Metal free organic transformation: cyanuric chloride catalyzed synthesis of 5-substituted-1H-tetrazoles

doi:10.1016/j.tetlet.2015.03.032

Tetrahedron Letters

Volume 56, Issue 17, 22 April 2015, Pages 2203-2206

https://doi.org/10.1016/j.tetlet.2015.03.032 Get rights and content

Highlights

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TCT is stable, inexpensive, commercially available and easy to handle catalyst.
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Operational simplicity and activity under mild reaction conditions.
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Excellent product yields with greater substrate scope.

Abstract

A wide variety of nitriles react with sodium azide in the presence of a catalytic amount of cyanuric chloride or 2,4,6-trichloro-1,3,5-triazine (TCT) under mild reaction conditions to give the corresponding 5-substituted-1H-tetrazoles in good to excellent yields. Here, we used TCT as a source of hydrochloric acid to catalyze this cycloaddition reaction.

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Acknowledgment

The authors thank the Council of Scientific and Industrial Research (No. 02(0025)/11/EMR-II), New Delhi, India for financial support.

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Cited by (22)

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2023, Journal of Heterocyclic Chemistry
Cyanuric chloride, a chlorinated analog of 1,3,5‐triazine, is used as a catalyst, promoter, and activator to catalyze and initiate several reactions like Beckmann rearrangement, Lossen rearrangement, Biginelli reaction, Suzuki coupling reaction, Pictet Spengler reaction, Mannich reaction, etc. It is employed in several reactions due to its several properties like stable, non‐volatile, cost‐efficient, easy to handle, and easy commercial availability. Moreover, it is a very renowned precursor for the synthesis of triazine‐class pesticide atrazine, dyes, and crosslinking agents. Herein in this review article, the reactions initiated, catalyzed, and promoted by cyanuric chloride from 2010 to 2022 have been elaborated.
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2023, Synthetic Communications
Cyanuric chloride is regarded as the green source for the in situ generation of hydrochloric acid. It is a metal-free, eco-friendly, inexpensive, and commercially available organocatalyst. This fascinating organocatalyst was found efficient to carry out diverse organic transformations. Many biologically active heterocylic scaffolds were synthesized using cyanuric chloride as catalyst. As a result, during last two decades it has gained significant attention. In this review, we have summarized various organic transformations for the synthesis of structurally diverse biologically promising scaffolds utilizing cyanuric chloride as an efficient metal-free organocatalyst.
Synthesis, molecular docking and xanthine oxidase inhibitory activity of 5-aryl-1H-tetrazoles
2018, Bioorganic Chemistry
Citation Excerpt :
Some encouraging results were observed (Table 1), which are discussed in the forthcoming paragraphs. Compounds 1, and 5 are new compounds, while the remaining compounds were identified as previously reported compounds [43–61]. Twenty-four derivatives of 5-aryl-1H-tetrazole (1–24) were synthesized by mixing sodium azide, ammonium chloride, and differently substituted nitrile derivatives in dimethyl formamide (DMF) under refluxing conditions (Scheme1).
5-Aryl-1H-tetrazoles (1–24) were synthesized and screened for their xanthine oxidase (XO) inhibitory activity using allopurinol as standard inhibitor (IC₅₀ = 2.0 ± 0.01 µM). Six compounds 3, 4, 5, 9, 21, and 24 exhibited significant to weak activities with IC₅₀ values in the range of 7.4–174.2 µM. Active compounds were further subjected to kinetic and molecular docking studies to deduce their modes of inhibition, and to study their interactions with the protein (XO) at atomic level, respectively. Interestingly, all these compounds showed a competitive mode of inhibition. Docking studies identified several important interactions between the ligand and the receptor protein (XO). Some of these interactions were similar to that exhibited by clinical inhibitors of XO (allopurinol, and febuxostat). This study identifies 5-aryl-1H-tetrazoles as a new class of xanthine oxidase inhibitors, which deserves to be further, investigated for the treatment of hyperuricemia and gout.
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Diisopropylethylammonium acetate (DIPEAc): An efficient and recyclable catalyst for the rapid synthesis of 5-substituted-1H-tetrazoles
2017, Synthetic Communications
A simple and efficient protocol developed for the synthesis of 5-substituted 1H-tetrazole derivatives through [2+3] cycloaddition reaction between benzonitriles and sodium azide using diisopropylethylammonium acetate as a recyclable reaction medium is described. The reactions proceed well at 80 °C and provide the corresponding tetrazoles in good to excellent yields (up to 94% yield). Developed method has notable advantages, such as simple and mild conditions, easy workup, reusability with consistent catalytic activity, and safer alternative to hazardous, corrosive conventional Lewis acid catalysts.

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Metal free organic transformation: cyanuric chloride catalyzed synthesis of 5-substituted-1H-tetrazoles

Highlights

Abstract

Graphical abstract

Section snippets

Acknowledgment

Bioorg. Med. Chem.

J. Med. Chem.

J. Org. Chem.

Tetrahedron Lett.

Tetrahedron Lett.

Tetrahedron Lett.

Tetrahedron Lett.

Mater. Lett.

Tetrahedron Lett.

Tetrahedron Lett.

Org. Biomol. Chem.

J. Med. Chem.

Tetrahedron Lett.

Catal. Commun.

Synth. Commun.

Tetrahedron

J. Mol. Struct.

Targets Heterocycl. Syst.

Proc. Int. Pyrotech. Semin.

J. Heterocycl. Chem.

Bioscience

Tetrahedron Lett.