An efficient synthesis of N-nitrosamines under solvent, metal and acid free conditions using tert-butyl nitrite

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

doi:10.1039/c5gc02880a

Cited by 87 publications

(40 citation statements)

References 77 publications

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“…disclosed a method for the nitrosation of secondary amines ( 39 ) under transition‐metal, solvent, and acid‐free conditions. In this protocol, anilines having a variety of functional groups irrespective of steric and electronic effects were smoothly converted to their respective N ‐nitroso product (Scheme ) …”

Section: Outlines Of the Reactions Involving Tbnmentioning

confidence: 99%

“…In this protocol, anilines having av ariety of functional groupsi rrespectiveo fs teric and electronic effectsw ere smoothly converted to their respective N-nitroso product (Scheme 29). [58] N-nitroso push-pull dyes are important and uncommon NO donors, in which the release of NO is prompted by light and complemented by as imultaneous fluorescencet urn-on. In 2018, Qiang and Yang group together reported dealkylative Nnitrosation of tertiarya mines using TBN as the nitrosating agent under am etal-free condition.…”

Section: Nitrosationmentioning

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: Nitrosationmentioning

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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“…To the best of our knowledge organosilanes have not been explored in denitrosation reactions. In continuation of our previous works on N ‐nitrosamine chemistry, here we report an efficient method for the denitrosation of aryl‐ N ‐nitrosamines using an iodine‐triethylsilane system (Scheme ).…”

Section: Methodsmentioning

confidence: 91%

An Efficient Metal‐Free Method for the Denitrosation of Aryl N‐Nitrosamines at Room Temperature

et al. 2017

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A simple and practical method for the denitrosation of aryl N-nitrosamines to secondary amines is reported under metal-free conditions using iodine and triethylsilane. Several reductionsusceptible functional groups such as alkene, alkyne, nitrile, nitro, aldehyde, ketone and ester were found to be very stable during the denitrosation, which is remarkable. Broad substrate scope, room temperature reactions and excellent yields are the additional features of the current methodology.

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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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An efficient synthesis of N-nitrosamines under solvent, metal and acid free conditions using tert-butyl nitrite

Abstract: N-Nitrosation of secondary amines was accomplished in an efficient manner using tert-butyl nitrite under solvent, metal and acid free conditions.

Cited by 87 publications

References 77 publications

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

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

An Efficient Metal‐Free Method for the Denitrosation of Aryl N‐Nitrosamines at Room Temperature

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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