily separated from the reaction mixture by an external magnet and reused for several times without significant loss of catalytic activity. Also, the spectroscopic analysis revealed the stability and durability of the catalyst. Finally, the chemoselectivity of the method was investigated by the various combinations of aldehyde, nitrile, and oxime.
- Kazemnejadi, Milad,Mahmoudi, Boshra,Sharafi, Zeinab,Nasseri, Mohammad A.,Allahresani, Ali,Esmaeilpour, Mohsen
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- Green synthesis of the 1-substituted 1H-1, 2, 3, 4-tetrazoles over bifunctional catalyst based on copper intercalated into Mg/Al hydrotalcite modified magnetite nanoparticles
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An effective one-pot, convenient process for the synthesis of 1- substituted 1H-tetrazoles from triethyl orthoformate, amines, and sodium azide is described using copper (II) doped and immobilized on functionalized magnetic hydrotalcite (Fe3O4/HT-NH2 CuII) as a novel recyclable catalyst. The application of this catalyst allows the synthesis of a variety of tetrazoles in good to excellent yields in water. The new catalyst was characterized using Fourier transform infrared (FT-IR) spectroscopy, X-ray diffraction (XRD), scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX), thermogravimetric analysis (TGA), vibration sample magnetometry (VSM) and inductively coupled plasma analysis (ICP-OES). This new procedure offers several advantages such as short operational simplicity, practicability, and applicability to various substrates and the absence of any tedious workup or purification. The loading amount of CuII (doped and immobilized) on functionalized magnetic hydrotalcite was indicated to be 4.66 mmol g?1, obtained from the ICP-OES analysis. Also, the excellent catalytic performance, thermal stability, and separation of the catalyst make it an excellent heterogeneous system and a useful alternative to other heterogeneous catalysts. Also, the catalyst could be magnetically separated and reused six times without significant loss of catalytic activity.
- Salimi, Mehri,Zamanpour, Azadeh
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- Fe3O4?Hydrotalcite-NH2-CoII NPs: A novel and extremely effective heterogeneous magnetic nanocatalyst for synthesis of the 1-substituted 1H-1, 2, 3, 4-tetrazoles
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In this study, we present a versatile and easy procedure for modifying a ferrite nanoparticles so step by step. A new nanocatalyst was prepared via CoII immobilized onto an aminated ferrite nanoparticles (Fe3O4?HT?AEPH2-CoII). The catalyst was fully characterized by FT-IR, EDX, FE-SEM, TGA, XRD, and VSM analyses. In the preparation of 1-substituted-1-H-tetrazole, the corresponding nanocatalyst shown great catalytic activity. The reaction contains expeditious reusable catalyst (Fe3O4?AEPH2-CoII) that promotes condensation between sodium azide, triethyl ortho-formate, and diversity of heterocyclic/aromatic amines. Also, an environmentally toxic solvent was eliminated. A significant improvement in the synthetic efficacy (95%, yield) was obtained by this new sustainable and eco-friendly protocol as well as high purity. The current procedure as a green protocol offers benefits including a simple operational procedure, an excellent yield of products, mild reaction conditions, minimum chemical wastes, short reaction time, and easy catalyst synthesis. Without any significant reduction in the catalytic performance, up to four recyclability cycles of the catalyst were obtained. The optimization results suggest that the best condition in the preparation of tetrazole derivatives is 0.005 g of the Fe3O4?HT?AEPH2-CoII catalyst where H2O is the solvent at 90 °C. The proposed protocol could be applied on a wider scope of the substrate (i.e., electron-deficient and electron-rich).
