A novel [2 + 2] photodimerization of N-[(E)-3,4-methylenedioxycinnamoyl]dopamine in the solid state.
[reaction: see text] To give photoreactivity to catecholamines, N-cinnamoyl-substituted dopamines (E)-5a-5c and O,O'-dimethyldopamines (E)-3a-3c were prepared under solvent-free conditions. A particularly interesting observed photoreactivity was that of N-[(E)-3,4-methylenedioxycinnamoyl]dopamine ((E)-5c), which underwent a novel type of [2 + 2] photodimerization in the solid state, giving exclusively a tricyclic product 8. This reaction is the first example of solid-state photoaddition of an alkene to the benzene ring.
Ito
Y
Y
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 606-8501, Japan. yito@sbchem.kyoto-u.ac.jp
Horie
S
S
Shindo
Y
Y
D002934:Cinnamates / Q000737:chemistry*; D018360:Crystallography, X-Ray; D019281:Dimerization; D004298:Dopamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010777:Photochemistry
D002934:Cinnamates; C433948:N-(3,4-methylenedioxycinnamoyl)dopamine; D004298:Dopamine