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

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• 作者：Sakthivel ; Kandasamy ; Cook ; P. Dan
• 关键词：Nucleosides ; 3-Deazaadenosine ; S_NAr reactions ; Fluorinated nucleosides
• 刊名：Tetrahedron Letters
• 出版年：2005
• 出版时间：May 30, 2005
• 年：2005
• 卷：46
• 期：22
• 页码：3883-3887
• 全文大小：160 K

文摘

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_NAr 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.