1660-94-2Relevant articles and documents
Functional bisphosphonate synthesis for the development of new anti-resorption bone drug candidates
Bortolamiol, Enrica,Chiminazzo, Andrea,Sperni, Laura,Borsato, Giuseppe,Fabris, Fabrizio,Scarso, Alessandro
, p. 12641 - 12649 (2019)
Herein we present the synthesis of β-mono and β-bis-substituted vinylidenebisphosphonate esters bearing a carboxylic ester moiety to be used as building blocks for further functionalizations. Reactions of these new bisphosphonate scaffolds through hydrogenation of the unsaturated CC bond and through metal mediated addition of aryl boronic acids and indoles provide a wide range of new bisphosphonate products as potential leads to contrast osteoporosis.
One-Pot, Highly Regioselective 1,3-Dipole Cycloaddition Promoted by Montmorillonite for the Synthesis of Spiro[indole-pyrrolizine], Spiro[indole-indolizine], and Spiro[indole-pyrrolidine] gem -Bisphosphonates
Li, Guozhu,Wu, Mingshu,Liu, Fengjiao,Jiang, Jie
, p. 3783 - 3796 (2015)
Various spiro[indole-pyrrolizine], spiro[indole-indolizine], and spiro[indole-pyrrolidine] gem-bisphosphonates were prepared by multicomponent reactions between isatins, tetraethyl vinylidenebis(phosphonate), and amino acids in the presence of montmorillonite. The one-pot reactions proceeded by 1,3-dipole cycloadditions of azomethine ylides formed in a decarboxylative manner. The proposed mechanism is in line with experimental data that confirmed that the azomethine ylide is formed in a decarboxylative manner; this provides new insight into the underlying mechanisms of such cycloadditions. The method has many notable features, such as a broad substrate scope, high efficiency, and high regioselectivity.
An efficient and facile access to substituted 1e,3e-dienylphosphonates via horner-wadsworth-emmons olefination of α,β-unsaturated aldehydes with tetraethyl methylenebisphosphonate
Yahyaoui, Marwa,Touil, Soufiane,Samarat, Ali
, p. 729 - 731 (2018)
An operationally simple and high-yielding synthetic method for 1E,3E-dienylphosphonates has been developed through the Horner-Wadsworth-Emmons olefination of α,β-unsaturated aldehydes with tetraethyl methylenebisphosphonate, in heterogeneous medium, in th
One-pot alkylidenediphosphorylation of nucleophiles
Grison, Claude,Coutrot, Philippe,Joliez, Stephane,Balas, Laurence
, p. 731 - 735 (1996)
Direct phosphonylalkylidenephosphinylation of nucleophiles is achieved by one-pot mono dialkylphosphonoalkylation of dichlorophosphates or methylphosphonic dichloride followed, in situ, by nucleophilic substitution of the chlorine atom of the alkylidenediphosphorylated intermediate.
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Etienne,Rubini,Bessiere,Walcarius,Grison,Coutrot
, p. 75 - 96 (2000)
Two original acid derivatives of methylene diphosphonic acid (MDP) with two inequivalent phosphorus atoms have been synthesised: [(thiophosphonato)-methyl] phosphonic acid, (MDPS), and [(isopropylamido phosphonato)-methyl] phosphonic acid, (MDPN). A potentiometric study allowed to define the stoechiometry of the complex formed between MDP and magnesium (II) in alcaline medium and a 31P NMR study proved the dissymetric structure of this MDPMg2+ complex. The displacement of the coordination equilibrium between Black Eriochrome T and magnesium (II) permitted to compare the coordination strength of MDP, MDPS and MDPN with the cation Mg2+.
High yield synthesis of tetraethyl alkylenediphosphonates via the Michaelis-Arbuzov reaction
Griffith, Julie A.,McCauley, David J.,Barrans Jr., Richard E.,Herlinger, Albert W.
, p. 4317 - 4323 (1998)
A high-yield synthesis of tetraethyl alkylenediphosphonates was achieved via the Michaelis-Arbuzov reaction. Application of optimized reaction conditions for a series of homologous alkylenediphosphonates establishes the generality of the approach.
Challenging synthesis of bisphosphonate derivatives with reduced steric hindrance
Chiminazzo, Andrea,Sperni, Laura,Fabris, Fabrizio,Scarso, Alessandro
supporting information, (2021/04/12)
An alternative approach is reported for the synthesis of methyl ester protected bisphosphonate building blocks, such as methylene bisphosphonate, vinylidenebisphosphonate and aryl substituted prochiral vinylidenebisphosphonates, that cannot be obtained directly from dimethyl phosphite and dichloromethane.
C-Alkyl-bis-phosphoryl chelating systems for the potential recovery of strategic metals
Babouri, Rachida,Halidou Dougourikoye, Abdoul Razak,Ilagouma, Amadou TidJani,Pirat, Jean-Luc,Virieux, David,Volle, Jean-No?l
, (2020/09/07)
Methylene-bis-phosphonic acid and derivatives are used as complexing agents, diagnostics, therapeutics and show interesting virustatic properties. We describe the syntheses of mono- and di-substituted bisphosphonates and mono- and disubstituted diethyl ((diphenylphosphoryl)methyl)phosphonate as possible chelating systems for the recovery of strategic metals.
