Photochemical coupling of 5-bromo-1,3-dimethyluracil and its 6-alkyl derivatives to 3-methylindole and N alpha-acetyl-L-tryptophan methyl ester.
Photochemical reactions between 5-bromo-1,3-dimethyluracils and 3-substituted indoles in acetone solution were studied. Irradiation (lambda greater than 290 nm) of 5-bromo-1,3-dimethyluracil (1) and N alpha-acetyl-L-tryptophan methyl ester (2) yields, in addition to 5-(2-indolyl)uracil (3), a new photoadduct 5-(7-indolyl)uracil (4). 5-Bromo-1,3-dimethyluracils with 6-alkyl substituents irradiated in the presence of 2 give the 5-(2-indolyl)uracil-type photoadducts exclusively.
Celewicz
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Adam Mickiewicz University, Faculty of Chemistry, Poznan, Poland.
D002855:Chromatography, Thin Layer; D007211:Indoles / Q000032:analysis*; D009682:Magnetic Resonance Spectroscopy; D010777:Photochemistry; D012862:Skatole / Q000032:analysis* / Q000528:radiation effects; D014364:Tryptophan / Q000032:analysis / Q000528:radiation effects / Q000031:analogs & derivatives; D014466:Ultraviolet Rays; D014498:Uracil / Q000031:analogs & derivatives* / Q000032:analysis / Q000528:radiation effects
D007211:Indoles; D014498:Uracil; C061430:5-bromo-1,3-dimethyluracil; D014364:Tryptophan; D012862:Skatole; C029614:N-acetyltryptophan methyl ester