Naslov
Solvent- and catalyst-free transamidations of unprotected glycosyl carboxamides

Autori
Ouadah Bensalah, Fouzia ; Bil, Abed ; Wittine, Karlo ; Bellahouel, Salima ; Lesur, David ; Marković, Dean ; Laclef, Sylvain

Izvornik
Organic & biomolecular chemistry (1477-0520) 17 (2019), 43; 9425-9429

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
transamidation ; glycosyl carboxamide ; glycoconjugate, glycolipid

Sažetak
The transamidation reactions of unprotected mono- and disaccharidic carboxamides with various primary and secondary arylic, heterocyclic or aliphatic amines are described. This new method is green and atom efficient and gives good to high yields. Notably, the conditions do not require either a solvent or a catalyst and give ammonia as a single by product. The described coupling reaction is compatible with a variety of functional groups and was used in the synthesis of various glycosidic derivatives and biologically relevant glycolipids. A plausible reaction mechanism involving an intermolecular H-bond activation of the starting carboxamides is proposed.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA