Synthesis of C??nucleoside isosteres of 9??(2??hydroxyethoxymethyl) guanine (acyclovir)

WL Mitchell, ML Hill, RF Newton…

Index: Mitchell; Hill; Newton; et al. Journal of Heterocyclic Chemistry, 1984 , vol. 21, # 3 p. 697 - 699

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Citation Number: 25

Abstract

698 WL Mitchell, ML Hill, RF Newton, P. Ravenscroft and DI С Scopes Vol. 21 presence of EEDQ, afforded the hydrazide 12. Treatment of 12 with hydrogen bromide in 2-methoxyethanol, at re- flux, caused ring closure to 13. Subsequent hydrogenolysis of the benzyl protecting group provided the acyclovir iso- stere 3 which showed the expected [6] spectral properties ('H nmr, uv and ir). Alternatively, thermal cyclization of 14 gave 15 which was ...