Sugar-derived building blocks. Part 26. Hydrophilic pyrroles, pyridazines and diazepinones from D-fructose and isomaltulose

Authors
Lichtenthaler, FW Brust, A Cuny, E
Citation
Fw. Lichtenthaler et al., Sugar-derived building blocks. Part 26. Hydrophilic pyrroles, pyridazines and diazepinones from D-fructose and isomaltulose, GREEN CHEM, 3(5), 2001, pp. 201-209
Citations number
36
Categorie Soggetti
Chemistry
Journal title
GREEN CHEMISTRY
ISSN journal
14639262 → ACNP
Volume
3
Issue
5
Year of publication
2001
Pages
201 - 209
Database
ISI
SICI code
1463-9262(200110)3:5<201:SBBP2H>2.0.ZU;2-D
Abstract
Efficient, large scale-adaptable protocols are described for the straightfo rward conversion of D-fructose-derived 5-hydroxymethylfurfural (HMF) and of 5-glucosyloxymethylfurfural (alpha GMF, from isomaltulose) into hydrophili cally substituted N-heterocycles of the pyrrole, pyridazine, thiophene and benzodiazepine type. Key intermediates are 1,6-dihydroxy-2,5-hexenediones, readily generated by oxidative furan ring-opening.