Efficient one-pot synthetic protocols for iminosugar-bearing imidazo[1,2-a]pyridines from carbohydrates.
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.
Yadav
Lal Dhar S
LD
Green Synthesis Lab, Department of Chemistry, University of Allahabad, Allahabad 211 002, India. ldsyadav@hotmail.com
Awasthi
Chhama
C
D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D005947:Glucose / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry*; D008872:Microwaves; D014994:Xylose / Q000737:chemistry
D002241:Carbohydrates; D007093:Imidazoles; C029899:imidazole; D014994:Xylose; D005947:Glucose