Catalyst-free oxidative N–N coupling for the synthesis of 1,2,3-triazole compounds with<i>t</i>BuONO

Cai, Yueming; Zhang, Xin; An, Cui; Yang, Ye‐Fei; Liu, Wei; Gao, Wenxia; Huang, Xiaobo; Zhou, Yun‐Bing; Liu, Miaochang; Wu, Huayue

doi:10.1039/c9qo00071b

Cited by 25 publications

(11 citation statements)

References 36 publications

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“…The notable characteristicso ft he present methodology are catalyst and additive-free, mild conditions can be scaled up with excellent efficiency (Scheme 111). [140] On the basis of the literature precedents, ap lausible mechanism for the formation of 1,2,3-benzothiadiazolesw as proposed.F irstly,t he substrate 149 (or 149')r eacts with TBN to give an itroso intermediate (A), which on the nucleophilic attack followed by dehydration yields the desired products (Scheme 112).…”

Section: Oximationmentioning

confidence: 99%

“…In 2019, Zhou and Liu group disclosed a catalyst‐free method for the synthesis of diverse 1,2,3‐triazole compounds ( 150 ) via an oxidative N‐N coupling strategy where TBN acts as the nitrogen synthon. The notable characteristics of the present methodology are catalyst and additive‐free, mild conditions can be scaled up with excellent efficiency (Scheme ) …”

Section: Outlines Of the Reactions Involving Tbnmentioning

confidence: 99%

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tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

Dahiya

Sahoo

Alam

et al. 2019

Chemistry An Asian Journal

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The upsurge interesti nt he development of efficient methodologies for the constructiono fn itrogen-containing frameworks via the use of expedient reagents have been creating ar enaissance in contemporary organic chemistry.I nt his perspective, tertbutyl nitrite (TBN) is an emerging building block. Due to its uniques tructuralf eatures, it shows differential reactivity under different reaction conditions. These diverse reactivities have resulted in the construction of ad iverse array of complex N-containing molecules. The primary objective of the presentr eview is to bring the latest findings of TBN in terms of its applications in reactions (oxidation, diazotization, nitrosation, nitration, oximation, N-synthon, and miscellaneous reactions) into the limelight.F or simplicity and brevity,r eactions in each section are explained with the mechanism of formation and selected examples are given.Scheme1.Differential reactivity of TBN. 4455 MinireviewScheme4.Visible-light-promoted synthesis of selenide ethers.Scheme5.Proposed mechanism for visible-light-promoted synthesis of selenide ethers.Scheme6.TBN-mediated synthesis of selenide ethers.Scheme7.Metal-free synthesis of 4-carbonylquinolines.Scheme8.Proposed mechanism for synthesis of 4-carbonylquinolines.Scheme9.TBN-mediated demethylative borylation of methylarenes.Scheme10. Plausible mechanism for demethylative borylation of methylarenes.Scheme11. Trifluoromethylation of various aromatic amine substrates.Scheme12. Copper-catalyzed isoperfluoropropylation of anilines.Scheme13. Plausible mechanism for Cu-catalyzed isoperfluoropropylation of anilines.Scheme14. TBN-mediateddiazotizative allylation of aromatic amines.Scheme15. Oxidativecyanomethylationo fa lkenes via CÀHb ond activation.Scheme16. TBN-mediatedand Cu-catalyzedsynthesis of thioether.

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Section: Oximationmentioning

confidence: 99%

Section: Outlines Of the Reactions Involving Tbnmentioning

confidence: 99%

tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

Dahiya

Sahoo

Alam

et al. 2019

Chemistry An Asian Journal

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“…In 2021 Severin et al reported the functionalization of nitrous oxide for the synthesis of triazolopyridines and triazoloquinolines, 40 which are useful building blocks for heterocycle synthesis. 42–47 The reaction was performed in two steps, the first consisting of the lithiation of 2-alkylpyridine and 2-alkylquinoline derivatives, and the second one involving nitrous oxide for its functionalization to triazolopyridine and triazoloquinoline scaffolds (see Scheme 1), to be compared with other synthesis strategies like those with t BuONO 48 or azides. 49…”

Section: Introductionmentioning

confidence: 99%

A predictive chemistry DFT study of N₂O functionalization for the preparation of triazolopyridine and triazoloquinoline scaffolds

et al. 2022

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“…3). More recently, Wu et al [16] . have prepared [1,2,3]triazolo[1,5‐ a ]pyridines starting from pyridin‐2‐ylmethanamines, through an oxidative catalyst‐free N−N coupling strategy.…”

Section: Introductionmentioning

confidence: 99%

Sequential Organocatalytic Synthesis of [1,2,3]Triazolo[1,5‐a]quinolines

et al. 2020

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In this work, a one-pot sequential organocatalytic method for the synthesis of fused [1,2,3]triazolo [1,5-a]quinolines through successive cyclization and condensation is presented. In this synthetic strategy, the intermolecular [3 + 2]-cycloaddition occurs between 1,3-dicarbonyl compounds and o-carbonyl-substituted phenylazide compounds, for the formation of the 1,2,3-triazole intermediates. Subsequently, an intramolecular condensation reaction generates the fused quinoline ring by the new CÀ C bond formation, giving the products in yields ranging from moderate to excellent. All the reactions were performed using 20 mol% of 1,8diazabicyclo[5.4.0]undec-7-ene (DBU) as catalyst in the presence of DMSO as solvent at 120°C for 24 h and tolerate a range of 1,3-dicarbonyl compounds, such as β-keto esters and 1,3-diketones, and o-formyl, o-acetyl or o-benzoyl substituted phenylazide compounds.

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Catalyst-free oxidative N–N coupling for the synthesis of 1,2,3-triazole compounds withtBuONO

Abstract: A catalyst-free oxidative N–N coupling with tBuONO has been developed for the synthesis of 1,2,3-triazole compounds.

Cited by 25 publications

References 36 publications

tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

A predictive chemistry DFT study of N₂O functionalization for the preparation of triazolopyridine and triazoloquinoline scaffolds

Sequential Organocatalytic Synthesis of [1,2,3]Triazolo[1,5‐a]quinolines

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Catalyst-free oxidative N–N coupling for the synthesis of 1,2,3-triazole compounds withtBuONO

Abstract: A catalyst-free oxidative N–N coupling with tBuONO has been developed for the synthesis of 1,2,3-triazole compounds.

Cited by 25 publications

References 36 publications

tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

tert‐Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

A predictive chemistry DFT study of N2O functionalization for the preparation of triazolopyridine and triazoloquinoline scaffolds

Sequential Organocatalytic Synthesis of [1,2,3]Triazolo[1,5‐a]quinolines

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A predictive chemistry DFT study of N₂O functionalization for the preparation of triazolopyridine and triazoloquinoline scaffolds