Synthesis and NMR Characterization of Two Novel Anthracene-Derived BIS-Aminophosphonates. Basic Hydrolysis of Some Aminophosphonate Derivatives

Abstract

The synthesis of two novel bis-aminophosphonates bearing anthracene rings – bis[N- methyl(diethoxyphosphonyl)-1-(9-anthryl)]benzidine (3) and 4,4′-bis[N-methyl(diethoxy-phosphonyl)-1-(9-anthryl)]diaminodiphenylmethane (4) – via the Kabachnik–Fields reaction is reported. The compounds have been characterized by elemental analysis, TLC, IR, NMR (¹H, ¹³C, ³¹P) and fluorescent spectra. The reaction leads to a mixture of the two possible forms (meso and racemic), with predominant formation of one of the diastereomers. The recrystallized compounds 3 and 4 consist of only one diastereomer. A racemization at the chiral centers and a cleavage of the C-P bond are observed in the alkaline hydrolysis of the new compound 4 and three previously described aminophosphonate derivatives 5–7.

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GRAPHICAL ABSTRACT

Keywords:

• Aminophosphonic acids
• NMR spectroscopy
• basic hydrolysis

ACKNOWLEDGMENTS

Thanks are due to Bulgarian National Science Fund of Ministry of Education and Science for financial support: contract DTK-02/34 (2009).