Wydział Chemii

E. Dąbrowska

A. Burzyńska

Artur Mucha

Ewa Matczak-Jon

Wanda Sawka-Dobrowolska

Łukasz Berlicki

Paweł Kafarski

2009

Journal of Organometallic Chemistry

694

3806-3813

10.1016/j.jorganchem.2009.07.025

Naukowa

Angielski

Artykuł

Three-component reaction of a primary amine, diethyl phosphite and triethyl orthoformate followed by acid hydrolysis of the adduct provides N-substituted aminomethylenebisphosphonic acids in good yields. Being extremely versatile, it is commonly utilized for preparation of compounds possessing potential antiosteoporotic, antibacterial, anticancer, antiparasitic or herbicidal activity. However, the mechanism of the reaction remains unknown. p-Nitroaniline has been found an interesting tool to shed light on this matter. Its use allowed to separate and identify four intermediates, both non-phosphorus and phosphorus containing, and subsequently suggest the mechanism of the whole process. The acquired knowledge was helpful in explanation the route and the final product structure obtained for more complex reaction proceeding with the use of 4-aminopyridine. Additional alkylation of the pyridine nitrogen atom, leading to unexpected N-(1-alkylpyridinium-4-amino)methylenebisphosphonic acids was unambiguously proved.

Aminomethylenebisphosphonates, Reaction mechanism, Organophosphorus chemistry

https://doi.org/10.1016/j.jorganchem.2009.07.025

http://www.elsevier.com