Amberlyst-15 catalyzed synthesis of 5-substituted 1-H-tetrazole via [3+2] cycloaddition of nitriles and sodium azide

Shelkar, Radheshyam S.; Singh, Abhilash S.; Nagarkar, Jayashree M.

doi:10.1016/j.tetlet.2012.10.116

Cited by 72 publications

(24 citation statements)

References 24 publications

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“…It can be easily handled and removed from the reaction mixtures by simple filtration. The recovered Amberlyst‐15 can be reused several times without significant loss of activity …”

Section: Introductionmentioning

confidence: 99%

Amberlyst‐15 as a Green and Efficient Reusable Catalyst for Friedel‐Crafts Alkylation of Activated Arenes with N‐Sulfonyl Aldimines and Synthesis of Bis‐triarylmethanes

Thirupathi¹,

Venkatagiri

Reddy

2018

ChemistrySelect

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Amberlyst‐15 has been found to be an efficient and an inexpensive acidic heterogeneous catalyst for Friedel–Crafts alkylation of an activated arenes and N‐sulfonyl aldimines at room temperature. A Friedel‐Crafts alkylation products further undergoes alkylation with another mole of activated arenes to afford bis‐triarylmethanes in single transformation. Non‐toxicity and high stability of catalyst, broad applicability to various substrates with good to high yields and a simple operational procedure are the major advantages of the present method. The catalyst can be easily recycled by simple filtration and reused consecutively four times times without significant loss of activity.

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“…It can be easily handled and removed from the reaction mixtures by simple filtration. The recovered Amberlyst‐15 can be reused several times without significant loss of activity …”

Section: Introductionmentioning

confidence: 99%

Amberlyst‐15 as a Green and Efficient Reusable Catalyst for Friedel‐Crafts Alkylation of Activated Arenes with N‐Sulfonyl Aldimines and Synthesis of Bis‐triarylmethanes

Thirupathi¹,

Venkatagiri

Reddy

2018

ChemistrySelect

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“…They possess anti‐allergic, antihypertensive and antibiotic activities . Amino‐substituted tetrazoles have anti‐inflammatory receptor modulator and antiviral activities. These reactions are usually promoted by a Pd‐based catalyst, Pd being a precious metal.…”

Section: Introductionmentioning

confidence: 99%

Application of Pd‐2A3HP‐MCM‐41 to the Suzuki, Heck and Stille coupling reactions and synthesis of 5‐substituted 1H‐tetrazoles

Nikoorazm

Ghorbani‐Choghamarani

Khanmoradi

2016

Applied Organom Chemis

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An ecofriendly heterogeneous catalyst has been synthesized by anchoring palladium onto the surface of organically modified mesoporous silica. The prepared catalyst was characterized using X‐ray diffraction, Fourier transform infrared and energy‐dispersive X‐ray spectroscopies, transmission and scanning electron microscopies, inductively coupled plasma and thermogravimetric techniques. The catalyst shows high activity in the Suzuki, Heck and Stille cross‐coupling reactions and the synthesis of 5‐substituted 1H‐tetrazoles from sodium azide (NaN3). These methods have the advantages of high yields, green reaction conditions, simple methodology and easy separation and workup. Copyright © 2016 John Wiley & Sons, Ltd.

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“…Many homogeneous and heterogeneous catalysts were developed so far to promote [3 + 2]‐cycloaddition reaction for synthesis of tetrazoles including, Zn(II) salts , AlCl 3 , (CH 3 ) 3 Al , Et 3 N.HCl , NH 4 Cl , BF 3 . OEt 2 , TBAF , Pd(PPh 3 ) 4 , Zn/Al hydrotalcite , ZnO , ZnS , Zn–Cu alloy , Cu 2 O , CuFe 2 O 4 nanoparticles , copper triflates , FeCl 3 ‐SiO 2 Fe(OAc) 2 , tungstate salts , CdCl 2 , Sb 2 O 3 , amberlyst‐15 , silica sulfuric acid , montmorillonite K‐10 clay , I 2 , TMSCl , CuFe 2 O 4 nano particles , AgNPs , WAlPO‐5 microspheres , cuttlebone , and CAES . Although many of these catalysts indeed are effective in the synthesis of 1 H ‐tetrazole derivatives, however, the limitations of the existing protocols realized in terms of longer reaction time; harsh reaction conditions; the in situ generation of highly toxic, volatile, and explosive hydrazoic acid; the use of expensive and toxic metal catalysts; formation of stable metal‐tetrazole complexes; tedious work‐ups, and inability or unsatisfactory recovery of catalyst.…”

Section: Introductionmentioning

confidence: 99%

Cu/Graphene/Clay Nanohybrid: A Highly Efficient Heterogeneous Nanocatalyst for Synthesis of New 5‐Substituted‐1H‐Tetrazole Derivatives Tethered to Bioactive N‐Heterocyclic Cores

Rad

Behrouz

Dehchenari

et al. 2016

Journal of Heterocyclic Chem

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A series of new 5‐substituted 1H‐tetrazoles bearing bioactive N‐heterocyclic cores were synthesized through [3 + 2] cycloaddition reactions between alkyl nitriles (RCN) and NaN3 in the presence of Cu/aminoclay/reduced graphene oxide nanohybrid (Cu/AC/r‐GO nanohybrid) as a heterogeneous nanocatalyst in water/i‐PrOH (50:50, V/V) media at reflux condition. The influence of factors on a sample reaction including solvent type, temperature, and catalyst amount was discussed. This current protocol has many advantages including inexpensiveness, environmentally benign, broad substrate scope, excellent yields, and easy work‐up procedure. The Cu/AC/r‐GO used in this protocol is a low‐cost catalyst that proved to have considerable chemical and thermal stabilities. This non‐hygroscopic catalyst can be easily recycled, reused, and stored for many consecutive reaction runs without significant loss in its reactivity.

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Amberlyst-15 catalyzed synthesis of 5-substituted 1-H-tetrazole via [3+2] cycloaddition of nitriles and sodium azide

Cited by 72 publications

References 24 publications

Amberlyst‐15 as a Green and Efficient Reusable Catalyst for Friedel‐Crafts Alkylation of Activated Arenes with N‐Sulfonyl Aldimines and Synthesis of Bis‐triarylmethanes

Amberlyst‐15 as a Green and Efficient Reusable Catalyst for Friedel‐Crafts Alkylation of Activated Arenes with N‐Sulfonyl Aldimines and Synthesis of Bis‐triarylmethanes

Application of Pd‐2A3HP‐MCM‐41 to the Suzuki, Heck and Stille coupling reactions and synthesis of 5‐substituted 1H‐tetrazoles

Cu/Graphene/Clay Nanohybrid: A Highly Efficient Heterogeneous Nanocatalyst for Synthesis of New 5‐Substituted‐1H‐Tetrazole Derivatives Tethered to Bioactive N‐Heterocyclic Cores

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