Synthesis of Novel Functionalized gem-Bisphosphonates.-Michael-type addition of the masked polyfunctional nucleophiles (II) to tetraethyl ethylidenebisphosphonate (I) produces the gem-bisphosphonates (III). The compounds (IIIb) and (IIId) are deprotected yielding the primary amines (IV). The carboxylic acid (V) is obtained by ester saponification of (IIIa) followed by thermal decarboxylation of the dicarboxylic acid formed. Reaction of potassium cyanide (VI) with (I) gives 3,3-bis(diethoxyphosphoryl)propionitrile (VII). The compounds (III) -(V), and (VII) are potentially useful in the therapy of bone tissues. -(STURTZ, G.; GUERVENOU, J.; Synthesis (1991) 8, 661-662; Lab. Chim. Heteroorg., UFR Sci. Techn., 29287 Brest, Fr.; EN)
The preparation of a.P unsaturated monophosphonate heterocycles is reported. 9-diethylphosphono-7-oxabicyclo[4.3.0]non-1(9)-ene, some 3-diethylphosphono-2H-1-benzopyrans and 2-diethylphosphono-3H-naphtol[2,1-b]pyran have been prepared from tetraethyl ethylidene gem-bisphosphonate and 2-hydrocyclohexanone, substituted salicylaldehydes or 2-hydroxy-1-naphthaldehyde respectively.
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