A One-Pot Synthesis of Highly Functionalized Purines,Organic Letters

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A One-Pot Synthesis of Highly Functionalized Purines
Organic Letters ( IF 4.9 ) Pub Date : 2017-11-10 00:00:00 , DOI: 10.1021/acs.orglett.7b03209
Renaud Zelli ₁ , Waël Zeinyeh _{1,

2} , Romain Haudecoeur ₁ , Julien Alliot ₁ , Benjamin Boucherle ₁ , Isabelle Callebaut ₃ , Jean-Luc Décout ₁

Affiliation

Highly substituted purines were synthesized in good to high yields through a one-pot straightforward metal-free scalable method, using the Traube synthesis adapted to Vilsmeier-type reagents. From 5-amino-4-chloropyrimidines, new 9-aryl-substituted chloropurines and intermediates for peptide nucleic acid synthesis were prepared. Variant procedures allowing a rapid synthesis of ribonucleosides and 7-benzylpurine from 5-amidino-6-aminopyrimidines are also reported to illustrate the high potential of this versatile toolbox. This route appears to be particularly interesting in the field of nucleic acids for a direct and rapid access to various new 8-alkylpurine nucleosides.

中文翻译：

一锅合成高功能嘌呤

使用适合Vilsmeier型试剂的Traube合成，通过一锅简单，无金属的可扩展方法，可以高产量合成高取代的嘌呤。由5-氨基-4-氯嘧啶，制备新的9-芳基取代的氯嘌呤和用于肽核酸合成的中间体。还报道了允许从5-ami基-6-氨基嘧啶快速合成核糖核苷和7-苄基嘌呤的各种方法，以说明这种多功能工具箱的巨大潜力。该途径在核酸领域中对于直接和快速地获得各种新的8-烷基嘌呤核苷似乎是特别令人感兴趣的。

更新日期：2017-11-10

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