- Nano indium oxide as a recyclable catalyst for the synthesis of arylaminotetrazoles
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Nano indium oxide is an effective heterogeneous catalyst for the reaction between aryl cyanamides and sodium azide to synthesize the arylaminotetrazoles in good yields. This method has advantages of high yields, simple methodology, short reaction times an
- Bahari, Siavash,Sabegh, Mehdi Ahmadi
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- Cobalt-promoted regioselective preparation of aryl tetrazole amines
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Abstract: A highly general, efficient and simple methodology for the regioselective synthesis of aryl tetrazole amines has been explored. The present method involves consecutive desulphurization and C- N cross-coupling reaction. Cheap, readily available and air stable cobalt catalyst has been used for this methodology. In addition, the substrate scope has been demonstrated. Graphical Abstract: A highly general, efficient and simple methodology for the regioselective synthesis of aryl tetrazole amines has been explored. The present method involves consecutive desulphurization and C- N cross-coupling reaction.
- Lakshmi, Kondraganti,Babu, Manabolu Surendra,Ramachandran, Dittakavi
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- Green chemistry: ZrOCl2·8H2O catalyzed regioselective synthesis of 5-amino-1-aryl-1H-tetrazoles from secondary arylcyanamides in water
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A green and efficient method for the synthesis of 5-amino-1-aryl-1H- tetrazoles with excellent yields and high purity from secondary arylcyanamides is described. This method is completely green because no organic solvents or protic acid catalyst is used t
- Khalili, Behzad,Darabi, Faramarz Sadeghzadeh,Eftekhari-Sis, Bagher,Rimaz, Mehdi
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- Cu(II)-N-benzyl-amino-1H-tetrazole complex immobilized on magnetic chitosan as a highly effective nanocatalyst for C-N coupling reactions
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Herein, the synthesis of a novel catalytic nanosystem with high activity and easy recoverability through immobilization of Cu(II)-N-benzyl-amino-1H-tetrazole complex on magnetic chitosan (MCS-BAT-Cu(II)) is reported. The catalytic potential of MCS-BAT-Cu(II) catalyst has been assessed in C-N coupling reaction of 5-amino-1H-tetrazole with aryl halides. Various aryl iodides/bromides were successfully coupled using MCS-BAT-Cu(II) catalyst for the synthesis of 1-aryl-5-amino-1H-tetrazoles with excellent reaction yields. In addition, the magnetic catalyst was easily and effectively separated from the reaction mixture using an external magnet and reused five times without notable loss of catalytic activity.
- Ghafuri, Hossein,Nasrollahzadeh, Mahmoud,Sajjadi, Mohaddeseh
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- Efficient synthesis of arylaminotetrazoles in water
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Arylaminotetrazole derivatives are synthesized efficiently by the reaction of arylcyanamides and sodium azide in the presence of ZnCl2 under aqueous conditions at reflux. Generally, isomer of 5-arylamino-1H-tetrazole can be obtained from arylcy
- Habibi, Davood,Nasrollahzadeh, Mahmoud,Faraji, Ali Reza,Bayat, Yadollah
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- Zno as an effective and reusable heterogeneous catalyst for the synthesis of arylaminotetrazoles
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ZnO is an effective heterogeneous catalyst for the reaction between arylcyanamides with sodium azide to synthesize the arylaminotetrazoles in good yields. This method has advantages of good yields, simple methodology, short reaction times, and easy workup
- Habibi, Davood,Nasrollahzadeh, Mahmoud
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- Application of supported Mn(iii), Fe(iii) and Co(ii) as heterogeneous, selective and highly reusable nano catalysts for synthesis of arylaminotetrazoles, and DFT studies of the products
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M@Si/Al (where M = Mn(iii), Co(ii) and Fe(iii) supported on nanosized SiO2/Al2O3) is applied as an efficient, highly reusable and heterogeneous catalyst for the regiospecific synthesis of 1-aryl-5-amino-1H-tetrazole in dim
- Habibi, Davood,Faraji, Ali Reza,Sheikh, Davood,Sheikhi, Masoome,Abedi, Samaneh
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- Functionalization of chitosan by grafting Cu(II)-5-amino-1H-tetrazole complex as a magnetically recyclable catalyst for C-N coupling reaction
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The functionalization of chitosan (as a linear polysaccharide) with a copper complex to expand the areas of its potential applications is an important scientific task. The present work reports the application of Cu(II)-5-amino-1H-tetrazole complex immobilized on modified magnetic chitosan as an effective catalyst (Fe3O4@Chitosan-Tet-Cu(II)) for C-N bond cross-coupling reaction between 5-aminotetrazole and aryl halides under ligand-free conditions in dioxane solvent. The prepared magnetic nanocatalyst was characterized by FT-IR, EDS, TEM, HRTEM, VSM, FFT, XRD, TG-DTG, ICP-MS, and elemental mapping analyses. 1-Aryl-5-amino-1H-tetrazoles were produced in high yields. The advantages of this catalytic process include simple methodology, avoiding the use of harmful catalysts, short reaction times, excellent yields, easy work-up, and environmentally friendly conditions. Fe3O4@Chitosan-Tet-Cu(II) catalyst exhibited high efficacy and reusability/recyclability even after seven consecutive cycles with low loss of catalytic activity.
