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The novel imido esters of 2-deoxy-α- and -β-D-ribose 8 and 9 have been synthesized and successfully transformed to the protected 1,2,4-triazine-C -nucleosides 11 and 12 using an inverse type Diels-Alder reaction with the 1,2,4,5-tetrazine 10. The electron deficient diazadiene system of both C -nucleosides 11 and 12 proved to be highly reactive in a consecutive [4 + 2] cycloaddition with inverse electron demand towards several electron rich dienophiles yielding after successful deprotection the novel pyridine-, pyrindine- and isoquinoline-C-nucleosides 15, 18 and 21 of 2 -deoxy-α-D-ribose and 23, 25 and 27 of 2-deoxy-β-D-ribose.

zeitschrift für naturforschung b

Synthese neuer Pyridin-, Pyrindin- bzw. Isochinolin-substituierter α- und β-C-Nukleoside der 2-Desoxy-D-ribose / Synthesis of Novel Pyridine-, Pyrindine- and Isoquinoline-Substituted α- and β-C-Nucleosides of 2-Deoxy-D-ribose