Synthesis of novel aminomethylenebisphosphonates and bisphosphonic acids, containing adamantyl fragment

Minaeva, Lidiya I.; Patrikeeva, L. S.; Kabachnik, M. M.; Beletskaya, I. P.; Orlinson, B. S.; Novakov, I. A.

doi:10.1002/hc.20656

Cited by 20 publications

(5 citation statements)

References 33 publications

(33 reference statements)

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“…The catalyst- and solvent-free methods required long reaction times and/or a high temperature [ 6 – 14 21 – 23 ]. Ionic liquids and a few catalysts were also tried out [ 24 – 27 ], and the synthesis was also described under microwave (MW) irradiation [ 28 – 32 ]. However, most of the MW-assisted syntheses were performed in kitchen ovens [ 28 – 30 ], hence these results cannot be reproduced.…”

Section: Introductionmentioning

confidence: 99%

Microwave-assisted synthesis of (aminomethylene)bisphosphine oxides and (aminomethylene)bisphosphonates by a three-component condensation

Bálint¹,

Tajti²,

Dziełak³

et al. 2016

Beilstein J. Org. Chem.

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SummaryA practical method was elaborated for the synthesis of (aminomethylene)bisphosphine oxides comprising the catalyst- and solvent-free microwave-assisted three-component condensation of primary amines, triethyl orthoformate and two equivalents of diphenylphosphine oxide. The method is also suitable for the preparation of (aminomethylene)bisphosphonates using (MeO)2P(O)H/(MeO)3CH or (EtO)2P(O)H/(EtO)3CH reactant pairs and even secondary amines. Several intermediates referring to the reaction mechanism together with a few by-products could also be identified.

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Section: Introductionmentioning

confidence: 99%

Microwave-assisted synthesis of (aminomethylene)bisphosphine oxides and (aminomethylene)bisphosphonates by a three-component condensation

Bálint¹,

Tajti²,

Dziełak³

et al. 2016

Beilstein J. Org. Chem.

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“…Some modifications of this classic procedure have also been reported. They include the use of a solvent-free, microwave-assisted reaction [69][70][71] and reactions catalyzed by titanium dioxide [72] and by crown ethers (increasing the selectivity of the process by 10%-20%) [73]. Additionally, a reaction carried out in a micellar environment was described [74].…”

Section: Three-component Condensation Of Amines With Triethyl Orthofomentioning

confidence: 99%

Synthetic Procedures Leading towards Aminobisphosphonates

Chmielewska

Kafarski

2016

Molecules

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Abstract:Growing interest in the biological activity of aminobisphosphonates has stimulated the development of methods for their synthesis. Although several general procedures were previously elaborated to reach this goal, aminobisphosphonate chemistry is still developing quite substantially. Thus, innovative modifications of the existing commonly used reactions, as well as development of new procedures, are presented in this review, concentrating on recent achievements. Additionally, selected examples of aminobisphosphonate derivatization illustrate their usefulness for obtaining new diagnostic and therapeutic agents.

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“…29,84 An important variation, with the utilization of trialkyl phosphites [85][86][87] was also reported. Moreover, the biological importance of 1-aminomethylene-1,1-bisphosphonates has prompted the developments of improved methodologies including synthesis under solvent-free conditions, 88 catalytic synthesis, 89 and activation with microwave irradiation. 88,90 …”

Section: Synthesis Via Three-component Reaction Involving An Amine Tmentioning

confidence: 99%

1-Amino-1,1-bisphosphonates. Fundamental syntheses and new developments

Romanenko¹,

Kukhar²

2012

Arkivoc

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1-Amino-1,1-bisphosphonates have become increasingly important in different fields of chemistry, medicine and agriculture. The combination of the unique physical, chemical and biological properties of methylenebisphosphonate and aminophosphonate fragments opens wide possibilities for the design of biologically active compounds including therapeutic agents to treat bone disorders related to calcium metabolism, immunomodulators, anti-infectives and plant growth regulators. The scope of this review is to summarize the existing strategies for the preparation of diversely functionalized 1-amino-1,1-bisphosphonates and to illustrate their utility as synthetic building blocks.

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Synthesis of novel aminomethylenebisphosphonates and bisphosphonic acids, containing adamantyl fragment

Cited by 20 publications

References 33 publications

Microwave-assisted synthesis of (aminomethylene)bisphosphine oxides and (aminomethylene)bisphosphonates by a three-component condensation

Microwave-assisted synthesis of (aminomethylene)bisphosphine oxides and (aminomethylene)bisphosphonates by a three-component condensation

Synthetic Procedures Leading towards Aminobisphosphonates

1-Amino-1,1-bisphosphonates. Fundamental syntheses and new developments

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