- Motahharifar, Narjes,Naserimanesh, Alireza,Nasrollahzadeh, Mahmoud,Sajjadi, Mohaddeseh,Shokouhimehr, Mohammadreza
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- Chitosan supported 1-phenyl-1H-tetrazole-5-thiol ionic liquid copper(II) complex as an efficient catalyst for the synthesis of arylaminotetrazoles
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A recyclable functional hybrid catalyst was prepared via a simple method using chitosan as a linear polysaccharide and an ionic liquid. In this work, the synthesis of chitosan supported 1-phenyl-1H-tetrazole-5-thiol ionic liquid copper(II) complex (CS@Tet
- Nasrollahzadeh, Mahmoud,Motahharifar, Narjes,Nezafat, Zahra,Shokouhimehr, Mohammadreza
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- Iron-promoted sulfur sequestration for the substituent-dependent regioselective synthesis of tetrazoles and guanidines
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We have established a facile and versatile synthetic methodology for the construction of tetrazoles and guanidines in the presence of an eco-friendly, inexpensive, easily available iron reagent. Aromatic thioureas with electron-donating substituents produced their respective target products in quantitative yield. In contrast, when electron-withdrawing substituted aromatic thioureas were used, the expected products were obtained in reduced yield. However, the desired products were obtained in good yield at moderate temperature. In addition, mechanistic studies revealed that the synthetic route involved iron-based subsequent reactions of addition and removal of sulfur.
- Pendem, Venkata Bhavanarushi,Tamminana, Ramana,Nannapaneni, Madhavi
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p. 499 - 509
(2021/04/09)
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- Eco-efficient one-pot tandem synthesis of 1-aryl-1H-tetrazol-5-amine by CAN via in situ generated 1-phenylthiourea and heterocumulene
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A simple, cost-effective, environmentally benign, and efficient one-pot tandem approach to the synthesis of pharmaceutically important 1-aryl-1H-tetrazole-5-amines 3a-k and 4a-k has been described. The reaction utilized 1-phenyl thiourea, which was generated in situ from aqueous ammonia and isocyanates 1a-k, for the formation of heterocumenes using sodium azide, triethylamine, and ceric ammonium nitrate (CAN) to obtain various aryl-substituted 1H-tetrazole-5-amines (3a-k) in good to excellent yields.
- Kondhare, Dasharath D.,Bhadke, Venkat V.,Deshmukh, Sushma S.,Wakhradkar, Mahesh G.,Totawar, Balaji B.
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- Magnetic chitosan-copper nanocomposite: A plant assembled catalyst for the synthesis of amino- and N-sulfonyl tetrazoles in eco-friendly media
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A greener, cost efficient and simple method is described to prepare copper nanoparticles (NPs) immobilized on the magnetic chitosan (one of the more versatile polysaccharides) using Euphorbia falcata leaf extract as reducing/stabilizing agent. The prepare
- Motahharifar, Narjes,Nasrollahzadeh, Mahmoud,Taheri-Kafrani, Asghar,Varma, Rajender S.,Shokouhimehr, Mohammadreza
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- Selective Gold-Catalysed Synthesis of Cyanamides and 1-Substituted 1H-Tetrazol-5-Amines from Isocyanides
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The newly discovered gold-catalysed reaction of isocyanides with hydrazoic acid generated in situ from trimethylsilyl azide and methanol (or, alternatively, from NaN3/AcOH) produces either cyanamides or 1-substituted 1H-tetrazol-5-amines, depending on the amount of available HN3. The reaction proceeds selectively and in generally high yields of either product, thus providing a particularly convenient access to a wide range of substituted 1H-tetrazol-5-amines that are rather difficult to access otherwise.
