A Simple Conversion of Creatinine to Creatol via Creatinine Chloroamine
Kazuharu Ienaga A D , Yoshiaki Toya B , Kiyohiko Nakajima B and Mariko Tachikawa CA Nippon Zoki Pharmaceutical Co., 1-2 Hiranomachi, Nichome, Chuo-ku, Osaka 541-0046, Japan.
B Faculty of Education, Aichi University of Education, 1 Hirosawa, Igaya-cho, Kariya, Aichi 448-8542 Japan.
C School of Pharmacy, Nihon University, 7-7-1 Narashinodai, Funabashi, Chiba, 274-8555, Japan.
D Corresponding author. Email: k-ienaga@nippon-zoki.co.jp
Australian Journal of Chemistry 68(2) 248-253 https://doi.org/10.1071/CH14476
Submitted: 29 July 2014 Accepted: 17 September 2014 Published: 5 November 2014
Abstract
Creatinine (2-amino-1,5-dihydro-l-methylimidazol-4-one) (1a) was converted in a simple way to creatol (2-amino-1,5-dihydro-5-hydroxy-l-methylimidazol-4-one) (1b) via creatinine chloramine (2-N-chloroamino-1,5-dihydro-l-methylimidazol-4-one) (3a), without using protecting groups. The creatinine chloroamine exists in the 2-N-chloroamino form (3a) in aqueous solution, but in the solid state, X-ray crystal analysis shows that it has the 2-N-chloroimino structure (2-N-chloroimino-1,5-dihydro-1-methylimidazol-4-one) (4a). Related imidazolones have also been prepared and are discussed.
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