Original scientific paper

Synthesis of Some Pyridoxine and Pyridoxal Halophosphonates

Sadik Elshani ; Department of Chemistry, The College of Arts and Sciences, University of Idaho, Moscow, Idaho, USA
Ljubica Butula ; Faculty of Pharmacy and Biochemistry, University of Zagreb, 10000 Zagreb, Croatia
Julija Matijević-Sosa ; Faculty of Pharmacy and Biochemistry, University of Zagreb, 10000 Zagreb, Croatia

Abstract

A new series of pyridoxine and pyridoxal chloro and fluorophosphonates have been synthesized. Partially protected pyridoxine 1, 2 or pyridoxal 4 reacted with methyl phosphonic dichloride in the presence of triethylamine at -10 °C. Thus, the following chlorophosphonate derivatives were obtained: 3,4'-0-isopropylidenepyridoxine-5'-0- methylchlorophosphonate (5), 4',5'-0-isobutylidenepyridoxine-3-0- methylchlorophosphonate (6), and monoethylacetalpyridoxal-3-0- methylchlorophosphonate (7). Similarly, from adequate starting compounds 1,3 and unprotected pyridoxal (PL) in the reaction with methyl phosphonic difluoride and triethylamine, near O"C, the corresponding 3-0 or 5'-0-methylfluorophosphonateswere obtained; 3,4'-0 isopropylidenepyridoxine-5'-0-methylfluorophosphonate(8), 4-metoxymethylpyridoxine- 5'-0-methylfluorophosphonate (9) and pyridoxal- 5'-0-methylfluorophosphonate (10).

Keywords

Hrčak ID:

177142

URI

https://hrcak.srce.hr/177142

Publication date:

1.11.1996.

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