- Esmaeli-nasrabadi, Farzaneh,Salimi, Mehri,Sandaroos, Reza
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- Synthesis of boron-containing tetrazoles under neutral microwave-assisted conditions
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In this report, the mild synthetic strategies for the synthesis of two series of boron-containing tetrazoles were included. For the first series, a boron-containing isocyanide reacted with TMS-N3 to afford the desire products. The reaction took
- Chen, Yu-Yun,Lin, Wan-Xin,Hsu, Kai-Wei,Li, Wan-Chi,Wang, Chih-Hsuan,Yu, Jui-Ping,Chang, Chia-Wen,Qiu, Shuo-Bei,Hsieh, Po-Shiuan,Chen, Yi-Wei,Pan, Po-Shen
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p. 5375 - 5388
(2019/11/03)
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- One-pot green synthesis of Cu/bone nanocomposite and its catalytic activity in the synthesis of 1-substituted 1H-1,2,3,4-tetrazoles and reduction of hazardous pollutants
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In this work, a simple and green method is reported for the biosynthesis of Cu/bone nanocomposite using Cordyline fruticosa extract as a stabilizer and reductant. Animal bone was used as a natural support to prevent the accumulation of Cu nanoparticles. The catalytic activity of Cu/bone nanocomposite was assessed in the synthesis of 1-substituted 1H-1,2,3,4-tetrazoles and reduction of various organic dyes, including 4-nitrophenol (4-NP), nigrosin (NS), congo red (CR) and methylene blue (MB). The best catalytic performance in the synthesis of 1-substituted tetrazoles was achieved using 0.05?g of Cu/bone nanocomposite at 120°C. In addition, under optimal conditions, the absorption bands corresponding to 4-NP, CR, NS and MB completely disappeared after about 6?min, 3?min, 50?s and 7?s, respectively. The biosynthesis protocol used in the preparation of Cu/bone nanocomposite offers a very attractive area for further research.
- Maham, Mehdi,Nasrollahzadeh, Mahmoud
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- Synthesis of Tetrazoles from Amines Mediated by New Copper Nanocatalyst
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New copper nanocatalyst was prepared by coating Fe3O4 magnetic nanoparticles with tetraethyl orthosilicate (TEOS), followed by functionalization with 3-chloropropyl(trimethoxy)silane and 4H-1,2,4-tri-azol-4-amine and complexation with copper(II) chloride. The new catalyst was characterized by various spectroscopic methods and was successfully used in the synthesis of 1-aryl-1H-tetrazoles by reaction of aromatic amines with sodium azide and triethyl orthoformate under solvent-free conditions at 100°C.
- Ariannezhad,Habibi,Heydari
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p. 1591 - 1597
(2019/12/28)
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- Synthesis of Tetrazoles Catalyzed by Novel Cobalt Magnetic Nanoparticles
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A novel magnetic Co nanoparticle catalyst was prepared by coating Fe304magnetic nanoparticles with tetraethyl orthosilicate functionalized with (3-chloropropyl)trimethoxysilane and 2-amino-5-mercapto-1,3,4-thiadiazole ligands followed by complexation with Co(OAc)4. The catalyst was then characterized and applied for the synthesis of various tetrazoles by the reactions of amines with sodium azide and triethyl orthoformate in solvent-free conditions at 100°C.
- Sarrafioun,Jamehbozorgi,Ramezani
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p. 1777 - 1784
(2020/01/11)
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- Novel two step synthesis of bis/Mono 1-aryl-1H-tetrazole-5-carboxylic acid
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Some novel compounds of bis/mono 1-aryl-1H-tetrazole-5-carboxylic acid are synthesized by the hydrolysis of two different synthesized esters, they are ethyl-1-aryl-1H-tetrazole-5-carboxylate and ethyloxo(1-aryl-1H-tetrazol-5-yl)acetate. The ethyl-1-aryl-1
- Chandrakumari, Sambandam,Sivakumar, Dhanavel,Manikandan, Haridoss,Gopalakrishnan, Mannuthusamy
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p. 1913 - 1925
(2019/05/15)
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- Docking, Synthesis, Spectral Characterization, and Evaluation of In Vitro Antifungal Activity of Bis/Monophenyl-1-aryl-1H-tetrazole-5-carboxylate
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Some novel compounds of bis/monophenyl-1-aryl-1H-tetrazole-5-carboxylate were synthesized by the equimolar reaction between bis/mono-1-aryl-1H-tetrazole and phenyl chloroformate in the presence of NaOH in dry tetrahydrofuran. The content was stirred for 4
- Sambandam, Chandrakumari,Dhanavel, Sivakumar,Haridoss, Manikandan,Mannuthusamy, Gopalakrishnan
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p. 2779 - 2786
(2019/08/26)
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- Application of the Fe3O4@1,10-phenanthroline-5,6-diol@Mn nano-catalyst for the green synthesis of tetrazoles and its biological performance
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The Fe3O4 magnetic particles were modified with 1,10-phenanthroline-5,6-diol (Phen) and the related Mn complex (Fe3O4@Phen@Mn) synthesized as a heterogeneous catalyst to be used for the one-pot three-component synthesis of various tetrazoles. The catalysts were characterized by several methods, such as the elemental analysis, FT-IR, X-ray powder diffraction, dispersive X-ray spectroscopy, scanning electron microscopy, transmission electron microscopy, dynamic light scattering, thermogravimetric-differential thermal analysis, vibrating sample magnetometer and X-ray photoelectron spectroscopy. In addition, the antioxidant and antibacterial activities of the catalyst and its Phen ligand were in vitro screened with 2,2-diphenyl-1-picrylhydrazyl by free radical scavenging methods. Results showed that the synthesized compounds possess strong antioxidant activity (IC50; 0.172 ± 0.005 mg ml?1) as well as a good antibacterial potential in comparison to standards.