- ?koch, Karel,Císa?ová, Ivana,?těpni?ka, Petr
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supporting information
p. 13788 - 13791
(2018/09/14)
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- Cobalt-promoted one-pot reaction of isothiocyanates toward the synthesis of aryl/alkylcyanamides and substituted tetrazoles
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[Figure not available: see fulltext.] The synthesis of cyanamides and tetrazoles from isothiocyanates through tandem reaction using cobalt catalyst has been demonstrated. In the case of tetrazole preparation, the reaction involved addition/desulfurization/nucleophilic addition/electrocyclization, whereas aromatic cyanamides were constructed from isothiocyanates through addition/desulfurization. Cheap cobalt sulfate was used for the synthesis of various cyanamides and tetrazoles. In addition, cobalt catalyst was found to be desulfurization reagent that has not been previously reported. The final products have been obtained from starting precursors in good to high yield.
- Seelam, Mohan,Kammela, Prasada Rao,Shaikh, Bajivali,Tamminana, Ramana,Bogiri, Sujatha
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p. 535 - 544
(2018/07/05)
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- Temperature dependent regioselective synthesis of aryl tetrazole amines using copper source
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One pot highly efficient and simple protocol for the construction of aryl tetrazole amines via desulphurization/substitution/electro cyclization/C-N cross coupling reactions from thiourea with the use of cheap, readily available and air stable copper sour
- Murthy Boddapati,Emmanuel Kola,Kesana, Surendra Babu,Bollikolla, Hari Babu
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p. 177 - 183
(2018/05/09)
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- A versatile synthesis of arylaminotetrazoles by a magnetic Fe@Phendiol@Mn nano-particle catalyst and its theoretical studies
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The Fe3O4 magnetic nano-particles were modified with 1,10-phenanthroline-5,6-diol and the relevant Mn complex (Fe@Phendiol@Mn) synthesized as a nano-magnetic heterogeneous catalyst to be used for the synthesis of various arylaminotet
- Habibi, Davood,Heydari, Somayyeh,Afsharfarnia, Mina,Rostami, Zahra
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- CoFe2O4 nanoparticles as a magnetically recoverable and reusable catalyst for the synthesis of arylaminotetrazoles and 5-aryloxytetrazoles
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An efficient and direct method is described for the synthesis of 5-arylamino-1H-tetrazoles (Isomer A) or 1-aryl-5-amino-1Htetrazoles (Isomer B) and 5-aryloxytetrazoles from arylcyanamides or cynates with nano CoFe 2O4 as a reusable a
- Bahari, Siavash,Rezaei, Akbar
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- Synthesis of thiotetrazoles and arylaminotetrazoles using rutile TiO 2 nanoparticles as a heterogeneous and reusable catalyst
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A novel method is described to prepare rutile TiO2 nanoparticles which are reusable and efficient heterogeneous catalysts for the synthesis of thiotetrazoles and arylaminotetrazoles - compounds widely used in medicinal and coordination chemistry. This procedure has the advantages of good to excellent yields of products, elimination of homogeneous catalysts and toxic and explosive reagents, simple methodology, easy work up and the reusability of the heterogeneous catalyst.
