Showing papers on "Glucal published in 2019"

Synthesis of amidoglucals and glucal esters via carbonylative coupling reactions of 2-iodoglucal using Mo(CO)6 as a CO source

Abstract: The synthesis of amidoglucals and glucal esters in good to high yields using 2-iodo-3,4,6-tri-O-acetyl-D-glucal as a substrate, Mo(CO)6 as a carbon monoxide source and PdCl2 as a catalyst is reported. This procedure shows advantages when compared to other published methodologies, as it is carried out in one pot relying on short reaction times at mild temperatures, under ligand-free conditions and with only one equivalent of Mo(CO)6.

One-Pot Cascade Transformation of Glucal into Structurally Diverse Drug-Like Scaffolds.

Abstract: A diversity-oriented synthesis strategy to produce three types of structurally drug-like N-heterocyclic-fused rings has been developed from abundant biomass-derived d-glucal, aniline and water in a stereoselective manner. The overall transformation which entails a cascade of Ferrier reaction and 4π conrotatory imino-Nazarov cyclization was performed in one-pot allowing convenient preparation of scaffolds of high molecular complexity from relatively simple starting materials. While indoline-fused products were readily accessible using ortho-unsubstituted secondary anilines as substrates, reactions with ortho-hydroxyl-anilines furnished fused 1,4-benzoxazines instead. In both cases, InBr3 acted as the Lewis acid catalyst. By altering InBr3 to Ln(OTf)3 , the indoline-fused products could be further converted into tetrahydroquinoline-fused cyclopentenones via ensuing retro-ene rearrangement.