- Habibi, Davood,Heydari, Somayyeh,Gil, Antonio,Afsharfarnia, Mina,Faraji, Alireza,Karamian, Roya,Asadbegy, Mostafa
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- Isocyanide based multicomponent click reactions: a green and improved synthesis of 1-substituted 1H-1,2,3,4-tetrazoles
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An improved ultrasound assisted green synthesis of 1-substituted 1H-1,2,3,4-tetrazoles via a novel isocyanide based multicomponent click reaction (IMCCR) under mild, solvent, catalyst and column-free conditions has been developed. This new, green and sust
- Pharande, Shrikant G.,Rentería-Gómez, Manuel A.,Gámez-Monta?o, Rocío
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supporting information
p. 11294 - 11298
(2018/07/25)
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- Visible-light driven regioselective synthesis of 1H-tetrazoles from aldehydes through isocyanide-based [3 + 2] cycloaddition
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A novel and green Co@g-C3N4 catalyzed visible light driven direct regioselective synthesis of 1H-tetrazoles directly from various aldehydes and sodium azide is reported. Herein, NaN3 not only behaves as a three-nitrogen do
- Verma, Fooleswar,Sahu, Anjumala,Singh, Puneet K.,Rai, Ankita,Singh, Manorama,Rai, Vijai K.
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supporting information
p. 3783 - 3789
(2018/08/21)
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- Preparation of Fe3O4@5,10-dihydropyrido[2,3-b]quinoxaline-7,8-diol copper complex: A capable nanocatalyst for the green synthesis of 1-substituted 1H-tetrazoles
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Fe3O4 magnetic nanoparticles functionalized with 5,10-dihydropyrido[2,3-b]quinoxaline-7,8-diol were synthesized as was their complex with copper as a novel nanomagnetic iron oxide catalyst via a simple and green method, and characterized using various techniques. The capability of the catalyst was evaluated in the one-pot three-component synthesis of different tetrazoles, which showed very good results. Mild reaction conditions, good reusability and simple magnetic work-up make this methodology interesting for the efficient synthesis of tetrazoles.
- Habibi, Davood,Pakravan, Narges,Arabi, Ameneh,Kaboudvand, Zahra
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- Synthetic manifestation of nitro substituted tetrazole-N-(hetero)aryl derivatives and energetic studies
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A workable cost-efficient synthetic method for the construction of nitro substituted tetrazole-N-aryl/heteroaryl derivatives is discussed here. The energetic functional groups-NO2,-NHNO2 and-N3 are reliably inserted into the molecular backbone, making the tetrazole-N-aryl derivatives highly energetic and insensitive to heat and impact. For example, the tetrazole derivatives 7 and 8, bearing a-NO2 or a-NHNO2 group, exhibit energetic properties close to RDX, but with enhanced insensitivity. Most of the synthesized compounds show exothermic decomposition and are consequently useful for energetic material applications.
- Kommu, Nagarjuna,Balaraju,Ghule, Vikas D.,Sahoo, Akhila K.
