Regioselective amination of carbaporpholactone and N-confused porphyrin.
An efficient route to the direct amination at the inner carbon of carbaporpholactone is reported. A regioselectivity of substitution is enforced by activation of the embedded furanone fragment due to coordination of the highly oxidized silver(III) cation. A stepwise oxidation of the dimethylamine derivative leads to the internally bridged carbaporpholactones which contain respectively [5.7.5] tricyclic or [5.7.5.7.5] pentacyclic rings. The analogous reactivity of N-confused porphyrin has been also explored.
Grzegorzek
Norbert
N
Department of Chemistry, University of Wrocław, 14 F. Joliot-Curie St., Wrocław 50 383, Poland.
Pawlicki
Miłosz
M
Latos-Grazyński
Lechosław
L
D000586:Amination; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D011166:Porphyrins / Q000737:chemistry*; D013237:Stereoisomerism
D011166:Porphyrins; C546485:carbaporpholactone