Efficient, large scale-adaptable protocols are described for the straightforward conversion of D-fructose-derived 5-hydroxymethylfurfural (HMF) and of 5-glucosyloxymethylfurfural (αGMF, from isomaltulose) into hydrophilically 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.
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Lichtenthaler et al. (2001) studied this question.
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