Bromination of some pyridine and diazine N-oxides

Paudler, William W.; Jovanovic, Misa V.

doi:10.1021/jo00155a027

Cited by 45 publications

(28 citation statements)

References 5 publications

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“…A: To a solution of Pyridinium N-(2'-pyridyl)aminide (1) (1 mmol) in dichloromethane (5 mL) stirred at -20°C a solution of the corresponding NXS (1 mmol) in the same solvent (10 mL) was added dropwise. After 1 hour of stirring, the solvent was evaporated and the residue was purified by column chromatography on silica gel with ethanol as eluent.…”

Section: Halogenation Of Pyridinium Aminides Methodsmentioning

confidence: 99%

Halogenation of pyridinium-N-(2′-pyridyl)aminide: An easy synthesis of halo-2-aminopyridines

et al. 1995

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Section: Halogenation Of Pyridinium Aminides Methodsmentioning

confidence: 99%

Halogenation of pyridinium-N-(2′-pyridyl)aminide: An easy synthesis of halo-2-aminopyridines

et al. 1995

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“…An oxo substituent at the 5-position is sufficiently activating to permit the 6-bromination of some 1,2,4-triazin-5-ones and -3,5-diones [183]. Although the presence of an N-oxide function proved insufficient to allow chlorination and bromination, both the 3-amino-and 3-methoxy-1,2,4-triazine 1-or 2-oxides gives 6-halogeno derivatives [321][322][323].…”

Section: Thermal and Photochemical Reactionsmentioning

confidence: 99%

Six‐Membered Heterocycles: Triazines, Tetrazines and Other Polyaza Systems

Oliva¹,

Laza²,

Ocáriz³

2011

Modern Heterocyclic Chemistry

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“…The mixture is extracted with 300 ml of CCl 4 in a Soxhlet extractor for 2 h. After evaporation of the CCl 4 , a white precipitate (9.33 g) is obtained, which is recrystallized from 45 ml of EtOH. Yield 6.9 g (55%); mp 167-170C [16]. Found, %: C 23.64; H 2.12; N 11.11.…”

Section: 5-dibromopyridine-4-amine (3)mentioning

confidence: 99%

Synthesis of pyridinium betaine azo chromophores

Kreicberga

Laipniece

Bērziņa

et al. 2010

Chem Heterocycl Comp

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New chromophores have been synthesized and investigated containing as acceptor a quaternized pyridine unit with mobile bromine in the structure conjugated with two donor units -the indan-1,3-dione anion and the dihydroxyethylamino group through a -conjugated spacer.Organic nonlinear optical (NLO) materials have the potential for various applications in the field of optical signal processing, giving the impulse to design more and more chromophores with enhanced NLO properties [1].Among the most investigated subjects are azobenzene derivatives particularly "push-pull" azobenzenes with asymmetric electron distribution because of the substitution pattern at the 4 and 4' positions with electron-releasing (donor, D) and electron-withdrawing (acceptor, A) groups. Due to their large dipole moments and photochemistry (trans to cis isomerization), they have been investigated as components for NLO devices, lithography, all-optical switches, and data storage [2]. Incorporation of the π-deficient pyridine moiety as acceptor by noncovalent interactions (hydrogen bonds) gives additional advantage to obtain liquid crystals [3], liquid crystalline polymers [4], proton-responsive photo switches [5], and three-dimensional octupolar structures by complexation to transition metals [6].Azopyridine-based chromophores could be bound covalently to functionalized surfaces by reaction with alkyl-or benzyl halides, simultaneously creating the pyridinium group [7,8]. Quaternization of pyridine provides a way of enhancing its acceptor capability. Recently, potential NLO and electro-optical properties have been demonstrated for several pyridinium intramolecular salts [9, 10], including N-(1,3-dioxoindan-2-yl)pyridinium betaine (IPB) [11].In order to extend the scope of compounds with NLO activity, we aim to synthesize the dual chromophore 1 by linking the azopyridine-based chromophore with IPB via the common pyridinium moiety. The dioxyethylamino substituent in compound 1 makes it useful for synthesis of polymers. The constitution of molecule 1 can be described by two important mesomeric formulas: C O O N N N R N CH 2 CH 2 OTHP CH 2 CH 2 OTHP 1 a-c a R = R 1 = Br, b R = Br, R 1 = CN, c R = R 1 = Ph THP = tetrahydro-2H-pyran-2-yl O O N N N R

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Bromination of some pyridine and diazine N-oxides

Cited by 45 publications

References 5 publications

Halogenation of pyridinium-N-(2′-pyridyl)aminide: An easy synthesis of halo-2-aminopyridines

Halogenation of pyridinium-N-(2′-pyridyl)aminide: An easy synthesis of halo-2-aminopyridines

Six‐Membered Heterocycles: Triazines, Tetrazines and Other Polyaza Systems

Synthesis of pyridinium betaine azo chromophores

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