Regioselective Nitration of <i>N</i>-Alkyl Anilines using <i>tert</i>-Butyl Nitrite under Mild Condition

Chaudhary, Priyanka; Gupta, Shipra Sen; Muniyappan, N.; Sabiah, Shahulhameed; Kandasamy, Jeyakumar

doi:10.1021/acs.joc.8b02377

Cited by 40 publications

(14 citation statements)

References 44 publications

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“…Herein, TBN concomitantly acts as both a nitrosating and a nitration agent. The synthesized products were further transformed to N ‐alkyl phenylenediamines and N ‐alkyl nitroanilines using Zn/AcOH and 25 % aqueous HCl in methanol, respectively (Scheme ) . In 2015, Li and co‐workers reported a direct and eco‐friendly oxy‐nitration method for the synthesis of 3‐nitroquinoline N ‐oxides ( 68 ) from quinoline N ‐oxides ( 67 ) and TBN.…”

Section: Outlines Of the Reactions Involving Tbnmentioning

confidence: 99%

“…The synthesized products were further transformed to N-alkyl phenylenediamines and N-alkyl nitroanilines using Zn/AcOH and 25 %a queous HCl in methanol, respectively (Scheme 49). [75] In 2015, Li andc o-workersr eported ad irect and eco-friendly oxy-nitrationm ethod for the synthesis of 3-nitroquinoline N-oxides (68)f rom quinoline N-oxides (67)a nd TBN. The chemoselective nature of this transformationi sd ue to the electrophilic nature of NO 2 radicala nd highere lectron density at the C3 positiono fn itroquinoline N-oxides (Scheme 50).…”

Section: Nitrationmentioning

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: Outlines Of the Reactions Involving Tbnmentioning

confidence: 99%

Section: Nitrationmentioning

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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“…Eventually, denitrozation by HCl in CH 3 OH produce nitrated N‐alkyl aniline. In addition, authors also observed that Anilines bearing electron‐donating groups (e. g. methyl and methoxy) as well as electron‐withdrawing groups (such as chlorine and bromine) underwent ring nitration smoothly and gave 72–84 % yields ortho nitrated products within above 3 hours [49] …”

Section: Nitration By Transition Metal‐free Catalystmentioning

confidence: 99%

Synthetic Protocols for Aromatic Nitration: A Review

Patel

2021

ChemistrySelect

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Nitration of aromatic compounds represents a powerful and widely used transformation that allows introducing nitro group into aromatic systems. New synthetic strategies for aromatic nitration are deeply needed, including highly efficient and selective nitration methods. Aromatic nitration plays an important part in the industry, as the main use of nitration is to produce important products such as dyes & intermediate compounds, drugs, and Agrochemicals. The electrophilic aromatic nitration is most studied and important transformation in industrial process. This review will describe different possible methodologies that apply to this fundamental transformation with special attention to the most recent development that lasted from 2017–2020. The main pros and cons of recent nitration methods are briefly described with their specific reaction mechanism and highlighting the most important feature of the present aromatic nitration method.

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“…9c,d Other advantages of TBN are its low cost and commercially availability, and the fact that it is economic and easy to store and handle. We have recently demonstrated different applications of tert-butyl nitrite in organic synthesis, including N-nitrosation of secondary amines, 11 oxidative dimerization of thioamides, 12 conversion of o-phenylenediamines into triazoles, 13 nitration of Nalkyl anilines 14 and one-pot transamidation of secondary amides. 15 In continuation of this work, we herein report the palladium-catalyzed one-pot synthesis of 2,3-deoxy 3-keto aryl C-glycosides from glycals and anilines in the presence of tert-butyl nitrite under mild conditions (Scheme 1).…”

Section: Paper Syn Thesismentioning

confidence: 99%

Palladium-Catalyzed One-Pot Stereospecific Synthesis of 2-Deoxy Aryl C-Glycosides from Glycals and Anilines in the Presence of tert-Butyl Nitrite

Singh¹,

Venkatesh²,

Kandasamy

2019

Synthesis

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The palladium-catalyzed one-pot synthesis of 2,3-deoxy-3-keto aryl C-glycosides is achieved from glycals and anilines in the presence of tert-butyl nitrite and aqueous HBF4 under mild conditions. This one-pot method stereospecifically provides α- and β-aryl glycosides (≥19:1 by NMR) in good yields at room temperature. The configuration at the C-3 position in the glycal determines the anomeric selectivity (i.e., α or β) of the desired products.

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Regioselective Nitration of N-Alkyl Anilines using tert-Butyl Nitrite under Mild Condition

Cited by 40 publications

References 44 publications

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

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

Synthetic Protocols for Aromatic Nitration: A Review

Palladium-Catalyzed One-Pot Stereospecific Synthesis of 2-Deoxy Aryl C-Glycosides from Glycals and Anilines in the Presence of tert-Butyl Nitrite

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