Preparation of nitropyridines by nitration of pyridines with nitric acid

Katritzky, Alan R.; Scriven, E. F. V.; Majumder, Suman; Akhmedova, Rena G.; Vakulenko, Anatoliy V.; Akhmedov, Novruz G.; Murugan, Ramiah; Abboud, Khalil A.

doi:10.1039/b413285h

Cited by 45 publications

(22 citation statements)

References 34 publications

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“…Preparation of 2 based on Katrizky methods as follows [10]. Trifluoroacetic anhydride (10 ml, 42 mmol) was chilled in an ice bath and, 17 mmol of pyridines (1) were slowly added and stirred at chilled conditions for 2 h followed by the dropwise addition of concentrated nitric acid (1.9 ml, 36 mmol).…”

Section: Procedures Reaction Synthesis Of 3-nitropyridines (2)mentioning

confidence: 99%

Shortcut Approach to 1,4-Diazepine from 3-Pyridylnitrene Intermedietes under Mild Condition

Ulfa

Okamoto

Satake

2014

J. Pure App. Chem. Res.

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The reaction of nitropyridine derivatives and tributylphosphine (Bu 3 P) with the existence of nucleophilic solvent gives ring expansion product as diazepines in medium yield. Reaction mechanism subjected the formation of phenylnitrene, followed by intramolecular electrophilic insertion reaction to pyridine ring and subsequent ring enlargement. The intermediate in the reaction confirmed by computational calculation using B3LYP/6-31G* level. The intramolecular insertion reaction of pyridylnitrene is considered suppressed by the low HOMO (-9.932 eV) energy level of pyridine ring compared to that of benzene (-9.653 eV), hence 1,4-diazepine is obtained when employed 3-nitro-2,6-lutidine as starting material. The formation of diazepines was confirmed by the analysis of 1 H NMR data. Separation of the product mixture using column chromatography on SiO 2 was carried out and found to give expected diazepine along with the reduction product.

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Section: Procedures Reaction Synthesis Of 3-nitropyridines (2)mentioning

confidence: 99%

Shortcut Approach to 1,4-Diazepine from 3-Pyridylnitrene Intermedietes under Mild Condition

Ulfa

Okamoto

Satake

2014

J. Pure App. Chem. Res.

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“…It has been suggested that the reaction mechanism implies a [1,5] sigmatropic shift of the nitro group. Recently, Katrizky and coworkers [157] have developed an improved method that consists of the in situ generation of dinitrogen pentoxide from nitric acid and trifluoroacetic anhydride (TFAA) (Scheme 16.50).…”

Section: Electrophilic Substitution Reactionsmentioning

confidence: 99%

Six‐Membered Heterocycles: Pyridines

González‐Bello

Castedo

2011

Modern Heterocyclic Chemistry

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Figure 16.5 Examples of agrochemical pyridine derivatives and their applications.1434j 16 Six-Membered Heterocycles: Pyridines IR DataThe pyridine IR spectrum is quite similar to the corresponding vibrations of benzene. Pyridine has C-H stretching frequencies in the range 3020-3070 cm À1 as well as C¼C and C¼N stretching frequencies at 1590-1660 cm À1 and near 1500 cm À1 . N J 2,3 = 4-6 J 2,4 = 0-2.5 J 2,5 = 0-2.5 2 3 4 5 6 J 2,6 = 0-0.6 J 3,4 = 7-9 J 3,5 = 0.5-2 1436j 16 Six-Membered Heterocycles: Pyridines R + Metal catalyst ∆ R = alkyl, vinyl, aryl Scheme 16.2 16.

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“…Dibutyl (2E,2¢E)-3,3¢-(Thiophene-3,4-diyl)diacrylate (69,R 1 =CO 2 Bu); Typical Procedure: [144] The reaction of 3,4-dibromothiophene (68; 0.242 g, 1.00 mmol), butyl acrylate (0.512 g, 4.00 mmol), and K 2 CO 3 (4.00 mmol) at 130 Palladium-containing nanostructured silica 71 bearing trialkyl(4-pyridyl)ammonium binding sites can be used as a heterogeneous catalyst for Heck coupling reactions. This methodology is especially useful because of the easy recovery and reuse of the catalyst.…”

Section: S Brmentioning

confidence: 99%

“…[89][90][91][92][93][94][95][96][97]257] New strategies that have been published include diastereoselective Friedel-Crafts alkylation reactions, e.g. [129] A new method, already successfully applied to the nitration of pyridines and pyridine analogues, [130] has been tested for the direct nitration of thiophenes. [100] Scheme 19 Diastereoselective Friedel-Crafts Alkylation Reactions [98] MeO OH X 2-[1-(4-Methoxyphenyl)-2-nitropropyl]-5-methylthiophene (44,X=NO 2 ); Typical Procedure: [98] 1-(4-Methoxyphenyl)-2-nitropropan-1-ol (106 mg, 0.500 mmol) was placed in a flame-dried flask, dissolved in anhyd CH 2 Cl 2 (10 mL), and cooled to -78 8 8C.…”

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confidence: 99%