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supporting information
p. 7366 - 7371
(2017/04/26)
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- One-pot synthesis of 1- and 5-substituted 1H-tetrazoles using 1,4-dihydroxyanthraquinone–copper(II) supported on superparamagnetic Fe3O4@SiO2 magnetic porous nanospheres as a recyclable catalyst
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An effective one-pot, convenient process for the synthesis of 1- and 5-substituted 1H-tetrazoles from nitriles and amines is described using1,4-dihydroxyanthraquinone–copper(II) supported on Fe3O4@SiO2 magnetic porous nanospheres as a novel recyclable catalyst. The application of this catalyst allows the synthesis of a variety of tetrazoles in good to excellent yields. The preparation of the magnetic nanocatalyst with core–shell structure is presented by using nano-Fe3O4 as the core, tetraethoxysilane as the silica source and poly(vinyl alcohol) as the surfactant, and then Fe3O4@SiO2 was coated with 1,4-dihydroxyanthraquinone–copper(II) nanoparticles. The new catalyst was characterized using Fourier transform infrared spectroscopy, X-ray diffraction, transmission electron microscopy, field emission scanning electron microscopy, dynamic light scattering, thermogravimetric analysis, vibration sample magnetometry, X-ray photoelectron spectroscopy, nitrogen adsorption–desorption isotherm analysis and inductively coupled plasma analysis. This new procedure offers several advantages such as short reaction times, excellent yields, operational simplicity, practicability and applicability to various substrates and absence of any tedious workup or purification. In addition, the excellent catalytic performance, thermal stability and separation of the catalyst make it a good heterogeneous system and a useful alternative to other heterogeneous catalysts. Also, the catalyst could be magnetically separated and reused six times without significant loss of catalytic activity. Copyright
- Esmaeilpour, Mohsen,Javidi, Jaber,Zahmatkesh, Saeed
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p. 897 - 904
(2016/10/18)
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- 6-NITRO-2,3-DIHYDROIMIDAZO[2,1-b]OXAZOLES AND A PROCESS FOR THE PREPARATION THEREOF
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The present invention relates to newer generation of triazoles, tetrazoles, isoxazoles, urea and sulphonamide functionalities containing 6-nitro-2, 3-dihydronitroimidazooxazoles agents of formula 1, their method of preparation, and their use as drugs for
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- Cross-linked poly (4-vinylpyridine) supported azide ion as a versatile and recyclable polymeric reagent for synthesis of 1-substituted-1H-1,2,3,4- tetrazoles
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Cross-linked poly (4-vinylpyridine) supported azide ion, [P 4-VP]N3, is easily prepared and used as an efficient polymeric reagent for synthesis of 1-substituted-1H-1,2,3,4-tetrazoles via condensation reaction of azide ion, primary aromatic amines, and triethyl orthoformate in glacial acetic acid. After optimization of the reaction conditions, a wide variety of primary aromatic amines were also subjected to preparation of the corresponding 1-aryl-1 H-1,2,3,4- tetrazoles using [P 4-VP]N3 under heterogeneous conditions. In this method, the reaction times were very short and the isolated yields were excellent (90-98 %). 1-Aryl-1H-1,2,3,4- tetrazole products were characterized by Fourier transform infrared (FT-IR) and some of them were also characterized by proton nuclear magnetic resonance (1H NMR) spectroscopy, and physical properties were compared with the literature values of known compounds. The spent polymeric reagent were regenerated quantitatively and reused for several cycles without significant loss of their activity.
