Oxidative cyclization of 2',3'-O-isopropylideneadenosines to 5'-O,8-cycloadenosines: considerations of N6-substituent effects and mechanism.
Oxidative cyclization of 2',3'-O-isopropylideneadenosines to the corresponding 5'-O,8-cyclo-2',3'-O-isopropylideneadenosines was achieved by using by lead tetraacetate, cupric chloride, and N-halogeno-succinimide as an oxidant, and by irradiation with a uv-visible light in the presence of pyrimido[5,4-g]pteridinetetrone 5-oxide. The reaction modes for the oxidative cyclization were investigated and discussed. In particular, N6-substituent effects on the oxidative cyclization provided a positive proof supporting the respective reaction mode.
Kitade
Y
Y
Laboratory of Medicinal Chemistry, Gifu Pharmaceutical University, Mitahora-higashi, Japan.
Makino
T
T
Nakanishi
R
R
Sako
M
M
Hirota
K
K
Maki
Y
Y
D000241:Adenosine / Q000031:analogs & derivatives* / Q000737:chemistry; D007700:Kinetics; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D010084:Oxidation-Reduction; D011621:Pteridines / Q000737:chemistry; D011743:Pyrimidines / Q000737:chemistry
D009942:Organometallic Compounds; D011621:Pteridines; D011743:Pyrimidines; C077694:pyrimido(5,4-g)pteridinetetrone 5-oxide, 1,3,7,9-tetrabutyl; C025132:8,5'-cycloadenosine; C029433:lead tetraacetate; D000241:Adenosine