A novel and convenient method for synthesis of carbamoyl and thiocarbamoyl phosphonates

Kaboudin, Babak; Zahedi, Hazegh

doi:10.1002/hc.20538

Cited by 26 publications

(9 citation statements)

References 30 publications

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“…The methodology was then expanded to hydrophosphonylation, the addition of a HP(O)(OR) 2 (R = alkyl or aryl) unit across a double bond (Table ). Kaboudin and Zahedi have previously described the catalytic hydrophosphonylation of isocyanates with CaCl 2 , which required chlorinated solvents and column chromatography in the workup . Initial reactions with PhNCO and HP(O)(OEt) 2 in 2-MeTHF showed no conversion at 25 °C and <5% conversion at 60 °C.…”

Section: Resultsmentioning

confidence: 99%

Catalyst-free Hydrophosphinylation of Isocyanates and Isothiocyanates under Low-Added-Solvent Conditions

Huke

Taylor

Argent

et al. 2021

ACS Sustainable Chem. Eng.

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A catalyst-free, low-solvent method for the hydrophosphinylation of isocyanates and isothiocyanates is reported. A range of phosphorus nucleophiles including secondary phosphine oxides HP(O)R 2 (R = Ph, i Pr), phosphites HP(O)(OR) 2 (R = Me, Et), and methyl phenylphosphinate were tested. The procedure tolerated isocyanates and isothiocyanates featuring a wide range of substituents and, with use of 4 equiv of 2-methyltetrahydrofuran (2-MeTHF), solid substrates can be utilized. Twenty-five compounds were prepared with improved functional group tolerance compared to previous methods allowing access to new compounds (16 are novel). Facile scale up and simple reaction conditions make this a straightforward and practical methodology for obtaining phosphorus analogues of ureas and thioureas, which are challenging to synthesize by other methods.

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Section: Resultsmentioning

confidence: 99%

Catalyst-free Hydrophosphinylation of Isocyanates and Isothiocyanates under Low-Added-Solvent Conditions

Huke

Taylor

Argent

et al. 2021

ACS Sustainable Chem. Eng.

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“…[135,136] In the same context, calcium chloride is able to act as a Lewis base catalyst in the reaction of (RO) 2 POH with isocyanates 120 (or isothio-analogue) producing the carbamoyl or thiocarbamoyl phosphonic esters 121. [137][138][139] Other catalysts such as pyridinium halides [PyH] + X -were also applied in similar reactions. [140,141] Failla and Finochiaro reported that carbanilino-phosphonates 123 were obtained from the reaction of α-hydroxyphosphonates 122 (derived from the parent aldehydes and (RO) 2 POH) with phenylisocyanates in the presence of tin octanoate (Scheme 52).…”

Section: Reactions With Isocyanates and Isothiocyanatesmentioning

confidence: 99%

Investigations of the Chemistry of Alkyl Phosphites Toward Nitrogen-Containing Compounds: Efficient Approaches to α-Amino-, β-Amino-, and/or Enaminophosphonates

Abdou

Barghash

Bekheit

2015

Synthetic Communications

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In this study, we report recent investigations of the chemical reactivity of alkyl phosphites mainly trialkyl and dialkyl phosphites with molecules containing different nitrogen-containing compounds reported by us and other research groups over the last twenty five years. Earlier leader important reports were also considered. The reviewed investigations in this article are customized, only according to the type of the nitrogenfunctional groups: [amines (primary, secondary, and tertiary amines), imines, amides, thioamides, nitriles, isocyanates, isothiocyanates, oximes, hydrazones, diazo, and azides]and not according to the site of attack or the final products. Furthermore, the present review article focuses on the synthesis of α-amino-, β-amino-and/or enaminophosphonates. These compounds occupy an important role in pharmaceutical chemistry.2 GRAPHICAL ABSTRACT:

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“…17 Recently, Kaboudin et al reported a expedient method for the synthesis of carbamoyl and carbamothioylphosphonates using CaCl 2 catalyst. 18 However, many of above stated methods have associated with few drawbacks which include using of harsh reaction conditions, long Nowadays, environmental economics has become an important steering wheel for technological innovation. Adopting heterogeneous catalysts in organic reactions are sustainable chemical processes due to better selectivity, cost-effective, operational simplicity and reusability of the catalyst.…”

Section: [Insert Figure 1]mentioning

confidence: 99%

“…, low yield of the product, formation of the side products under catalyst conditions and use of the harmful volatile solvents18 .…”

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confidence: 99%

CeCl₃.7H₂O-SiO₂ Catalyzed Ultrasonicated Solvent-Free Synthesis of Carbamoyl/Carbamothioyl Phosphonates and Antimicrobial Activity Evaluation

Rao

Golla

Syed

et al. 2015

Phosphorus, Sulfur, and Silicon and the Related Elements

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Running head: CeCl 3 .7H 2 O-SiO 2 catalysed solvent-free synthesis for P-C=(O,S) derivatives ABSTRACT An expeditious and green method has been developed for the synthesis of a series of P-C bond derivatives, diethyl substituted phenylcarbamoylphosphonates 6(a-e)/ phenylcarbamothioylphosphonates 7(a-f) in high yields via simple addition reaction of isocyanates/isothiocyanates with diethyl phosphite in the presence of silica supported Lewis acid catalyst, SiO 2 -CeCl 3 .7H 2 O under solvent-free and sonication conditions. The advantages of this method are high yields, avoiding of harmful solvents, operational simplicity, shorter reactiontime, and recoverability and recyclability of the catalyst. Antimicrobial activity was assayed for the title compounds, whereas, the compounds 6c, 7b and 7e against bacteria, and 6a, 7b, 7c and 7e against fungi exhibited potential growth of inhibition.

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A novel and convenient method for synthesis of carbamoyl and thiocarbamoyl phosphonates

Cited by 26 publications

References 30 publications

Catalyst-free Hydrophosphinylation of Isocyanates and Isothiocyanates under Low-Added-Solvent Conditions

Catalyst-free Hydrophosphinylation of Isocyanates and Isothiocyanates under Low-Added-Solvent Conditions

Investigations of the Chemistry of Alkyl Phosphites Toward Nitrogen-Containing Compounds: Efficient Approaches to α-Amino-, β-Amino-, and/or Enaminophosphonates

CeCl₃.7H₂O-SiO₂ Catalyzed Ultrasonicated Solvent-Free Synthesis of Carbamoyl/Carbamothioyl Phosphonates and Antimicrobial Activity Evaluation

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A novel and convenient method for synthesis of carbamoyl and thiocarbamoyl phosphonates

Cited by 26 publications

References 30 publications

Catalyst-free Hydrophosphinylation of Isocyanates and Isothiocyanates under Low-Added-Solvent Conditions

Catalyst-free Hydrophosphinylation of Isocyanates and Isothiocyanates under Low-Added-Solvent Conditions

Investigations of the Chemistry of Alkyl Phosphites Toward Nitrogen-Containing Compounds: Efficient Approaches to α-Amino-, β-Amino-, and/or Enaminophosphonates

CeCl3.7H2O-SiO2 Catalyzed Ultrasonicated Solvent-Free Synthesis of Carbamoyl/Carbamothioyl Phosphonates and Antimicrobial Activity Evaluation

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CeCl₃.7H₂O-SiO₂ Catalyzed Ultrasonicated Solvent-Free Synthesis of Carbamoyl/Carbamothioyl Phosphonates and Antimicrobial Activity Evaluation