Oxidation of uric acid. 4. Synthesis, structure, and diabetogenic action of 5-imino-2, 4, 6 (1H, 3H, 5H)-pyrimidinetrione salts and their alloxan-like covalent adducts
Three synthetic routes to salts of 5-amino-5-hydroxy-2, 4, 6 (lH, 3H, SH)-pyrimidinetrione (10) are described. The key reactions involved acid-catalyzed cleavage of 5-amino-5-ureido- 2, 4, 6 (lH, 3H, 5H)-pyrimidinetrione (7), conversion of uramil (8) to dehydrouramil (9) and subsequent hydration, and the condensation of alloxan (5) with ammonium salts. The carbinol ammonium salt structure 10a was unambiguously established by X-ray ...
