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作为离去基团的1,2,3-三唑:2,6-双三唑基嘌呤与O-和C-亲核试剂的芳基亲核取代反应

1,2,3-Triazoles as leaving groups: SAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles.

作者信息

Cīrule Dace, Novosjolova Irina, Bizdēna Ērika, Turks Māris

机构信息

Faculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, Latvia.

出版信息

Beilstein J Org Chem. 2021 Feb 11;17:410-419. doi: 10.3762/bjoc.17.37. eCollection 2021.

Abstract

A new approach was designed for the synthesis of C6-substituted 2-triazolylpurine derivatives. A series of substituted products was obtained in SAr reactions between 2,6-bistriazolylpurine derivatives and O- and C-nucleophiles under mild conditions. The products were isolated in yields up to 87%. The developed C-O and C-C bond forming reactions clearly show the ability of the 1,2,3-triazolyl ring at the C6 position of purine to act as leaving group.

摘要

设计了一种合成C6-取代的2-三唑基嘌呤衍生物的新方法。在温和条件下,2,6-双三唑基嘌呤衍生物与O-和C-亲核试剂之间通过亲核芳香取代反应(SAr反应)得到了一系列取代产物。产物的分离产率高达87%。所开发的C-O和C-C键形成反应清楚地表明嘌呤C6位的1,2,3-三唑基环能够作为离去基团。

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