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2,4-Dioxy-s-triazine aus Harnsäure und Allantoin. Isotopenversuche über den Harnsäure-Abbau, 3. Mitteilung

✍ Scribed by Hans Brandenberger; Roberta H. Brandenberger

Publisher
John Wiley and Sons
Year
1954
Tongue
German
Weight
798 KB
Volume
37
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The mechanisms of the alkaline oxidations of uric acid with H~2~O~2~ and KMnO~4~ have been investigated using isotopically labeled uric acids. The structures of the oxidation products have been examined by means of the isotope experiments and ultraviolet and infrared spectra. The following conclusions can be drawn:

Oxonic acid (allantoxanic acid) (III), allantoxaidine (IV) and their derivatives are 2,4‐dihydroxy‐1,3,5‐triazines, not imidazolidones (I and II).

The s‐triazine rings contain uric acid carbon atoms 2, 4 and 8 and nitrogen atoms 3 and 9. The third nitrogen of the ring is derived 50–50 from the former positions 1 and 7, the additional carboxyl group of oxonic acid from the uric acid carbon 5.

It has been shown for the first time in the case of uric acid itself that, during formation of allantoin, the imidazolidone rings of hydroxy‐acetylene‐diureido‐carboxylic acid (XI) split at the former uric acid position 5 and not at 4. On further degradation of allantoin, cleavage of the five‐membered ring occurs again at the former uric acid carbon 5.

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