Five‐Membered Heterocycles with Four Heteroatoms: Tetrazoles

Tetrazole derivatives are a prime class of heterocycles, very important to medicinal chemistry and drug design due to not only their bioisosterism to carboxylic acid and amide moieties but also to their metabolic stability and other beneficial physicochemical properties. Although more than 20 FDA-approved drugs contain 1H- or 2H-tetrazole substituents, their exact binding mode, structural biology, 3D conformations, and in general their chemical behavior is not fully understood. Importantly, multicomponent reaction (MCR) chemistry offers convergent access to multiple tetrazole scaffolds providing the three important elements of novelty, diversity, and complexity, yet MCR pathways to tetrazoles are far from completely explored. Here, we review the use of multicomponent reactions for the preparation of substituted tetrazole derivatives. We highlight specific applications and general trends holding therein and discuss synthetic approaches and their value by analyzing scope and limitations, and also enlighten their receptor binding mode. Finally, we estimated the prospects of further research in this field.

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“…In solution, the 1 H tautomer is the predominant form, but in the gas phase the 2 H -tautomer is more stable. 1…”

Section: Introductionmentioning

confidence: 99%

“…Interestingly, they have the highest number of nitrogen atoms among the stable heterocycles because pentazoles are highly explosive compounds even at low temperature. 1 The first report of the synthesis of a tetrazole derivative was obtained by the Swedish chemist J. A. Bladin in 1885 at the University of Upsala.…”

Section: Introductionmentioning

confidence: 99%

Tetrazoles via Multicomponent Reactions

2019

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“…The most common of these methods is a 1,3-dipolar cycloaddition reaction between different simple nitrile derivatives and azide ion or hydrazoic acid under pressure. This approach has been more developed using different catalytic systems or altering of substrates during different decades 35 , 40 – 42 . Some recent examples include the use of L-cysteine complex of palladium onto mesoporous channels of MCM-41 43 , Fe 3 O 4 @L-lysine-Pd(0) 43 , copper(I) salt 26 , copper catalyst on biochar nanoparticles 44 , guanidine complex of copper supported on boehmite nanoparticles 45 , zinc(II) salts 46 , Zn/Al hydrotalcite 47 , NiFe 2 O 4 48 , TMSCl and Bu 2 SnO or N -methyl-2-pyrrolidone 49 , FeCl 3 –SiO 2 50 , Amberlyst-15 28 , MCM-41-SO 3 H 51 , 1-disulfo-[2,2-bipyridine]-1,1-diium chloride ionic liquid 52 mainly at elevated temperatures, or dialkyl aluminum azides as the substrate and catalyst 36 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of (E)-2-(1H-tetrazole-5-yl)-3-phenylacrylenenitrile derivatives catalyzed by new ZnO nanoparticles embedded in a thermally stable magnetic periodic mesoporous organosilica under green conditions

Safapoor

Dekamin

Akbari

et al. 2022

Sci Rep

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ZnO nanoparticles embedded in a magnetic isocyanurate-based periodic mesoporous organosilica (Fe3O4@PMO–ICS–ZnO) were prepared through a modified environmentally-benign procedure for the first time and properly characterized by appropriate spectroscopic and analytical methods or techniques used for mesoporous materials. The new thermally stable Fe3O4@PMO–ICS–ZnO nanomaterial with proper active sites and surface area as well as uniform particle size was investigated for the synthesis of medicinally important tetrazole derivatives through cascade condensation and concerted 1,3-cycloaddition reactions as a representative of the Click Chemistry concept. The desired 5-substituted-1H-tetrazole derivatives were smoothly prepared in high to quantitative yields and good purity in EtOH under reflux conditions. Low catalyst loading, short reaction time and the use of green solvents such as EtOH and water instead of carcinogenic DMF as well as easy separation and recyclability of the catalyst for at least five consecutive runs without significant loss of its activity are notable advantages of this new protocol compared to other recent introduced procedures.

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“…The chemistry approach has been achieved. [34][35][36] Sharples and his colleagues reported among the available methods an augmented [3 + 2] ring between an azide and p-toluenesulfonyl cyanide (p-TSCN) under solvent-free conditions and good yields and easy separation [37][38][39][40] . There are disadvantages to all these protocols that have not been applied, given the high toxicity of the materials, the explosive nature, and the low boiling point of hydrazoic acid (37 o C), the use of solvents that contaminant the environment.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of (E)-2-(1H-tetrazole-5-yl)-3-phenylacrylenenitrile Derivatives Under Green Conditions Catalyzed by New Thermally Stable Magnetic Periodic Mesoporous Ognosilica Embedded With ZnO Nanoparticles

Safapoor

Dekamin

Akbari

et al. 2021

Preprint

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ZnO nanoparticles embedded on the surface of magnetic isocyanurate-based periodic mesoporous organosilica (Fe3O4@PMO-ICS–ZnO) was prepared through modified environmental-benign procedure for the first time and was properly characterized by appropriate spectroscopic and analytical methods or techniques used for mesoporous materials. The new thermally stable Fe3O4@PMO-ICS–ZnO materials with proper active sites, uniform particle size and surface area were investigated for the synthesis of medicinally important tetrazole derivatives through cascade condensation and concerted reactions as a representative of the Click Chemistry concept. The desired 5-substituted-1H-tetrazole derivatives were smoothly prepared in high to quantitative yields and good purity under green conditions. Low catalyst loading, very short reaction time and the use of green solvents such as EtOH and water instead of carcinogenic DMF as well as the possibility of easy separation and recyclability of the catalyst for at least five consecutive runs without significant loss of its activity are notable advantages of this new protocols compared to other recent introduced procedures.

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Five‐Membered Heterocycles with Four Heteroatoms: Tetrazoles

Cited by 15 publications

References 92 publications

Tetrazoles via Multicomponent Reactions

Tetrazoles via Multicomponent Reactions

Synthesis of (E)-2-(1H-tetrazole-5-yl)-3-phenylacrylenenitrile derivatives catalyzed by new ZnO nanoparticles embedded in a thermally stable magnetic periodic mesoporous organosilica under green conditions

Synthesis of (E)-2-(1H-tetrazole-5-yl)-3-phenylacrylenenitrile Derivatives Under Green Conditions Catalyzed by New Thermally Stable Magnetic Periodic Mesoporous Ognosilica Embedded With ZnO Nanoparticles

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