3-(Ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium cation: A green alternative to tert-butyl nitrite for synthesis of nitro-group-containing arenes and drugs at room temperature

Natarajan, Palani; Chaudhary, Renu; Rani, Neetu; Sakshi, .; Venugopalan, P.

doi:10.1016/j.tetlet.2019.151529

Cited by 14 publications

(8 citation statements)

References 62 publications

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“…HRMS (ESI, m / z ): calculated for C 7 H 8 NO 3 [M + H] + 154.0499, found: 154.0498. Spectral data of the product are in accordance with previously documented data [ 86 ].…”

Section: Methodssupporting

confidence: 84%

Hydroxylation of Aryl Sulfonium Salts for Phenol Synthesis under Mild Reaction Conditions

Hu,

Fu,

Huang

et al. 2024

Molecules

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Hydroxylation of aryl sulfonium salts could be realized by utilizing acetohydroxamic acid and oxime as hydroxylative agents in the presence of cesium carbonate as a base, leading to a variety of structurally diverse hydroxylated arenes in 47–95% yields. In addition, the reaction exhibited broad functionality tolerance, and a range of important functional groups (e.g., cyano, nitro, sulfonyl, formyl, keto, and ester) could be well amenable to the mild reaction conditions.

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“…HRMS (ESI, m / z ): calculated for C 7 H 8 NO 3 [M + H] + 154.0499, found: 154.0498. Spectral data of the product are in accordance with previously documented data [ 86 ].…”

Section: Methodssupporting

confidence: 84%

Hydroxylation of Aryl Sulfonium Salts for Phenol Synthesis under Mild Reaction Conditions

Hu,

Fu,

Huang

et al. 2024

Molecules

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“…108 More recently, a general strategy for the nitration using nitrite-based ionic liquids derived from biodegradable ethyl nicotinate for introduction of the nitro-group containing arene including tolcapone (75) was reported. 109 Scheme 19. Synthesis of Entacapone (63) Opicapone ( 84) is formulated as Ongentys drug product (BIAL-Portela and C a , S.A and Neurocrine Biosciences, San Diego, USA) and used as an adjunctive treatment to levodopa/ carbidopa (3,14) in patients with Parkinson's disease experiencing "off" episodes.…”

Section: Tolcapone (75)mentioning

confidence: 99%

“…More recently, 3,4-dihydroxy-5-nitrobenzoyl chloride ( 77 ) was used to acylate in toluene (Scheme ), leading to tolcapone ( 75 ) . More recently, a general strategy for the nitration using nitrite-based ionic liquids derived from biodegradable ethyl nicotinate for introduction of the nitro-group containing arene including tolcapone ( 75 ) was reported …”

Section: Catechol-o-methyltransferase (Comt) Inhibitors and Their Sy...mentioning

confidence: 99%

Parkinson’s Disease: Advances in Treatment and the Syntheses of Various Classes of Pharmaceutical Drug Substances

Hill,

Huters,

Towne

et al. 2023

Chem. Rev.

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“…In 2020, the Natarajan group reported the development of a new nitrite reagent, 3-(ethoxycarbonyl)-1-[5-methyl-5-(nitrosooxy)hexyl]pyridin-1-ium bistriflimide (TS-N-IL), a greener alternative to tert-butyl nitrite. 74 Moreover, it is less flammable and stable up to 150 °C. TS-N-IL is an ionic liquid, that can be prepared from ethyl nicotinate (143) and 6-bromo-2-methylhexan-2-yl acetate (144) in three steps as shown in Scheme 35.…”

Section: Scheme 34 Aromatic Nitration Using Isoamyl Nitritementioning

confidence: 99%

Organic Nitrating Reagents

Patra¹,

Mosiagin²,

Katayev³

et al. 2022

Synthesis

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Nitro compounds are vital raw chemicals that are widely used in academic laboratories and industries for the preparation of various drugs, agrochemicals, and materials. Thus, nitrating reactions are of great importance for chemists and are even taught in schools as one of the fundamental transformations in organic synthesis. Since the discovery of the first nitrating reactions in the 19th century, progress in this field has been constant. Yet, for many years the classical electrophilic nitration approach using a mixture of strong mineral acids dominated the field. However, in recent decades, the attention of researchers has focused on new reactivity and new reagents that can provide access to nitro compounds in a practical and straightforward way under mild reaction conditions. Organic nitrating reagents have played a special role in this field since they have enhanced reactivity. They also allow nitration to be carried out in an ecofriendly and sustainable manner. This review examines the development and application of organic nitrating reagents.1 Introduction2 Organic Nitrating Reagents2.1 Alkyl Nitrites2.2 Nitroalkanes2.3 Alkyl Nitrates2.4 N-Nitroamides2.5 N-Nitropyrazole2.6 N-Nitropyridinium Salts3 Organic Nitrating Reagents Generated In Situ3.1 Acyl Nitrates3.2 Trimethylsilyl Nitrate3.3 Nitro Onium Salts4 Organic Nitronium Salts5 Organic Nitrates and Nitrites5.1 Ammonium Nitrates5.2 Heteroarylium Nitrates5.3 Other Organic Nitrates5.4 Organic Nitrites6 Conclusion and Outlook

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3-(Ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium cation: A green alternative to tert-butyl nitrite for synthesis of nitro-group-containing arenes and drugs at room temperature

Cited by 14 publications

References 62 publications

Hydroxylation of Aryl Sulfonium Salts for Phenol Synthesis under Mild Reaction Conditions

Hydroxylation of Aryl Sulfonium Salts for Phenol Synthesis under Mild Reaction Conditions

Parkinson’s Disease: Advances in Treatment and the Syntheses of Various Classes of Pharmaceutical Drug Substances

Organic Nitrating Reagents

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