1-aminophosphonic acids and esters bearing heterocyclic moiety. Part 2. 1 pyridine, pyrrole and emidazole derivatives

Article abstract of DOI:10.1080/10426509608046390

The benzylic amines (benzylamine, benzhydrylamine and benzyl carbamate) were applied in the synthesis of aminophosphonates derived from pyridine, pyrrole and imidazole. The Schiff bases obtained from corresponding heterocyclic aldehydes and benzylic amines were caused to react with diphenyl phosphorate or dibenzyl phosphonate to form corresponding heterocyclic aminophosphonates in good yields. The N-(benzylamino)-phosphonates were deblocked by catalytic hydrogenolysis. The benzhydryl group from the phosphonates was removed by acidic hydrolysis, and the carbobenzyloxy group from the phosphonates can be easy removed by treatment with a solution of 30% HBr in acetic acid, as well. It was found that during acidic hydrolysis of 2-and 4-pyridylmethylaminophosphonates a rearrangement occurred, combined with a cleavage of C-P bond in the phosphonate molecules and subsequent formation of the corresponding amines.

Full text of DOI:10.1080/10426509608046390

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Phosphorus, Sulfur, and Silicon and the
Related Elements
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1-AMINOPHOSPHONIC ACIDS AND ESTERS
BEARING HETEROCYCLIC MOIETY. PART
2.1 PYRIDINE, PYRROLE AND IMIDAZOLE
DERIVATIVES
Bogdan Boduszek a
a Institute of Organic Chemistry, Biochemistry and Biotechnology,
Technical University of Wrocłlaw, Wybrzeże Wyspianskiego 27,
50-370, Wrocłlaw, Poland
Version of record first published: 04 Oct 2006
To cite this article: Bogdan Boduszek (1996): 1-AMINOPHOSPHONIC ACIDS AND ESTERS BEARING
HETEROCYCLIC MOIETY. PART 2.1 PYRIDINE, PYRROLE AND IMIDAZOLE DERIVATIVES, Phosphorus, Sulfur,
and Silicon and the Related Elements, 113:1-4, 209-218
To link to this article: http://dx.doi.org/10.1080/10426509608046390
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