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Dodd, Azita (1990) Studies of 3-hydroxypyrid-4-ones and related ligands. Doctoral thesis, Polytechnic of North London.
It has been established that the previous synthetic route to 3-benzyloxy-l, 2-dimethylpyrid-4-one and l,2-dimethyl-3-hydroxypyrid-4-one, under the reported conditions, does not lead to their free bases but to their protonated forms. The structures of those pyridones in both free base and protonated forms have been clarified by spectroscopic techniques and a hydroxypridinium structure is proposed for the salts. The direct synthesis of l,2-dimethlyl-3- hydroxyprid-4-one, has also been achieved by Modifying a reported route.
Two new, and general synthetic routes have been investigated in a preliminary way. One route involving the reaction of l-bromobutano-2,3-diono with N?-methylbenzamide, has Ied to the recovery of the starting axide and decomposition of the bromo compound. The second route involves the use of pyridine as the starting material. In this study, 1-ethoxycarbonylpiperidene-3,4- diol was synthesised using a previously reported procedure. The oxidation of this diol with Jones' reagent gave a mixture of products, one of which was identified as the desired product, 1-ethoxycarbonylpiperidene-3,4-dione using G.C.-mass spectrometry techniques. ...
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