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

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Abstract
Several novel C-nucleosides were 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)-(.alpha.-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)-(.alpha.-D-arabinofuranosyl)-1,2,3,4-tetrahydro-.beta.-carboline and 4-(.alpha.-D-arabinofuranosyl)-imidazol[4,5-c]-4,5,6,7-tetrahydropyridine, respectively. The structures of the compounds were established by NMR experiments and by mass spectrometry.