Selective C3–H nitration of 2-sulfanilamidopyridines with<i>tert</i>-butyl nitrite

Wang, Hong; Ge, Guo‐Ping; Gao, Wenqing; Luo, Junfei

doi:10.1039/d2qo00679k

Cited by 6 publications

(1 citation statement)

References 46 publications

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“…Because Me-, [24] Cy-, [25] Bn-, [26] F 3 C-, [27] NO-, [28,17] NO 2 -, [29] SCF 3 - [30] are important functional groups in bioactive molecules or drugs, herein, we designed their TEMPO derivatives to investigate the radical releasing reactivities of TEMPO-XR, and the corresponding BDE values are displayed in Scheme 11. According to Scheme 11, it is clear that BDE(OÀ X) scale ranges from 28.0 kcal/mol to 40.1 kcal/mol for 98RT, 99RT, 10RT and 8RT, so the above 4 XRT are assigned as excellent or potential radical donors, i. e. NO * , NO 2 * , Cy * , Bn * .…”

Section: Chemistryselectmentioning

confidence: 99%

Thermodynamic Evaluation on Alkoxyamines of TEMPO Derivatives, Stable Alkoxyamines or Potential Radical Donors?

Qian

Zhang

et al. 2022

ChemistrySelect

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In this work, the bond dissociation energy (BDE) values, including BDE(OÀ X) and BDE(NÀ O), for 129 alkoxyamines (XRT) of TEMPO derivatives were predicted, and the evaluations on stabilities of alkoxyamines, reactivities of alkoxyamines as radical donors and reactivity of TEMPO as various radical scavenger are well compared and discussed based on the predicted BDE values from the view of thermodynamic driving forces. Without a doubt, the wide and valuable BDE values are helpful for chemists better understand the thermodynamic properties and kinetic behaviors of alkoxyamines and TEMPO in chemical reactions and drug metabolism in vivo and promoting the rapid development and application of novel alkoxyamines.

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Section: Chemistryselectmentioning

confidence: 99%

Thermodynamic Evaluation on Alkoxyamines of TEMPO Derivatives, Stable Alkoxyamines or Potential Radical Donors?

Qian

Zhang

et al. 2022

ChemistrySelect

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Dinitropyridines: Synthesis and Reactions

Starosotnikov,

Bastrakov

2024

Asian J Org Chem

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Dinitropyridines are one of the promising classes of heterocyclic compounds. They are considered as useful precursors of explosives and energetic compounds, agrochemicals, biosensors and biologically active compounds with diverse properties: antitumor, antiviral, anti‐neurodegenerative. Preliminary analysis of literature data shows that the chemistry of polynitropyridines has been actively developing over the past few decades. This is evidenced by the steadily growing annual number of publications. In this review the literature on the synthesis, reactions and practical application of isomeric dinitropyridines over a period of 2010‐2024 is analyzed.

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Mechanistic Approach Toward the C4‐Selective Amination of Pyridines via Nucleophilic Substitution of Hydrogen

Choi,

Ham,

van Bonn

et al. 2024

Angewandte Chemie

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The development of site‐selective functionalization of N‐heteroarenes is highly desirable in streamlined synthesis. In this context, direct amination of pyridines stands as an important synthetic methodology, with particular emphasis on accessing 4‐aminopyridines, a versatile pharmacophore in medicinal chemistry. Herein, we report a reaction manifold for the C4‐selective amination of pyridines by employing nucleophilic substitution of hydrogen (SNH). Through 4‐pyridyl pyridinium salt intermediates, 4‐aminopyridine products are obtained in reaction with aqueous ammonia without intermediate isolation. The notable regioselectivity was achieved by the electronic tuning of the external pyridine reagents along with maximization of polarizability in the proton elimination stage. Further mechanistic investigations provided a guiding principle for the selective C–H pyridination of additional N‐heteroarenes, presenting a strategic avenue for installation of diverse functional groups.

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Selective C3–H nitration of 2-sulfanilamidopyridines withtert-butyl nitrite

Abstract: We report a selective C3-H nitration of 2-aminopyridines using the N-sulfonyl group as a directing group. This method provides access to a variety of C3 nitrated 2-sulfanilamidopyridine derivatives. The N-sulfonyl...

Cited by 6 publications

References 46 publications

Thermodynamic Evaluation on Alkoxyamines of TEMPO Derivatives, Stable Alkoxyamines or Potential Radical Donors?

Thermodynamic Evaluation on Alkoxyamines of TEMPO Derivatives, Stable Alkoxyamines or Potential Radical Donors?

Dinitropyridines: Synthesis and Reactions

Mechanistic Approach Toward the C4‐Selective Amination of Pyridines via Nucleophilic Substitution of Hydrogen

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