Some new derivatives of pyridyl- and quinolylphosphonic acids

Predvoditelev, D. A.; Chukbar, T. G.; Нифантьев, Э. Е.

doi:10.1007/bf00470081

Cited by 2 publications

(2 citation statements)

References 5 publications

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“…Various methods exist for preparing alkyl or aryl substituted heteroaryls 26a-j and the dimethylamino heteroaryls 29a-d. 18 The heteroaryl phosphonic acid bisdimethylamine and phosphonic acid dimethylamide ethyl ester have already been described. 19 However, our method offers a possibility to substitute or vary an already existing phosphonato group.…”

Section: Methodsmentioning

confidence: 99%

N-Heteroarylphosphonates, Part II. Synthesis and Reactions of 2- and 4-Phosphonatoquinolines and Related Compounds

Haase¹,

Günther²,

Görls³

et al. 1999

Synthesis

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We extend our synthetic method for the efficient preparation of dialkoxyphosphoryl-and phosphonio-disubstituted pyridines to include the preparation of other phosphonato substituted N-heterocycles. The key to the success of this method lies in the employment of cationic N-(trifluoromethylsulfonyl)heteroarylium triflates that are activated towards nucleophilic attack. The P(O)(OR) 2 group can be transformed into the P(S)(OR) 2 functionality. We report first attempts to substitute the P(O)(OR) 2 moiety with C-nucleophiles. In addition to our synthetic results, the X-ray structures of two (dimethoxyphosphoryl)trifluoromethanesulfonyldihydro-Nheteroarenes are discussed. We also give complete carbon ( 13 C) and phosphorus ( 31 P)-NMR spectra of a series of 2-and 4-phosphonic ester substituted heteroaryl compounds and their dihydro analogs.Heterocyclic compounds containing P(O)(OR) 2 functionalities in which the phosphorus group is ortho or para to the nitrogen in the heterocycle deserve interest as they have been used to inhibit the corrosion of ferrous metals and can be employed as passive coating agents by dissolving them in the corrosive medium. Examples are brines, weak inorganic acids, CO 2 , H 2 S, etc. These compounds and their derivatives are also employed as additives for sludging and cutting oils, as wetting, rewetting, dispersing and as antistatic agents in the textile and polymer industry. Further useful applications are as emulsifiers for insecticides and agricultural chemical mixtures. 1 In contrast to the corresponding non-quaternized compounds, which show no microbiocidal activity, the quaternized compounds are active as biocides or biostats. These compounds are employed in many areas of industrial chemistry such as bactericides, herbicides, chelating agents, etc. 2 We reported in a recent article 3 that the conclusions drawn from our new synthetic procedure for the preparation of dialkoxyphosphoryl substituted pyridines via N-(trifluoromethylsulfonyl)pyridinium triflates and the appropriate dihydropyridines lead away from the exclusive use of pyridine itself. This procedure profits from the quantitative in situ formation of N-(trifluoromethylsulfonyl)pyridinium triflate, which reacts with P(OR) 3 . 4 The addition of Et 3 N to the reaction mixture transforms the intermediate N-trifluoromethanesulfonyldihydropyridines in to the corresponding 4-phosphonato substituted pyridines. The easy removal of the N-triflyl group then allows the straightforward repetition of this procedure, which finally yields 2,4-bis(dialkoxyphosphoryl)pyridines.In the present article, we report on investigations which tested the influence of steric hindrance (Scheme 1) on the success of our method by employing 3,5-diphenylpyridine (1) and 2,6-diphenylpyridine (5). The di-meta substituted compound 1 reacted as expected to form compound 3, which could be rearomatized to 4 by deprotonation with BuLi. However, the di-ortho substituted compound 5 did not react with Tf-O-Tf 2. Since the electronic properties of the nitrogen atom can...

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Section: Methodsmentioning

confidence: 99%

N-Heteroarylphosphonates, Part II. Synthesis and Reactions of 2- and 4-Phosphonatoquinolines and Related Compounds

Haase¹,

Günther²,

Görls³

et al. 1999

Synthesis

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“…Phosphorus(V)-substituted pyridine was first synthesized by Plazek’s research group [ 46 ] in 1936 by a reaction of 2-dimethylaminopyridine with phosphorus trichloride under oxidative conditions. Later, related compounds were obtained by reactions of metalated pyridines with phosphorus-halogen compounds [ 47 , 48 , 49 ], of pyridinediazonium tetrafluoroborate with phosphorus trichloride [ 50 ], of N -alkoxypyridines with sodium diethyl phosphite and phosphines [ 51 , 52 , 53 , 54 , 55 ], and of N -pyridylpyridines with phosphonic acid [ 56 ], by the Michaelis–Arbuzov reaction [ 57 , 58 ], Pd(II)-catalyzed phosphorylation of halopyridines [ 45 , 59 , 60 ], cyclization of phosphorus-containing 3-azatrienes [ 61 ], and the Diels–Alder reaction involving 3-phosphoryl-1-azadienes [ 62 ]. This section of the review considers recent examples of synthesis of POR 2 -substituted pyridines, including the intramolecular cyclizations of Michael adducts, insertion of carbenoids, formal [2+2+2]-cycloaddition, and phosphorylation reactions ( Figure 1 ).…”

Section: Pyridinesmentioning

confidence: 99%

Synthesis of Phosphorus(V)-Substituted Six-Membered N-Heterocycles: Recent Progress and Challenges

Volkova

Заварзин

2023

Molecules

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Heterocycles functionalized with pentavalent phosphorus are of great importance since they include a great variety of biologically active compounds and pharmaceuticals, advanced materials, and valuable reactive intermediates for organic synthesis. Significant progress in synthesis of P(O)R2-substituted six-membered heterocycles has been made in the past decade. This review covers the synthetic strategies towards aromatic monocyclic six-membered N-heterocycles, such as pyridines, pyridazines, pyrimidines, and pyrazines bearing phosphonates and phosphine oxides, which were reported from 2012 to 2022.

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Some new derivatives of pyridyl- and quinolylphosphonic acids

Cited by 2 publications

References 5 publications

N-Heteroarylphosphonates, Part II. Synthesis and Reactions of 2- and 4-Phosphonatoquinolines and Related Compounds

N-Heteroarylphosphonates, Part II. Synthesis and Reactions of 2- and 4-Phosphonatoquinolines and Related Compounds

Synthesis of Phosphorus(V)-Substituted Six-Membered N-Heterocycles: Recent Progress and Challenges

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