First synthesis of 1,1′-ferrocene bis-aminophosphonic esters

Lewkowski, J.; Rzeźniczak, Monika; Skowroński, R.

doi:10.1016/j.jorganchem.2004.01.012

Cited by 5 publications

(2 citation statements)

References 36 publications

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“…Lewkowski and co-workers [58][59][60] synthesized and fully characterized some ferrocenyl aminophosphonates. Their method for the synthesis of these compounds involves two steps.…”

Section: Introductionmentioning

confidence: 99%

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An Efficient and Eco-Friendly Nanocrystalline Zinc Oxide Catalyst for One-Pot, Three Component Synthesis of New Ferrocenyl Aminophosphonic Esters Under Solvent-Free Condition

Hosseini‐Sarvari

2010

Catal Lett

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An eco-friendly catalytic amount (10 mol%) of nanocrystalline ZnO has been explored in the synthesis of new series of ferrocenyl aminophosphonic esters by a three-component reaction of ferrocene carbaldehyde, an amine, and a dialkyl phosphate. The nano ZnO catalyzed the selective synthesis of ferrocenyl aminophosphonates and no intermediate formation of either an imines or a-hydroxy phosphonate were observed. This is one of the fundamental aspects in green chemistry for simple experimental and product isolation protocol.

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“…Lewkowski and co-workers [58][59][60] synthesized and fully characterized some ferrocenyl aminophosphonates. Their method for the synthesis of these compounds involves two steps.…”

Section: Introductionmentioning

confidence: 99%

“…To the best of our knowledge, this is the first report on the use of nano crystalline ZnO catalyst for the synthesis of new ferrocenyl aminophosphonates. These compounds may eventually show potential properties as plant-protection agents or antitumor drugs, as Lewkowski and co-workers [58][59][60] claimed.…”

Section: Introductionmentioning

confidence: 99%

An Efficient and Eco-Friendly Nanocrystalline Zinc Oxide Catalyst for One-Pot, Three Component Synthesis of New Ferrocenyl Aminophosphonic Esters Under Solvent-Free Condition

Hosseini‐Sarvari

2010

Catal Lett

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A simple synthesis of ferrocenyl bis-amides by a Ugi four-component reaction

Akbarzadeh

Mirzaei

Bazgir

2010

Journal of Organometallic Chemistry

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Synthesis, structure and assessment of the cytotoxic properties of 2,5-dimethylazaferrocenyl phosphonates

et al. 2006

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The reaction of lithiated 2,5-dimethylazaferrocene 1 with diethyl chlorophosphate proceeds to give lateral and ring phosphonate products. The products 2 and 3 were characterized by spectroscopic (1H, 31P{1H} NMR, MS, IR) methods and 3 was treated with W(CO)5(thf) to form a crystalline W(CO)5-complex 4 which was characterized by single-crystal X-ray analysis. The new 2,5-dimethylazaferrocenyl phosphonates were transformed into the corresponding N-methyl iodide salts 5 and 6 in quantitative yields. Both salts are water soluble and stable compounds and an analysis of their cytotoxic and anti-proliferative activity was carried out. Compound 6 possesses anti-metabolic activity which exhibited some preference towards the cancerous HeLa cell line over the non-cancerous NIH 3T3 cell line. These new compounds are the first examples of azaferrrocene (i.e. non-ferrocene) derivatives featuring biologically important phosphonate groups. The preliminary studies into cytotoxic activity indicates that as with ferrocene, azaferrocene can also be regarded as a potential source for organometallic anticancer agents, featuring the iron centre in the +2 oxidation state rather than the often utilized ferrocenium +3 species.

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First synthesis of 1,1′-ferrocene bis-aminophosphonic esters

Cited by 5 publications

References 36 publications

An Efficient and Eco-Friendly Nanocrystalline Zinc Oxide Catalyst for One-Pot, Three Component Synthesis of New Ferrocenyl Aminophosphonic Esters Under Solvent-Free Condition

An Efficient and Eco-Friendly Nanocrystalline Zinc Oxide Catalyst for One-Pot, Three Component Synthesis of New Ferrocenyl Aminophosphonic Esters Under Solvent-Free Condition

A simple synthesis of ferrocenyl bis-amides by a Ugi four-component reaction

Synthesis, structure and assessment of the cytotoxic properties of 2,5-dimethylazaferrocenyl phosphonates

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