โ Scribed by J. Boryski
No coin nor oath required. For personal study only.
Acyclonucleosides of Indazole and Their Rearrangements.
-Coupling reaction of indazole (I) with ether (II) under kinetically controlled conditions yields the expected 2-substituted product (III), which undergoes an irreversible, acid-catalyzed isomerization of the 2โ1 transglycosylation type furnishing regioisomer (IV). Transglycosylation product (IV) is not stable under the reaction conditions and undergoes a further, unusual rearrangement to the dimer (V). On the basis of product distributions and kinetics of product formation, a mechanism of these conversions is proposed. Regioisomers (III) and (IV), respective their unprotected forms, represent the first acyclonucleosides of indazole ever synthesized. -(BORYSKI,
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Synthesis and Antiviral Activity of Novel Aza-acyclonucleosides. -Using Mitsunobu coupling conditions the novel title compounds (VII) and (IX) are prepared.Surprisingly, they are avoid of any antiviral activity.