LaCl3.7H2O: An efficient catalyst for the synthesis of phosphinates (Michaelis–Arbuzov reaction) under neat conditions and their potential antimicrobial activity

Golla, Madhava; Syed, Rabbani; Katla, Venkata Ramana; Devineni, Subba Rao; Kondapalli, Naresh; Chamarthi, Naga Raju

doi:10.1007/s12039-013-0550-3

Cited by 10 publications

(7 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The Michaelis–Arbuzov reaction can probably be considered the most general method for synthesis of phosphorylpyrimidines known at the moment. Examples of use of the Michaelis–Arbuzov reaction in synthesis of pyrimidinylphosphonates ( Scheme 28 ) were described in several studies [ 125 , 126 , 127 , 128 , 129 ]. Pyrimidines 113 , 115 , 117 , and 119 containing the phosphonate moiety at the 2, 4, 5, or 6 position were obtained by reaction of pyrimidinyl halides 112, 114, 116 , and 118 , respectively, with phosphites.…”

Section: Pyrimidinesmentioning

confidence: 99%

“…Despite more than a century of history, the Michaelis–Arbuzov reaction was relatively recently applied for phosphorylation of pyridazines. Thus, Golla et al [ 128 ] synthesized 2-phosphorylpyrazine 148 from 2-chloropyrazine ( 147 ) and dimethyl phenylphosphonite using LaCl 3 •7H 2 O as the catalyst under neat conditions ( Scheme 37 , line a). Goddard and co-workers [ 131 ] reported an example of using the photo-Arbuzov reaction to prepare dimethyl pyrazine-2-phosphonate 150 from 2-bromopyrazine ( 149 ) and trimethyl phosphite under mild UVA irradiation ( Scheme 37 , line b).…”

Section: Pyrazinesmentioning

confidence: 99%

See 1 more Smart Citation

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

Volkova

Заварзин

2023

Molecules

View full text Add to dashboard Cite

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.

show abstract

Section: Pyrimidinesmentioning

confidence: 99%

Section: Pyrazinesmentioning

confidence: 99%

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

Volkova

Заварзин

2023

Molecules

View full text Add to dashboard Cite

show abstract

“…Gollaet al [ 37 ] developed an innovative solvent-free method to generate phenyl heterocyclic phosphinates as new antimicrobial agents against Gram positive and Gram negative bacteria. After optimization for several reaction conditions, it was concluded that the Lewis acid catalyst LaCl 3 .7H 2 O was the most efficient, leading to high yields.…”

Section: Improvements In and Variations Of The Ma Reactionmentioning

confidence: 99%

Improvements, Variations and Biomedical Applications of the Michaelis–Arbuzov Reaction

Kostoudi

Pampalakis

2022

IJMS

View full text Add to dashboard Cite

Compounds bearing the phosphorus–carbon (P–C) bond have important pharmacological, biochemical, and toxicological properties. Historically, the most notable reaction for the formation of the P–C bond is the Michaelis–Arbuzov reaction, first described in 1898. The classical Michaelis–Arbuzov reaction entails a reaction between an alkyl halide and a trialkyl phosphite to yield a dialkylalkylphosphonate. Nonetheless, deviations from the classical mechanisms and new modifications have appeared that allowed the expansion of the library of reactants and consequently the chemical space of the yielded products. These involve the use of Lewis acid catalysts, green methods, ultrasound, microwave, photochemically-assisted reactions, aryne-based reactions, etc. Here, a detailed presentation of the Michaelis–Arbuzov reaction and its developments and applications in the synthesis of biomedically important agents is provided. Certain examples of such applications include the development of alkylphosphonofluoridates as serine hydrolase inhibitors and activity-based probes, and the P–C containing antiviral and anticancer agents.

show abstract

“…2012 年, 李福伟等 [86] 报道了首个 Pd-催化直接磷酸 2014 年, Chamarthi 等 [88] 以 LaCl 3 •7H 2 O 催化的 Michaelis-Arbuzov 反应, 实现了 C-P 键的偶联(Eq. 68).…”

Section: 磷酸化的苯并噻唑(C-p 键的形成)unclassified

Progress in 2-Position Functionalized Synthesis of 2-Substitutedbenzothiazoles

戴小强¹,

朱亚波²,

汪洲洋³

et al. 2017

Chin. J. Org. Chem.

View full text Add to dashboard Cite

2-Substitutedbenzothiazole derivatives were widely used in chemical, pharmaceutical and agricultural fields. 2-Position functionalized method was a convenient and effective way to synthesize 2-substitutedbenzothiazoles. In this paper, the methods for the synthesis of 2-substitutedbenzothiazoles by the alkylation, acylation, arylation, amination and phosphorylation reactions at the 2-position are reviewed, and their future outlook is also discussed.

show abstract

LaCl3.7H2O: An efficient catalyst for the synthesis of phosphinates (Michaelis–Arbuzov reaction) under neat conditions and their potential antimicrobial activity

Cited by 10 publications

References 22 publications

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

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

Improvements, Variations and Biomedical Applications of the Michaelis–Arbuzov Reaction

Progress in 2-Position Functionalized Synthesis of 2-Substitutedbenzothiazoles

Contact Info

Product

Resources

About