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A New and Efficient Synthetic Method for 15N3-Labeled Cytosine Nucleosides:  Dimroth Rearrangement of Cytidine N3-Oxides

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journal contribution
posted on 12.11.2004, 00:00 by Magoichi Sako, Hiroyoshi Kawada
The treatment of 15N4-labeled cytidine N3-oxide and 15N4-labeled 2‘-deoxycytidine N3-oxide, prepared from the appropriate unprotected uridines in three reaction steps, with benzyl bromide in the presence of excess lithium methoxide allowed the smooth occurrence of their Dimroth rearrangement even under mild conditions leading to the corresponding 15N3-labeled uridine 4-O-benzyloximes which can easily undergo the reductive NO bond cleavage to give the desirable 15N3-labeled cytosine nucleosides in high total yields.