从碳水化合物出发高效一锅合成含亚氨基糖的咪唑并[1,2-a]吡啶。
Efficient one-pot synthetic protocols for iminosugar-bearing imidazo[1,2-a]pyridines from carbohydrates.
机构信息
Green Synthesis Lab, Department of Chemistry, University of Allahabad, Allahabad 211 002, India.
出版信息
Carbohydr Res. 2010 Jan 26;345(2):318-23. doi: 10.1016/j.carres.2009.11.016. Epub 2009 Nov 13.
This letter describes two unprecedented one-pot high yielding synthetic approaches to imidazo[1,2-a]pyridine scaffolds from carbohydrates. The first approach involves microwave-assisted acid-catalyzed domino reactions of unprotected D-glucose/D-xylose with ammonium acetate and benzoin to afford polyhydroxy iminosugar-bearing tetrahydroimidazo[1,2-a]pyridines. In the second approach, polyhydroxy iminosugar-bearing tetrahydrobenzimidazo[1,2-a]pyridines were synthesized by using unprotected D-glucose/D-xylose and 1,2-diamines in the presence of 10 mol% of oxalic acid under solvent-free microwave irradiation conditions.
这封信描述了两种前所未有的一锅法高产合成咪唑并[1,2-a]吡啶骨架的方法，均来自碳水化合物。第一种方法涉及在微波辅助下，未保护的 D-葡萄糖/D-木糖与醋酸铵和苯偶姻进行酸催化的多米诺反应，生成带有多羟基亚氨基糖的四氢咪唑并[1,2-a]吡啶。在第二种方法中，在无溶剂微波照射条件下，使用未保护的 D-葡萄糖/D-木糖和 1,2-二胺，在 10 mol%草酸的存在下，合成了带有多羟基亚氨基糖的四氢苯并咪唑并[1,2-a]吡啶。
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