Condensed Heterotricycles. Synthesis and reactions of b-fused 1(2H)-isoquinolinones with unusual enaminic properties

Abstract

Homophthalic acid (1) undergoes reaction with 1,2-, 1,3-, and 1,4-diamines to give condensed 1(2H)-isoquinolinones like 2, 4, 13, and 25, which exhibit marked enamine character. These are attacked by electrophiles at the N or C terminus. Some notable reactions of imidazoisoquinolone 2 are those with maleic and acrylic acids to form the tetracycles 48 and 51, respectively. With propiolic acid, 5 underwent an interesting reaction to form the benzimidazonaphthyridine 53. An equally interesting behaviour was elicited from 2 in its reaction with formaldehyde, when in addition to the expected methylene-bridged molecule 59, the novel spiro derivative 60 was formed by the dimerisation of a presumed azadiene intermediate 63.