Synthesis and antiviral properties of 5-(2-substituted vinyl)-6-aza-2'-deoxyuridines

WL Mitchell, P Ravenscroft, ML Hill…

Index: Mitchell, William L.; Ravenscroft, Paul; Hill, Malcolm L.; Knutsen, Lars J.S.; Judkins, Brian D.; et al. Journal of Medicinal Chemistry, 1986 , vol. 29, # 5 p. 809 - 816

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Citation Number: 22

Abstract

Our first synthesis of 6-aza-BVDU (2) required (E)-5-(2-bromovinyl)-6-azauracil (12). 5- (Hydroxymethyl)-6-azauracil (8), conveniently obtained by hydrolysis of the corresponding chloromethyl derivative 9, 9 was oxidized to the carboxaldehyde 10 in high yield with use of benzeneseleninic anhydride.'O The remaining steps in the preparation of 12 paralleled those employed by Jones et al. for the synthesis of (E)-5-(2-bromovinyl) uracil. 11 Thus, ...