Abstract
A series of substituted aminomethylenebisphosphonates is prepared by reaction of dialkyl hydrogen phosphites with triethyl orthoformate and corresponding heteryl- or arylamine. The determining factor in the formation of the target products is appearance of an intermediate associate between the ortho ester and amine. The rate and selectivity of the process can be increased by using a nonpolar solvent to stabilize the transition state of the reaction. Crown ether catalysis increases the selectivity of the process by 10-20%. The synthesized aminomethylenebisphosphonates whose structure was established by NMR spectroscopy exhibit a moderate antibacterial and anticholinesterase activity.
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Krutikov, V.I., Erkin, A.V., Pautov, P.A. et al. Heteryl- and Arylaminomethylenebisphosphonates: Synthesis and Biologic Activity. Russian Journal of General Chemistry 73, 187–191 (2003). https://doi.org/10.1023/A:1024775501781
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DOI: https://doi.org/10.1023/A:1024775501781