Regioselective nitration of purine nucleosides: synthesis of 2-nitroadenosine and 2-nitroinosine

被引：23

作者：

Deghati, PYF ^{[1
]}

Wanner, MJ ^{[1
]}

Koomen, GJ ^{[1
]}

机构：

[1] Univ Amsterdam, Inst Mol Chem, Organ Chem Lab, NL-1018 WS Amsterdam, Netherlands

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 08期

关键词：

nitration; adenosine; inosine;

D O I：

10.1016/S0040-4039(99)02271-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nitration reactions of 6-substituted purine nucleosides with tetrabutylammonium nitrate/trifluoroacetic anhydride (TBAN/TFAA) have been studied. This nitrating mixture selectively nitrates C-6 substituted purines at the 2-position, but the method is limited to substrates without NH or OH substituents. Acetylated 6-chloropurine riboside was cleanly nitrated (DCM, 0 degrees C, 71%) and converted to nitro substituted adenosine and inosine in a few simple steps. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1291 / 1295

页数：5

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