Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Triflimide-Promoted Nucleophilic C-Arylation of Halopurines to Access N7-Substituted Purine Biaryls
Toshitaka ShojiKosuke FukushimaTakayuki MenjoYoichi YamadaTomonori HanasakiKotaro KikushimaNaoko TakenagaToshifumi Dohi
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2021 Volume 69 Issue 9 Pages 886-891

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Abstract

Functionalized nucleobases are utilized in a wide range of fields; therefore, the development of new synthesis methods is essential for their continued application. With respect to the C6-arylation of halopurines, which possess a substituent at the N7-position, only a small number of successful cases have been reported, which is predominately a result of large steric hinderance effects. Herein, we report efficient and metal-free C6-arylations and SNAr reactions of N7-substituted chloropurines in aromatic and heteroatom nucleophiles promoted by triflimide (Tf2NH) in fluoroalcohol.

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