| Reaction Registry Number |
RCCR07164604 |
| Reaction Step info |
3 Step |
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| Abstract |
Oxidation of the neurotoxin 6-aminodopamine (1) is known to proceed through the o-quinone 3, which undergoes intramolecular cyclisation to give 5,6-dihydroxyindole (6). In a re-examination of the reaction, we have found that at concentrations of 1 higher than 5 x 10(-3) M a quite different course prevails, leading to the formation of the novel 7-amino-8-(2-aminoethyl)-3-hydroxy-2-oxo-2,3,4, 10-tetrahydro (3,4a) iminoethanophenoxazine (7). Product 7 was formed by aerobic, chemical (persulphate, periodate) or enzymatic (tyrosinase, peroxidase/H2O2) oxidation of 1. on acetylation, 7 afforded the tetraacetate 8. Oxidation of the model compound 5-amino-4-methylcatechol (9) proceeded similarly as that of 1, to give the tetrahydrophenoxazinedione 11. |
|
| Journal article |
A NEW OXIDATION PATHWAY OF THE NEUROTOXIN 6-AMINODOPAMINE - ISOLATION AND CHARACTERIZATION OF A DIMER WITH A TETRAHYDRO(3, 4A)IMINOETHANOPHENOXAZINE RING-SYSTEM. |
| Author(s) |
NAPOLITANO A, DISCHIA M, COSTANTINI C, PROTA G |
| Institution |
NAPLES UNIV, DEPT ORGAN & BIOL CHEM, I-80134 NAPLES, ITALY. |
| Citation |
TETRAHEDRON 48(39)8515-8522(1992) |
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