Mono-nitration of aromatic compounds via their nitric acid salts

Zhang, Pingsheng; Cedilote, Miall; Cleary, Thomas P.; Pierce, Michael E.

doi:10.1016/j.tetlet.2007.10.027

Cited by 20 publications

(8 citation statements)

References 15 publications

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“…It has been described in the literature that nitration in organic solvents can proceed with nitric acid in large excess. 20 The nitronium ion formed by heterolysis of nitric acid as being the active reagent in solution, is under discussion. The NEt 2 substituent favours nitration on the ortho-position due to stabilization of the resonance forms by its lone-pair (para-position is not available) as usually described for anilines and as observed in the present case.…”

Section: Methodsmentioning

confidence: 99%

Further studies on the photoreactivities of ruthenium–nitrosyl complexes with terpyridyl ligands

et al. 2019

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Section: Methodsmentioning

confidence: 99%

Further studies on the photoreactivities of ruthenium–nitrosyl complexes with terpyridyl ligands

et al. 2019

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“…Zhang and co-workers reported that aromatic compounds bearing a basic nitrogen such as 377 can be easily converted into the corresponding nitric acid salts 378 , and in acidic media can further be nitrated resulting in the formation of nitroanilines 379 (Scheme 104 ). 216 In several cases, this two-step procedure provided better yields than the classical nitration using a mixture of nitric and sulfuric acids. In general, yields of this transformation are very high when only one regioisomer is obtained.…”

Section: Organic Nitrates and Nitritesmentioning

confidence: 97%

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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“…Ring formation of the heterocyclic core was accomplished by thermal heating of commercially available benzene-1,2-diamines in neat carboxylic acid . Subsequent regioselective mononitration gave the corresponding 4-nitrobenzimidazoles in good yields, followed by alkylation, arylation, sulfonylation, or acylation reactions to obtain the desired final products. Reactions were regioselective, and the corresponding 1,4-regioisomer products were formed almost exclusively, with only small amounts of the corresponding 1,7-regioisomers observed as alkylation side-products.…”

Section: Chemistrymentioning

confidence: 99%

Discovery of the First Potent and Selective Inhibitors of Human dCTP Pyrophosphatase 1

et al. 2016

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The dCTPase pyrophosphatase 1 (dCTPase) regulates the intracellular nucleotide pool through hydrolytic degradation of canonical and noncanonical nucleotide triphosphates (dNTPs). dCTPase is highly expressed in multiple carcinomas and is associated with cancer cell stemness. Here we report on the development of the first potent and selective dCTPase inhibitors that enhance the cytotoxic effect of cytidine analogues in leukemia cells. Boronate 30 displays a promising in vitro ADME profile, including plasma and mouse microsomal half-lives, aqueous solubility, cell permeability and CYP inhibition, deeming it a suitable compound for in vivo studies.

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Mono-nitration of aromatic compounds via their nitric acid salts

Cited by 20 publications

References 15 publications

Further studies on the photoreactivities of ruthenium–nitrosyl complexes with terpyridyl ligands

Further studies on the photoreactivities of ruthenium–nitrosyl complexes with terpyridyl ligands

Organic Nitrating Reagents

Discovery of the First Potent and Selective Inhibitors of Human dCTP Pyrophosphatase 1

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