- Karimi Zarchi, Mohammad Ali,Nazem, Fatemeh
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- Facile synthesis of 1- and 5-substituted 1H-tetrazoles catalyzed by recyclable ligand complex of copper(II) supported on superparamagnetic Fe 3O4@SiO2 nanoparticles
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We report a new method for preparing functionalized superparamagnetic Fe3O4@SiO2 possessing high saturation magnetization. Magnetite particles were prepared by simple co-precipitation method in aqueous medium, and then Fe3O4@SiO2 nanosphere was synthesized by using nano Fe3O4 as the core, TEOS as the silica source and polyethylene glycol (PEG 1000) as the surfactant. Then, the silica-coated Fe3O4 nanoparticles were covered with ligand complex of Cu(II). The functionalized magnetic core-shell nanoparticles (MNPs) were investigated by Fourier transform infrared spectroscopy, transmission electron microscopy, scanning electron microscopy, X-ray diffraction, thermogravimetric analysis, dynamic light scattering and N2 adsorption/desorption. Also, its Cu content was determined by inductively coupled plasma (ICP) analyzer. Then, the immobilized copper complex was used as an efficient catalyst for synthesis of 1- and 5-substituted 1H-tetrazoles from nitriles and amines in good to excellent yields. The results show that the supported catalyst could be conveniently recovered through the use of an external magnetic field and reused for subsequent reactions for at least 6 times with less deterioration in catalytic activity.
- Esmaeilpour, Mohsen,Javidi, Jaber,Nowroozi Dodeji, Fatemeh,Mokhtari Abarghoui, Mehdi
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- HClO4-SiO2 as an efficient and reusable heterogeneous catalyst for the synthesis of 1-substituted tetrazoles
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An efficient and direct protocol is described for the preparation of 1-substituted 1H-1,2,3,4-tetrazoles by the reaction of primary amines, triethyl orthoformate and sodium azide in the presence of catalytic amount of silica-supported perchloric acid under solvent-free and heterogeneous conditions. The thermal solvent-free green procedure offers advantages such as simple methodology, easy work-up, high yield, recovery and reusability of catalyst.
- Bahari, Siavash,Rezaei, Akbar
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- Salen complex of Cu(II) supported on superparamagnetic Fe3O 4@SiO2 nanoparticles: An efficient and recyclable catalyst for synthesis of 1- and 5-substituted 1H-tetrazoles
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An efficient and general method has been developed for synthesis of 1- and 5-substituted 1H-tetrazoles from nitriles and amines using magnetite nanoparticles immobilized Salen Cu(II) as an efficient and recyclable catalyst. The structural and magnetic properties of functionalized magnetic silica are identified by transmission electron microscopy (TEM), scanning electron microscopy (SEM) and vibrating sample magnetometer (VSM) instruments. NMR, FT-IR, elemental analysis and XRD were also used for identification of these structures. Nanocatalyst can be easily recovered by a magnetic field and reused for subsequent reactions for at least 7 times with less deterioration in catalytic activity.
- Dehghani, Farzaneh,Sardarian, Ali Reza,Esmaeilpour, Mohsen
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- Highly efficient synthesis of 1- and 5-substituted 1H-tetrazoles using chitosan derived magnetic ionic liquid as a recyclable biopolymer-supported catalyst
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A general method for the efficient synthesis of 1- and 5-substituted 1H-tetrazoles from nitriles and amines is described using chitosan supported magnetic ionic liquid nanoparticles (CSMIL) as a novel heterogeneous catalyst. The application of this catalyst allows the synthesis of a variety of tetrazoles in high yields at low temperature. This new magnetic catalyst has been prepared from chitosan (the most abundant biopolymer in nature and cheap industrial waste) and methyl imidazole (a widely available backbone of ionic liquids) which was reacted with FeCl3 to obtain the CS-EMImFeCl4 catalyst. This methodology illustrates a very simple procedure, with wide applicability, environmental friendliness and reusability of catalyst. The new catalyst was characterized using some different microscopic and spectroscopic techniques such as transmission electron microscopy (TEM), scanning electron microscopy (SEM), FTIR spectroscopy, and Raman spectroscopy. The novel catalyst has therefore a great potential to be used in green processes. The Royal Society of Chemistry 2013.
- Khalafi-Nezhad, Ali,Mohammadi, Somayeh
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p. 4362 - 4371
(2013/05/08)
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- Synthesis of 1-substituted tetrazoles using CoFe2O4 nanoparticles as a magnetically recoverable and reusable catalyst
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Nano CoFe2O4 is found to be efficient catalyst for synthesis of 1-substituted 1H-1,2,3,4-tetrazoles under solvent- free conditions. The significant advantages of this methodology are high yields, elimination of dangerous and harmful hydrazoic acid and simple work-up procedure. The catalyst was easily isolated from the reaction mixture by magnetic decantation using an external magnet and reused with no significant loss in its reactivity.
