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EnglishCondensation in equimolar amount of o-carboxybenzaldehyde with primary amines, such cyclohexyl and iso-propyl, yields oily products which by subsequent addition of dimethylphosphite produce in very good yield amido-amino-phosphonic acid mono-methyl esters, very soluble in water and in protic organic solvents. The by-product of this addition reaction is a cyclic amino-phosphonic acid dimethyl ester. Characterization of these new compounds is made by NMR spectroscopy (H-1 and P-31), by MS-FAB techniques and IR spectroscopy. A possible reaction mechanism leading to these unexpected products is outlined. Although the phosphorylation reaction is quite complex on the molecular level, this procedure allows to obtained in a very convenient way and by one-pot reaction good yields of aminophosphonic acid mono-methyl esters containing ancillary moieties (the amido group) suitable for complexing metals. Furthermore, in an extended way, the compounds obtained can be thought of as the non-natural analogs of peptides and therefore they can be of utility in biological tests.
| Titolo: | Unexpected course of dimethyl phosphite addition to the condensation products obtained from o-carboxybenzaldehyde and aliphatic amines | |
| Autori interni: | ||
| Data di pubblicazione: | 1995 | |
| Rivista: | ||
| Handle: | http://hdl.handle.net/20.500.11769/30468 | |
| Appare nelle tipologie: | 1.1 Articolo in rivista |
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