Studies on the synthesis of the derivatives of 5-(dihydroxyboryl)-cytosines and-isocytosines

H Wojtowicz-Rajchel, M Suchowiak…

Index: Wojtowicz-Rajchel, Hanna; Suchowiak, Marek; Fiedorow, Piotr; Golankiewicz, Krzysztof Journal of the Chemical Society. Perkin Transactions 2, 1998 , # 4 p. 841 - 845

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Abstract

Boron derivatives of isocytosine, containing a dihydroxyboryl group in the 5-position, have been prepared for the first time. Reaction of appropriate pyrimidines with n-butyllithium and subsequent boronation at–100° C with triethylborate, followed by catalytic hydrogenation, gave hydrolytically stable N, N-dimethyl-5-(dihydroxyboryl) isocytosine 8a and N-methyl-5- (dihydroxyboryl) isocytosine 8b. Theoretical calculations suggest that the corresponding ...