Synthesis of 2-aryl-2H-tetrazoles via a regioselective [3+2] cycloaddition reaction

Patouret, Rémi; Kamenecka, Theodore M.

doi:10.1016/j.tetlet.2016.02.102

Cited by 24 publications

(16 citation statements)

References 16 publications

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“…A regioselective synthesis of 2‐aryl‐2 H ‐tetrazoles via silver promoted [3+2] cycloaddition reaction was developed by Kamenecka and co‐workers (Scheme 38). [50] This cycloaddition between arenediazonium salts and trimethylsilyldiazomethane provides 2‐aryl‐5‐trimethylsilyltetrazoles, a key intermediate which can be easily cleaved with CsF to afford 2‐aryl‐2 H ‐tetrazoles in one pot. This transformation tolerates a variety of substituents on the phenyl ring, alkyl‐, alkoxy‐, halo‐, cyano‐, amino‐, acid‐, as well as nitro‐ substituted phenyldiazonium salts and heteroaryl diazonium salts were smoothly converted into the corresponding products in moderate to good yields.…”

Section: Synthesis Of Tetrazolesmentioning

confidence: 99%

Recent Advances in the Synthesis of Nitrogen Heterocycles Using Arenediazonium Salts as Nitrogen Sources

et al. 2020

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Nitrogen heterocycles are important structural subunits that occur widely in bioactive natural products, pharmaceuticals, agrochemicals, dyes, cosmetics, and functional materials. Considering the importance of these useful compounds in modern science, the synthesis of N-heterocycles and their derivatives has always been a hot topic in organic synthesis. Recently, arenediazonium salts which can be easily prepared from inexpensive and abundantly available anilines, have been used as versatile nitrogen sources in the field of nitrogen heterocycle synthetic chemistry due to their ready availability, rich reactivity, and diverse transformations. The aim of the present review is to summarize the recent advances in the synthesis of nitrogen heterocycles using arenediazonium salts as nitrogen sources in the past ten years. Hopefully, it can provide practical guidance for the readers who are interested in utilizing arenediazonium salts as building blocks in organic synthesis. For simplicity and clarity, the organization of this review is based on the number of N atoms in the ring of nitrogen heterocycle.

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Section: Synthesis Of Tetrazolesmentioning

confidence: 99%

Recent Advances in the Synthesis of Nitrogen Heterocycles Using Arenediazonium Salts as Nitrogen Sources

et al. 2020

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“…and co‐authors (Scheme 26). [62] This methodology was demonstrated at gram scale sequence, which was a valuable synthetic building block for the use in drug discovery.…”

Section: Five‐membered Heterocycles Having Four Nitrogen Atomsmentioning

confidence: 99%

Recent advances in the synthesis of five‐ and six‐membered heterocycles as bioactive skeleton: A concise overview

et al. 2022

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Heterocyclic compounds play a tremendous role in the field of medicinal chemistry due to their association with diverse pharmacological properties. Most of the pharmaceutical drugs used in medicines possess a wide range of heterocyclic nucleus. It was decided basis on literature studies that various synthetic protocols like microwave‐assisted, nanocatalysed, green synthesis, click reaction, and multicomponent routes could be used for the betterment of the purity of products, selectivity, and better yields of the products. We have focused attention on the development of synthetic strategies of the above‐mentioned moieties because N‐, O‐ and S‐ containing heterocyclic compounds have seemed owing to a wide diversity of their biological activities viz. antioxidant, anticancer, anticonvulsant, anti‐inflammatory, neuroprotective, antiproliferative, anti‐obesity, antihyperglycemic, antihypercholesteroler, antiulcer, antidiabetic, antileishmanial, antitrypanosomal, antibiotic, etc. In this review article, an overview of the applications of synthetic protocols for the preparation of five‐membered and six‐membered heterocyclic compounds containing two or more heteroatoms (O, N, S) at different‐different positions along with their different potent and competent candidates against various diseases is presented in last 10–15 years.

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“…In a 2016 study by Patouret and Kamenecka, trimethylsilyl diazomethane 42 was involved into this reaction in the presence of CsF to obtain 5-unsubstituted 2-aryltetrazoles 429 [ 216 ]. In this case, CF 3 CO 2 Ag was found to be the silver source of choice.…”

Section: Azoles With Four Heteroatomsmentioning

confidence: 99%

Diazocarbonyl and Related Compounds in the Synthesis of Azoles

et al. 2021

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Diazocarbonyl compounds have found numerous applications in many areas of chemistry. Among the most developed fields of diazo chemistry is the preparation of azoles from diazo compounds. This approach represents a useful alternative to more conventional methods of the synthesis of azoles. A comprehensive review on the preparation of various azoles (oxazoles, thiazoles, imidazoles, pyrazoles, triazoles, and tetrazoles) from diazocarbonyl and related compounds is presented for the first time along with discussion of advantages and disadvantages of «diazo» approaches to azoles.

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Synthesis of 2-aryl-2H-tetrazoles via a regioselective [3+2] cycloaddition reaction

Cited by 24 publications

References 16 publications

Recent Advances in the Synthesis of Nitrogen Heterocycles Using Arenediazonium Salts as Nitrogen Sources

Recent Advances in the Synthesis of Nitrogen Heterocycles Using Arenediazonium Salts as Nitrogen Sources

Recent advances in the synthesis of five‐ and six‐membered heterocycles as bioactive skeleton: A concise overview

Diazocarbonyl and Related Compounds in the Synthesis of Azoles

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