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

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ABSTRACT

A 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.

No MeSH data available.


Synthetic methods for (aminomethylene)bisphosphine oxides.
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C4: Synthetic methods for (aminomethylene)bisphosphine oxides.

Mentions: (Aminomethylene)bisphosphine oxides are analogous to (aminomethylene)bisphosphonates, but they are much less studied. Only a few publications were found, which focus on their synthesis [33,39–42], however, a three-component condensation has not been described. They can also be prepared starting from dimethylformamide dimethyl acetal, as in the synthesis of (aminomethylene)bisphosphonates, but in the latter case a secondary phosphine oxide is the P-reagent [33,39]. In addition, (aminomethylene)bisphosphine oxides can be synthesized by the reaction of two molecules of (dialkylamino)(diphenylphosphinoyl)chloromethane (Scheme 4) [40–41], or by the addition of diphenylphosphine oxide to an isonitrile (Scheme 4) [36,42].


Microwave-assisted synthesis of (aminomethylene)bisphosphine oxides and (aminomethylene)bisphosphonates by a three-component condensation
Synthetic methods for (aminomethylene)bisphosphine oxides.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC4979732&req=5

C4: Synthetic methods for (aminomethylene)bisphosphine oxides.
Mentions: (Aminomethylene)bisphosphine oxides are analogous to (aminomethylene)bisphosphonates, but they are much less studied. Only a few publications were found, which focus on their synthesis [33,39–42], however, a three-component condensation has not been described. They can also be prepared starting from dimethylformamide dimethyl acetal, as in the synthesis of (aminomethylene)bisphosphonates, but in the latter case a secondary phosphine oxide is the P-reagent [33,39]. In addition, (aminomethylene)bisphosphine oxides can be synthesized by the reaction of two molecules of (dialkylamino)(diphenylphosphinoyl)chloromethane (Scheme 4) [40–41], or by the addition of diphenylphosphine oxide to an isonitrile (Scheme 4) [36,42].

View Article: PubMed Central - HTML - PubMed

ABSTRACT

A 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.

No MeSH data available.