- Bahari, Siavash
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p. 527 - 531
(2013/08/23)
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- A stereocontrolled 1,2-addition reaction of tetrazoles with alkyl propiolates for the synthesis of highly functionalized enamines
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A stereocontrolled 1,2-addition reaction of 1-aryl-1H-tetrazoles with alkyl propiolates for the synthesis of highly functionalized enamines was developed. In the presence of silver oxide (Ag2O), the 1,2-addition reaction generated (Z)-N-cyano enamines in good yields with exclusive formation of the Z-isomers. Meanwhile, the 1,2-addition reaction generated (E)-N-cyano enamines in the presence of Ag2O and potassium carbonate (K2CO 3) with high stereoselectivity and yields. Copyright
- Luo, Kai,Meng, Lingguo,Zhang, Yicheng,Zhang, Xiuli,Wang, Lei
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p. 765 - 780
(2013/04/10)
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- Synthesis and evaluation of 1,5-disubstituted tetrazoles as rigid analogues of combretastatin A-4 with potent antiproliferative and antitumor activity
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Tubulin, the major structural component of microtubules, is a target for the development of anticancer agents. Two series of 1,5-diaryl substituted 1,2,3,4-tetrazoles were concisely synthesized, using a palladium-catalyzed cross-coupling reaction, and identified as potent antiproliferative agents and novel tubulin polymerization inhibitors that act at the colchicine site. SAR analysis indicated that compounds with a 4-ethoxyphenyl group at the N-1 or C-5 position of the 1,2,3,4-tetrazole ring exhibited maximal activity. Several of these compounds also had potent activity in inhibiting the growth of multidrug resistant cells overexpressing P-glycoprotein. Active compounds induced apoptosis through the mitochondrial pathway with activation of caspase-9 and caspase-3. Furthermore, compound 4l significantly reduced in vivo the growth of the HT-29 xenograft in a nude mouse model, suggesting that 4l is a promising new antimitotic agent with clinical potential.
- Romagnoli, Romeo,Baraldi, Pier Giovanni,Salvador, Maria Kimatrai,Preti, Delia,Aghazadeh Tabrizi, Mojgan,Brancale, Andrea,Fu, Xian-Hua,Li, Jun,Zhang, Su-Zhan,Hamel, Ernest,Bortolozzi, Roberta,Basso, Giuseppe,Viola, Giampietro
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experimental part
p. 475 - 488
(2012/02/16)
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- Efficient uncatalyzed conversion of primary and secondary thioamides into 1-substituted, 5-substituted, 1, 5-disubstituted and annulated tetrazoles
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Unprecedented high-yield simple and mild conversion of primary aliphatic and aromatic thioamides into 5-substituted tetrazoles on treatment with a combination of tetrachlorosilane and sodium azide in refluxing acetonitrile has been achieved. Secondary acyclic, cyclic, and heterocyclic thioamides could also be transformed in high yields into 1-substituted, 1,5-disubstituted, or annulated tetrazoles under the same reaction condition. Copyright Taylor & Francis Group, LLC.
- El-Ahl, Abdel-Aziz S.,Amer, Fatty A.,Elbeheery, Akram H.