- Maham, Mehdi,Khalaj, Mehdi
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p. 502 - 506
(2014/11/08)
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- Ultrasound-promoted regioselective synthesis of 1-aryl-5-amino-1H- tetrazoles
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A new method for the regioselective synthesis of 1-aryl-5-amino-1H- tetrazoles has been developed by the reaction of arylcyanamides with sodium azide using ZnClunder ultrasound irradiation in excellent yields. Copyright
- Habibi, Davood,Nasrollahzadeh, Mahmoud,Sahebekhtiari, Hesam,Sajadi, S.Mohammad
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p. 2795 - 2798
(2013/02/21)
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- Synthesis of arylaminotetrazoles by ZnCl2/AlCl 3/silica as an efficient heterogeneous catalyst
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Arylaminotetrazoles were efficiently synthesized from secondary arylcyanamides by application of ZnCl2/AlCl3/silica as a reusable heterogeneous Lewis acid catalyst. 5-Arylamino-1H-tetrazoles can be obtained from arylcyanamides carryi
- Habibi, Davood,Nasrollahzadeh, Mahmoud
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experimental part
p. 925 - 930
(2012/08/07)
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- AlCl3 as an effective lewis acid for the synthesis of arylaminotetrazoles
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An efficient method for preparation of the arylaminotetrazoles derivatives is reported using aluminium chloride as an effective Lewis acid. Generally, 5-arylamino-1- H-tetrazole isomer can be obtained from arylcyanamides carrying electron-withdrawing subs
- Habibi, Davood,Nasrollahzadeh, Mahmoud,Bayat, Yadollah
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experimental part
p. 2135 - 2145
(2011/07/30)
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- Solvent-free preparation of arylaminotetrazole derivatives using aluminum(III) hydrogensulfate as an effective catalyst
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An efficient and simple method for the preparation of 5-arylamino-1H- tetrazole and 1-aryl-5-amino-1H-tetrazole derivatives is reported using aluminum(III) hydrogensulfate (Al(HSO4)3) as an effective heterogeneous catalyst from secon
- Khamooshi, Ferydoon,Modarresi-Alam, Ali Reza
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experimental part
p. 892 - 896
(2011/11/13)
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- A general synthetic method for the formation of arylaminotetrazoles using natural natrolite zeolite as a new and reusable heterogeneous catalyst
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An efficient method for preparation of arylaminotetrazoles is reported using natrolite zeolite as a natural catalyst. Generally, isomer of 5-arylamino-1H-tetrazole can be obtained from arylcyanamides carrying electron-withdrawing substituent on aryl ring
- Nasrollahzadeh, Mahmoud,Habibi, Davood,Shahkarami, Zahra,Bayat, Yadollah
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experimental part
p. 10715 - 10719
(2010/01/16)
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- One-pot syntheses of 5-amino-1-aryltetrazole derivatives
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A novel facile route for the introduction of 5-amino and 5-alkylamino substituents into 1-aryltetrazoles has been developed. A range of 5-amino-1-aryltetrazoles was obtained directly from the corresponding 1-aryltetrazoles in one pot by consecutive ring-opening, azidation and intramolecular cyclization. 5-Alkylamino-1-aryltetrazoles were formed by a similar mechanism from 1,4-disubstituted tetrazolium salts. An influence of the nature of aryl substituents and reaction conditions on the regioselectivity of the intramolecular cyclization of intermediate guanyl azides is revealed. Georg Thieme Verlag Stuttgart.
- Vorobiov, Andrey N.,Gaponik, Pavel N.,Petrov, Petr T.,Ivashkevich, Oleg A.
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p. 1307 - 1312
(2007/10/03)
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- On the Physicochemical Characterization of 5-Amino-1-aryl-1H-tetrazoles: Electronic Molecule Parameters from the Thermal Isomerization into 5-Arylamino-1H-tetrazoles
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The known thermal isomerization of 5-amino-1-aryl-1H-tetrazoles (A) into corresponding 5-arylamino-1H-tetrazoles (HB) was used to derive physicochemical parameters characterizing the electronic substituent effect on isomerism and dissociation equilibria. For a series of 26 tetrazoles A as starting materials the equilibrium constants (pKi) of isomerization in boiling ethylene glycol at 197°C and the dissociation constants (pKa) of the NH-acidic tetrazoles HB were determined by potentiometric titration of rapidly cooled equilibrium mixtures in water and ethanol/water with KOH at 25°C. The pK values are closely correlated with Hammett's electronic substituent constants σ and can be used as electronic molecule parameters in QSAR or QSPR (QSAR = quantitative structure-activity relationship; QSPR = quantitative structure-property relationship) studies.
- Schelenz, Thomas,Schaefer, Wieland
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p. 197 - 200
(2007/10/03)
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- The Synthesis of Aminoiminoethanenitriles, 5-Aminotetrazoles, N-Cyanoguanidines, and N-Hydroxyguanidines from Aminoiminomethanesulfonic Acids
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Examples of the reactions of aminoiminomethanesulfonic acids with cyanide, azide, cyanamide and hydroxylamine as nucleophiles are reported.
- Miller, Audrey E.,Feeney, Daniel J.,Ma, Yan,Zarcone, Lyn,Aziz, M. A.,Magnuson, E.
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p. 217 - 226
(2007/10/02)
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