Pictet–Spengler reaction of biogenic amines with carbohydrates. Synthesis of novel C-nucleosides

Abstract

Several novel C-nucleosides have been prepared by Pictet–Spengler condensations between biogenic amines and carbohydrates. Dopamine hydrochloride reacted with D-glucose to give 6,7-dihydroxy-1(R)- and -1(S)-(D-gluco-pentitol-1′-yl)-1,2,3,4-tetrahydroisoquinoline hydrochlorides, and with 2,5-anhydro-D-mannose to give 1(R)- and 1(S)-(α-D-arabinofuranosyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochlorides. Tryptamine hydrochloride and histamine did not react with D-glucose, but with 2,5-anhydro-D-mannose gave 1(R)- and 1(S)-(α-D-arabinofuranosyl)-1,2,3,4-tetrahydro-β-carboline and 4-(α-D-arabinofuranosyl)-imidazo[4,5-c]-4,5,6,7-tetrahydropyridine, respectively. The structures of the compounds have been established by nmr experiments and by mass spectrometry.