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Heterocyclic Imines and Amines. Part 19. Isoquinoline and Other Products from α,o-Dicyanostilbene and Basic Reagents
Barnard, Ian F.,Elvidge, John A.
, p. 1813 - 1818 (2007/10/02)
α,o-Dicyanostilbene (1) was cleaved by hydrazine or hydroxylamine under mildly acid conditions to o-cyanobenzyl cyanide (2) and benzaldehyde, isolated as derivatives.Sodamide with compound (1) gave 1-amino-4-cyano-3-phenylisoquinoline: alkoxides similarly gave the 1-alkoxy compounds, the presumed intermediate 3,4-dihydroisoquinoline from the methoxide reaction being isolated and separately dehydrogenated.Acid hydrolysis of the 1-ethoxy compound gave the known 4-cyano-3-phenylisoquinolin-1(2H)-one.With the anion of o-cyanobenzyl cyanide, compound (1) gave a 1-amino-4-cyano-3-(2-substituted phenyl)isoquinoline, which was oxidised to 1-amino-4-cyano-3-(2-carboxyphenyl)isoquinoline.The latter lost water at 210 deg C to give yellow 12-cyano-5-iminoisoindoloisoquinolin-7(5H)-one, closely related to known compounds.
