39889-77-5Relevant academic research and scientific papers
Functionalization of chitosan by grafting Cu(II)-5-amino-1H-tetrazole complex as a magnetically recyclable catalyst for C-N coupling reaction
Motahharifar, Narjes,Naserimanesh, Alireza,Nasrollahzadeh, Mahmoud,Sajjadi, Mohaddeseh,Shokouhimehr, Mohammadreza
, (2021/12/27)
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.
Cu(II)-N-benzyl-amino-1H-tetrazole complex immobilized on magnetic chitosan as a highly effective nanocatalyst for C-N coupling reactions
Ghafuri, Hossein,Nasrollahzadeh, Mahmoud,Sajjadi, Mohaddeseh
, (2021/07/24)
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.
Iron-promoted sulfur sequestration for the substituent-dependent regioselective synthesis of tetrazoles and guanidines
Pendem, Venkata Bhavanarushi,Tamminana, Ramana,Nannapaneni, Madhavi
, p. 499 - 509 (2021/04/09)
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.
Eco-efficient one-pot tandem synthesis of 1-aryl-1H-tetrazol-5-amine by CAN via in situ generated 1-phenylthiourea and heterocumulene
Kondhare, Dasharath D.,Bhadke, Venkat V.,Deshmukh, Sushma S.,Wakhradkar, Mahesh G.,Totawar, Balaji B.
, (2021/07/28)
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.
Chitosan supported 1-phenyl-1H-tetrazole-5-thiol ionic liquid copper(II) complex as an efficient catalyst for the synthesis of arylaminotetrazoles
Nasrollahzadeh, Mahmoud,Motahharifar, Narjes,Nezafat, Zahra,Shokouhimehr, Mohammadreza
, (2021/09/13)
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
Magnetic chitosan-copper nanocomposite: A plant assembled catalyst for the synthesis of amino- and N-sulfonyl tetrazoles in eco-friendly media
Motahharifar, Narjes,Nasrollahzadeh, Mahmoud,Taheri-Kafrani, Asghar,Varma, Rajender S.,Shokouhimehr, Mohammadreza
, (2020/01/08)
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
Ultrasound irradiation and green synthesized CuO-NiO-ZnO mixed metal oxide: An efficient sono/nano-catalytic system toward a regioselective synthesis of 1-aryl-5-amino-1H-tetrazoles
Atarod, Monireh,Safari, Javad,Tebyanian, Hamid
, p. 1993 - 2006 (2020/06/08)
An efficient approach has been reported that 1-aryl-5-amino-1H-tetrazoles are prepared from structurally diverse N-arylcyanamides and sodium azide using sono/nano-catalytic system. The mixed metal oxide nanoparticles (NPs) (CuO, NiO, and ZnO NPs) were prepared with utilizing aqueous leaves extracts of the Rheum ribes. In this study, the effect of the reaction condition was investigated on the catalytic activity and selectivity of mixed metal oxide NPs for the synthesis of aminotetrazole derivatives. In this regard, various reaction conditions were precisely compared such as reflux and ultrasonication (US). In this study, the regioselective synthesis of 1-aryl-5-amino-1H-tetrazoles with high yield was achieved by the synergistic effect between US irradiation and prepared nanocatalyst which showed the potential of sono/nano-catalytic system in organic synthesis. Furthermore, the as-prepared nanocatalyst could be reused and recovered from the reaction mixture for several times without consequential abate in its catalytic activity and selectivity.
Selective Gold-Catalysed Synthesis of Cyanamides and 1-Substituted 1H-Tetrazol-5-Amines from Isocyanides
?koch, Karel,Císa?ová, Ivana,?těpni?ka, Petr
supporting information, p. 13788 - 13791 (2018/09/14)
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.
Cobalt-promoted one-pot reaction of isothiocyanates toward the synthesis of aryl/alkylcyanamides and substituted tetrazoles
Seelam, Mohan,Kammela, Prasada Rao,Shaikh, Bajivali,Tamminana, Ramana,Bogiri, Sujatha
, p. 535 - 544 (2018/07/05)
[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.
Temperature dependent regioselective synthesis of aryl tetrazole amines using copper source
Murthy Boddapati,Emmanuel Kola,Kesana, Surendra Babu,Bollikolla, Hari Babu
, p. 177 - 183 (2018/05/09)
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
