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In the present paper, an efficient approach for the construction of 1, N  6 -ethenoadenines from conveniently prepared N  6 -propargyl-adenines is developed. This reaction merges N -iodosuccinimide radical initiation and aerobic aminooxygenation in dioxane. This mild, 5-exo-dig , and metal-free cascade reaction could be applied to a wide substrate scope to provide 1, N  6 -ethenoadenines in moderate to good yields. The reaction mechanism was proposed and tested using radical inhibitor (butylated hydroxytoluene) and isotopic labelling ( 18 O 2 ) experiments.

rsc advances

Metal-free synthesis of 1,N6-ethenoadenines from N6-propargyl-adenines via NIS mediated radical cascade reaction