Tetrahedron

Addition of electrophilic radicals to caffeine: synthetic aspects and influence of the peroxidic initiators

J Zylber, L Ouazzani-Chahdi, D Lefort, A Chiaroni…

Index: Zylber, J.; Ouazzani-Chahdi, L.; Lefort, D.; Chiaroni, A.; Riche, C. Tetrahedron, 1989 , vol. 45, # 3 p. 721 - 732

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Citation Number: 8

Abstract

Primary and secondary electrophilic radicals such as:. CHRCO2CH3 (R= H, CH3, CO2CH3) and tertiary. CCl3, radical were added directly at C-8 of, the model purine compound, caffeine to give the corresponding 8-substituted derivatives in fairly good yields. Unexpected reaction of caffeine with oxy radicals from the initiators (PhCo2., t-BuOO.) gave rise to C-5 substituted 1, 3, 7-trimethyl-5, 7-dihydrouric acid derivatives (C-5-R= CCl3 CH3, C (CH3) ...