Direct SNAr amination of fluorinated imidazo[4,5-c]-pyridine nucleosides:: efficient syntheses of 3-fluoro-3-deazaadenosine analogs

被引：10

作者：

Sakthivel, K ^{[1
]}

Cook, PD ^{[1
]}

机构：

[1] Biota Inc, Carlsbad, CA 92008 USA

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 22期

关键词：

nucleosides; 3-deazaadenosine; SNAr reactions; fluorinated nucleosides;

D O I：

10.1016/j.tetlet.2005.03.190

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This paper describes the ready preparation of 3,6-difluoro-3-deazapurine (4,7-difluoroimidazo[4,5-c]pyridine). This novel base was glycosylated under mild conditions using three different ribose sugar analogs. 3,6-Difluoro-3-deazapurine ribonucleoside analogs underwent direct S(N)A(r) amination reactions with liquid ammonia to give 3 -fluoro- 3 -deazaadenosine analogs in excellent yield; in contrast, 6-chloro-3-fluoro-3-deazapurine nucleosides were inert under similar reaction conditions. © 2005 Elsevier Ltd. All rights reserved.

引用

页码：3883 / 3887

页数：5

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