George R. Lenz
1984
Citations
0
Influential Citations
6
Citations
Journal
Tetrahedron
Abstract
Abstract The reaction of 1-benzyl-3,4-dihydroisoquinolines with ethoxycarbonyl isocyanate yields exclusively the N-acylated product 2 . Thermal rearrangement of these enamides at 108° C. yields the pyrimidoisoquinolines 3 which may be alkylated or ethoxycarbonylated exclusively on the pyrimidone nitrogen. The pyrimidoisoquinolines possess a stilbene chromophore and are capable of undergoing the stilbene-phenanthrene conversion. Thus irradiation of 3 in the presence of iodine as a dehydrogenating agent yields the novel pyrimidoaporphine nucleus ( 7-9 ) in good yield.