Acyl migration from N6 to N7 of a 2′,3′-O-isopropylideneadenosine derivative accompanied by cyclonucleoside formation
- 1 November 1986
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 64 (11) , 2109-2114
- https://doi.org/10.1139/v86-348
Abstract
Reaction of 2′,3′-O-isopropylideneadenosine (1) with p-NCC6H4COCl in 1:6 Et3N–CH2Cl2 afforded the cyanoimidazole nucleoside 8 (53%) and the 8,5′-O-cycloadenosine derivative 7 (29%). Treatment of N6,N6-di-p-toluyl-2′,3′-O-isopropylideneadenosine (23) with ZnBr2 in p-dioxane resulted in acyl migration from N6 to N7 to give the cycloadenosine derivative 4. The coordination site of the zinc cation on the base moiety of adenosine derivatives was determined by 15N nmr spectra.This publication has 2 references indexed in Scilit:
- Cyclonucleoside formation and ring cleavage in the reaction of 2',3'-O-isopropylideneadenosine with benzoyl chloride and its substituted derivativesThe Journal of Organic Chemistry, 1984
- 15N and 199Hg magnetic resonance spectral investigation of inosine protonation and diamagnetic metal ion complexationCanadian Journal of Chemistry, 1983