Synthesis of 1-substituted 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones.
1,2-Disubstituted 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones are prepared for the first time through an activated Pictet-Spengler reaction of the corresponding imines of 2-(1,4-dimethoxynaphth-2-yl)ethylamine in the presence of an acyl chloride and AlCl(3) followed by an oxidation with silver(II) oxide in nitric acid. Depending on the reaction conditions the N-trichloroacetyl protecting group could be cleaved off, converted to an N-methoxycarbonyl group or transformed to an N-(2-oxoacetamide) moiety. The synthesized 1,2-disubstituted 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones constitute a new class of quinones, which has not been reported yet.
Laboratory of Organic Chemistry, Vrije Universiteit Brussel, Pleinlaan 2, B-1050, Brussels, Belgium.
Ekaterina
E
Shinkevich
Jurgen
J
Deblander
Sandra
S
Matthijs
Jan
J
Jacobs
Norbert
N
De Kimpe
Kourosch Abbaspour
KA
Tehrani
D003500:Cyclization; D007097:Imines / Q000138:chemical synthesis; D007546:Isoquinolines / Q000138:chemical synthesis*; D015394:Molecular Structure; D010084:Oxidation-Reduction
D007097:Imines; D007546:Isoquinolines; C039388:benzo(g)isoquinoline-5,10-dione