Abstract
The reactions of trivalent phosphorus esters, including trialkyl phosphites, dialkyl phosphonites, and alkyl phosphinites, with 3-halo- and 3,4-dihalo-furan-2,5-diones has been shown to lead to the formation of novel phosphorus ylides possessing additional phosphoryl-containing groups. For the reaction of 3,4-dihalo-furan-2,5-diones with trialkyl phosphites, the products are trialkoxyphosphonium ylides containing an adjacent geminal bisphosphonate unit. These can be used to provide a convenient route to novel 2,3,3-tris(dialkoxyphosphoryl)-substituted propionate esters which can be hydrolyzed to give the corresponding novel trisphosphonic monocarboxylic acid.
Highlights
The synthesis of systems containing a geminal bisphosphonate unit has attracted considerable interest because of the ability of some of these systems to bind to the surface of bone or to affect bone metabolism
In our studies of the reactions of trialkyl phosphites with aroyl-5 and heteroaroyl-phosphonates,[6] for example, we have shown that under appropriate conditions the initially produced carbene intermediates can be trapped by phosphite to give novel ylidic phosphonates that can be readily converted into to such geminal bisphosphonates
In this paper we report our studies of the reaction of trialkyl phosphites and other trivalent phosphorus compounds with both mono- and di-halogenated furan-2,5-diones and show how, by reacting trialkyl phosphites with 3,4-dihalofuran-2,5-diones, we have been able to develop a new routes to some novel systems containing the geminal bisphosphonate unit
Summary
The synthesis of systems containing a geminal bisphosphonate unit has attracted considerable interest because of the ability of some of these systems to bind to the surface of bone or to affect bone metabolism. We have studied the reaction of 3-halofuran-2,5-diones with trivalent phosphorus esters, including trialkyl phosphites, dialkyl phosphonites and alkyl phosphinites and have observed the unexpected formation of novel ylidic monophosphoryl compounds. This prompted us to investigate whether we could use dihalogenated furan-2,5-diones to extend this approach to prepare analogous ylidic systems containing a geminal bisphosphoryl unit and, in particular, those containing a geminal bisphosphonate unit. In this paper we report our studies of the reaction of trialkyl phosphites and other trivalent phosphorus compounds with both mono- and di-halogenated furan-2,5-diones and show how, by reacting trialkyl phosphites with 3,4-dihalofuran-2,5-diones, we have been able to develop a new routes to some novel systems containing the geminal bisphosphonate unit
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