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Metal-free synthesis of 1,N ⁶-ethenoadenines from N ⁶-propargyl-adenines via NIS mediated radical cascade reaction.

ABSTRACT: 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 (¹⁸O₂) experiments.

SUBMITTER: Yang R

PROVIDER: S-EPMC9075968 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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Metal-free synthesis of 1,N 6-ethenoadenines from N 6-propargyl-adenines via NIS mediated radical cascade reaction.

Yang Ruchun R Deng Si S Dong Xiang-You XY Song Xianrong X Cai Hu H Bai Jiang J Xiao Qiang Q

RSC advances 20191126 66

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 ...[more]

PMID: 35540232

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