Design and one-pot synthesis of α-aminophosphonates and bis(α-aminophosphonates) by iron(III) chloride and cytotoxic activity

Rezaei, Zahra; Firouzabadi, Habib; Iranpoor, Nasser; Ghaderi, Abbas; Jafari, Mohammad Reza; Jafari, Abbas Ali; Zare, Hamid R.

doi:10.1016/j.ejmech.2009.07.009

Cited by 150 publications

(75 citation statements)

References 35 publications

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“…Than the product was precipitated by adding ice water, filtrated off and washed with cold water. Obtained 1 H, 13 C NMR and FT IR spectral data of all synthesized products were in agreement with published one [35].…”

Section: General Synthetic Proceduressupporting

confidence: 68%

“…1 H-NMR and silica gel Acquired 1 H, 13 C NMR and FT IR spectral data of obtained products were in accordance with published one [36].…”

Section: Experimental Section Materialssupporting

confidence: 49%

“…In this case, as catalysts can be used FeCl 3 [12], ZrCl 4 [13], SbCl 3 /Al 2 O 3 [14], Amberlyst-15 [15], sulfamic acid [16], BF 3 .Et 2 O [17], etc.…”

Section: Introductionmentioning

confidence: 99%

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Kabachnik-Fields and Prins- Ritter Synthesis: Application of Ce(III) Supported on a Weakly Acidic Cation-exchanger Resin in Comparative Study

2015

J Chem Appl

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We described results of comparative studies of the application of Ce(III) cation supported on macroporous weakly acidic polyacrylate resin as catalyst in two model three-component domino syntheses, i.e. Kabachnik-Fields domino synthesis of α-aminophosphonates, and Prins-Ritter domino synthesis of 4-amidotetrahydropyrane derivatives, respectively. It was discovered that cation Ce(III) supported on a weak acid macroporous cation-exchanger shown in the studied reactions at least the same or better catalytic activity as salt CeCl3.7H2O, eventually doped by NaI. Further, we found that reactivity of the low reactive 4-methoxybenzaldehyde as carbonyl compounds in the presence of Ce(III) catalyst increases, while the reactivity of the highly reactive 4-nitrobenzaldehyde in this case strongly decreases due to its low coordination with the catalyst. Finally, the presented synthetic protocols using cerium(III) supported on low-cost industrial resin further increases green impact of studied domino syntheses of α-aminophosphonates, and 4-amidotetrahydropyrane derivatives.

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Section: General Synthetic Proceduressupporting

confidence: 68%

“…1 H-NMR and silica gel Acquired 1 H, 13 C NMR and FT IR spectral data of obtained products were in accordance with published one [36].…”

Section: Experimental Section Materialssupporting

confidence: 49%

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Kabachnik-Fields and Prins- Ritter Synthesis: Application of Ce(III) Supported on a Weakly Acidic Cation-exchanger Resin in Comparative Study

2015

J Chem Appl

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“…16 Lewkowski et al, 17 synthesized bis(α-aminophosphonates) via the phosphite addition to N-(o-substituted phenyl) terephthalic schiff's bases. Bis(α-aminophosphonates) were synthesized by Rezaei et al 18 using aldehydes, diethyl phosphite and diamines in the presence of FeCl 3 catalyst in moderate yields. Lewkowski et al,19 synthesized bis(α-aminophosphonates) via the phosphite addition to imine bearing (R,R) 1,2 diamino cyclohexane moiety whose reactions were diastereoselective.…”

Section: Introductionmentioning

confidence: 99%

Cellulose-SO3H catalyzed synthesis of bis(α-aminophosphonates) and their antioxidant activity

Reddy¹,

Sundar²,

Krishna³

et al. 2017

Org. Commun.

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Abstract:A simple and efficient synthesis of bis(α-aminophosphonates) has been developed by the reaction of aromatic aldehydes, 1,4-phenylenediamine and diethylphosphite in the presence of cellulose-SO 3 H as catalyst under neat conditions at room temperature for 10-30 minutes. The synthesized compounds were screened for their antioxidant activity against DPPH, NO and H 2 O 2 scavenging methods. All the compounds exhibited good to moderate activity.

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“…The key step in the KabachnikÁFields synthesis of 1-aminoalkyl phosphonates is the nucleophilic addition of an amine to a carbonyl compound followed by the addition of a trialkyl or diaryl phosphite to the resulting imines. However, the formation of 1-hydroxy phosphonates or a product of its rearrangement frequently accompanies the formation of 1-aminoalkyl phosphonates, for this method various catalysts are used such as LiClO 4 (12,13) (26), alum (27), and iron(III) chloride (28).…”

Section: Introductionmentioning

confidence: 99%

Potassium dihydrogen phosphate: an inexpensive reagent for the solvent-free, one-pot synthesis of α-aminophosphonates

Joshi

Mandhane

Dabhade

et al. 2010

Green Chemistry Letters and Reviews

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An efficient procedure is described for the synthesis of a-aminophosphonates in the presence of catalytic amount of potassium dihydrogen phosphate (5 mol%) under solvent-free condition at room temperature. Triethyl phosphite reacts with imines (generated in situ from an aldehyde and an amine) to give corresponding coupled products in excellent yields. The present methodology presents several advantages, such as elevated yield, short reaction time, and easy work-up.

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Design and one-pot synthesis of α-aminophosphonates and bis(α-aminophosphonates) by iron(III) chloride and cytotoxic activity

Cited by 150 publications

References 35 publications

Kabachnik-Fields and Prins- Ritter Synthesis: Application of Ce(III) Supported on a Weakly Acidic Cation-exchanger Resin in Comparative Study

Kabachnik-Fields and Prins- Ritter Synthesis: Application of Ce(III) Supported on a Weakly Acidic Cation-exchanger Resin in Comparative Study

Cellulose-SO3H catalyzed synthesis of bis(α-aminophosphonates) and their antioxidant activity

Potassium dihydrogen phosphate: an inexpensive reagent for the solvent-free, one-pot synthesis of α-aminophosphonates

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