Contribution No. 822 from Hindustan Ciba-Geigy Ltd., Research Centre.
Condensed Heterotricycles. Synthesis and Reactions of b-Fused 1(2H)-Isoquinolinones with unusual enaminic properties†
Article first published online: 25 OCT 2004
Copyright © 1988 Verlag GmbH & Co. KGaA, Weinheim
Helvetica Chimica Acta
Volume 71, Issue 1, pages 77–92, 3 February 1988
How to Cite
Nagarajan, K., Rao, V. R., Shah, R. K., Shenoy, S. J., Fritz, H., Richter, W. J. and Muller, D. (1988), Condensed Heterotricycles. Synthesis and Reactions of b-Fused 1(2H)-Isoquinolinones with unusual enaminic properties. HCA, 71: 77–92. doi: 10.1002/hlca.19880710110
- Issue published online: 25 OCT 2004
- Article first published online: 25 OCT 2004
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.