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experimental part
p. 2226 - 2235
(2012/03/26)
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- Building heterocyclic systems with RC(OR)2+ carbocations in recyclable bronsted acidic ionic liquids: Facile synthesis of 1-substituted 1H-1,2,3,4-tetrazoles, benzazoles and other ring systems with CH(OEt)3 and EtC(OEt)3 in [EtNH 3][NO3] and [PMIM(SO3H)][OTf]
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1-Aryl/alkyl-1H-1,2,3,4-tetrazoles can conveniently be synthesized in one-pot reactions from the corresponding amines by reaction with TMSN 3 and CH(OEt)3 using the readily available, recyclable, Bronsted acidic ionic liquids [EtNH3][NO3] IL-1 and [PMIM(SO3H)][OTf] IL-2 under mild conditions in high yields. Based on comparative reactions, whereas both ILs are excellent promoters, reactions are completed with shorter reaction times and in higher yields with IL-2. Among 24 examples provided, identical products were obtained via the two ILs, except in the case of 2-aminobenzoic acid where tetrazole was formed with IL-2 and 2-ethylquinazolin-4(3H)-one was formed with IL-1. By leaving out TMS-N 3 from the reaction, the in-situ formed CH(OEt)2 + and EtC(OEt)2+ (via their corresponding orthoesters) react under sonication with o-phenylenediamine bearing various substituents, o-aminothiophenol and o-aminophenol to form a wide array of benzazoles (benzimidazole, benzothiazole and benzoxazole) and quinazolin-4(3H)-one in high yields (18 examples). The two ILs reacted differently in reaction with 2-aminobenzamide, whereas quinazolin-4(3H)one was formed with IL-2/CH(OEt)3, the "unexpected" N-ethylquinazolin-4(3H)one was isolated with IL-1/CH(OEt)3. The latter was also formed from 2-aminobenzoic acid in IL-1/CH(OEt)3. Mechanistic implications are addressed. The reported protocols enable rapid assembly of a host of heterocyclic systems in high yields with the added advantage of recycling and re-use of the ILs.
- Aridoss, Gopalakrishnan,Laali, Kenneth K.
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experimental part
p. 2827 - 2835
(2011/06/23)
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- Green synthesis of the 1-substituted 1H-1,2,3,4-tetrazoles by application of the Natrolite zeolite as a new and reusable heterogeneous catalyst
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An efficient method for the preparation of 1-substituted 1H-1,2,3,4-tetrazoles is reported using Natrolite zeolite as a natural and heterogeneous catalyst under solvent-free conditions. This method has the advantages of high yields, simple methodology and easy work-up. The catalyst can be recovered by simple filtration and reused in good yields.
- Habibi, Davood,Nasrollahzadeh, Mahmoud,Kamali, Taghi A.
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supporting information; experimental part
p. 3499 - 3504
(2012/01/06)
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- A novel synthesis of 1-aryl tetrazoles promoted by employing the synergy of the combined use of DMSO and an ionic liquid as the solvent system at ambient temperature
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The synergy of the combined use of DMSO and an ionic liquid viz. (bbim)+Br- has brought about a mild, convenient, efficient, and rapid protocol for the synthesis of 1-substituted-1H-1,2,3,4-tetrazoles via the condensation of amines, triethyl orthoformate, and sodium azide at ambient temperature in excellent isolated yields (85-90%). The inherent Bronsted acidity of ionic liquid and high polarity of both IL and DMSO resulted in a significant enhancement in the reaction rate.
- Dighe, Satish N.,Jain, Kishor S.,Srinivasan, Kumar V.
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experimental part
p. 6139 - 6142
(2010/02/27)
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- Efficient and rapid synthesis of 1-substituted-1H-1,2,3,4-tetrazoles in the acidic ionic liquid 1-n-butylimidazolium tetrafluoroborate
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An efficient synthesis leading directly to 1-substituted-1H-1,2,3,4-tetrazoles from easily available amines and sodium azide in stoichiometric proportions using a room-temperature ionic liquid, namely, 1-n-butylimidazolium tetrafluoroborate in excellent yields is described. The inherent Br?nsted acidity and high polarity of the IL results in a significant enhancement in the reaction rate.
- Potewar, Taterao M.,Siddiqui, Shafi A.,Lahoti, Rajgopal J.,Srinivasan, Kumar V.
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p. 1721 - 1724
(2008/02/05)
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- Synthesis of 1-substituted tetrazoles via the acid-catalyzed [3+2] cycloaddition between isocyanides and trimethylsilyl azide
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1-Substituted tetrazoles were synthesized via the [3+2] cycloaddition between isocyanides and trimethylsilyl azide in the presence of an acid catalyst and MeOH. Various 1-substituted tetrazoles were obtained in good to high yields. The reaction probably p
- Jin, Tienan,Kamijo, Shin,Yamamoto, Yoshinori
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p. 9435 - 9437
(2007/10/03)
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