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Palladium catalyzed coupling of 2,6-Dichloro-3-iodoimidazo[1,2-a]pyridine and 2,3-dihydrofuran as an approach to novel imidazo[1,2-a]pyridine C-nucleosides
Tetrahedron Letters ( IF 1.5 ) Pub Date : 26 August 1996 , DOI: 10.1016/0040-4039(96)01375-5
Kristjan S. Gudmundsson , John C. Drach , Leroy B. Townsend

Palladium was used for a cross coupling of 2,6-dichloro-3-iodoimidazo[1,2-a]pyridine (2) to 2,3-dihydrofuran (3). Optimization of the coupling conditions have given exclusively (+/−)-2,6-dichloro-3-(2′,5′-dihydrofuran-2′-yl)imidazo[1,2-a]pyridine (4) in high yield. Compound 4 was dihydroxylated using a catalytic amount of osmium tetroxide to give the erythrofuranosyl C-nucleoside derivatives 6 and 7. This is the first report of a C-nucleoside derivative containing a sugar moiety attached to the C3 position of an imidazo[1,2-a]pyridine heterocycle.

中文翻译:

钯催化的2,6-二氯-3-碘咪唑并[1,2- a ]吡啶和2,3-二氢呋喃的偶联反应作为新型咪唑并[1,2 - a ]吡啶C-核苷的方法

钯用于2,6-二氯-3-碘咪唑并[1,2- a ]吡啶(2)与2,3-二氢呋喃(3)的交叉偶联。偶联条件的优化专门给出了(+/-)-2,6-dichloro-3-(2',5'-dihydrofuran-2'-yl)咪唑并[1,2- a ]吡啶(4)屈服。使用催化量的四氧化将化合物4二羟基化,得到赤呋喃糖基C-核苷衍生物67。这是C-核苷衍生物的首次报道,该C-核苷衍生物含有连接至咪唑并[1,2- a ]吡啶杂环的C3位的糖部分。
更新日期:2017-01-31
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