Aminophosphonic derivatives of chromone. synthesis of novel chromone-3-(α-amino) methanephosphonic acids

Article abstract of DOI:10.1080/10426509808045496

Reactions of 3-formylchromones with benzyl carbamate and triphenyl phosphite in acetic acid lead to the corresponding diphenyl chromone-3-[α(-N-benzyloxycarbonyl)amino]methanephosphonates 2 in high yields. Deprotection of the Z-substituted diphenyl esters 2 by means of acetic hydrogen bromide solution and the subsequent hydrolysis by means of 20% aq. HCl, lead to the final chromone-3-(a-amino)methanephosphonic acids 4. Attempts of synthesis of the corresponding chromone-2- aminophosphonic derivatives by this way, have failed. On the other hand, chromone-2-(α-amino)methanephosphonic acid (6) was successfully obtained by an addition of tris(trimethylsilyl) phosphite to the aldimine, which was formed from the 2-formylchromone.

Full text of DOI:10.1080/10426509808045496

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Phosphorus, Sulfur, and Silicon
and the Related Elements
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AMINOPHOSPHONIC
DERIVATIVES OF CHROMONE.
SYNTHESIS OF NOVEL
CHROMONE-3-(α-AMINO)
METHANEPHOSPHONIC ACIDS
Bogdan Boduszek a , Marcin Lipiński a & Maria W.
Kowalska b
a Institute of Organic Chimestry, Biochemistry and
Biotechnology, Wroclaw University of Technology ,
50-370, Wroclaw, Poland
b Faculty University of Wroclaw , 50-383, Wroclaw,
Poland
Published online: 04 Oct 2006.
To cite this article: Bogdan Boduszek , Marcin Lipiński & Maria W. Kowalska (1998)
AMINOPHOSPHONIC DERIVATIVES OF CHROMONE. SYNTHESIS OF NOVEL CHROMONE-3-
(α-AMINO) METHANEPHOSPHONIC ACIDS, Phosphorus, Sulfur, and Silicon and the
Related Elements, 143:1, 179-189, DOI: 10.1080/10426509808045496
To link to this article: http://dx.doi.org/10.1080/10426509808045496
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