Chhama Awasthi

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.

Cu(OTf)2-catalysed synthesis of structurally novel bicyclic 1,3-oxazines via condensation-dehydrazinative ring transformation cascades

The Cu(OTf)2-catalysed expeditious synthesis of 1,3-oxazin-2-ones(thiones) from unprotected D-glucose and D-xylose in excellent yields is reported. Cu(OTf)2 plays a dual role of a Lewis acid and an oxidant for dehydrazination, which is the cornerstone in the present investigation. The 1,3-oxazin-2-ones(thiones) serve as synthons for diversity oriented synthesis of structurally distinct bicyclic 1,3-oxazin-2-ones(thiones), when subjected to Malaprade reaction, followed by Cu(OTf)2-catalysed cyclisation with an appropriate traditional reagent such as phenylhydrazine, amidines, hydroxylamine, or semi(thiosemi)carbazide.