The Journal of Organic Chemistry

Purine N-Oxides. XI. An Activating Effect on Some Displacement Reactions1

RM Cresswell, GB Brown

Index: Cresswell,R.M.; Brown,G.B. Journal of Organic Chemistry, 1963 , vol. 28, p. 2560 - 2563

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Citation Number: 14

Abstract

2-Mercaptoadenine 1-N-oxide was obtained from 4-aminoimidazole-5-carboxamidoxime and carbon disulfide. Methylation and oxidation afforded the 2-methylsulfinyladenine 1-N- oxide, which could be converted to the Bchloro-or the 2-hydroxyadenine N-oxides, none of which are available by direct oxidations. A comparison has been made of the reactivity of the 2-methylsulfinyl and 2-chloro groups in the N-oxides and in the corresponding free bases.