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Review | Regular issue | Vol 23, No. 3, 1985, pp.731-740
Published online, 1st January, 1970
DOI: 10.3987/R-1985-03-0731
Ring Annelations via Reissert Compounds

Frank D. Popp* and Barrie C. Uff

*Department of Chemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53201, U.S.A.

Abstract

Conversion of isoquinoline and related heterocycles to the corresponding Reissert compound provides a starting point for the annelation of an additional ring. This has proved an attractive route to a wide range of ring systems. The review discusses the versatility of such procedures which include cycloaddition of cyclic Reissert salts with alkynes, addition of Reissert compound conjugate bases to suitable Michael acceptors, intramolecular cyclisations of Reissert compounds derived from chloroalkyl-substituted acid chlorides, the reaction of conjugate bases of chloroformate derived Reissert compound analogs with suitable electrophiles including heterocumulenes, and other methods. Annelations are exemplified with a variety of heterocycles in addition to isoquinoline and quinoline, including phthalazine, phenanthridine and 3,4-dihydro-β-carboline.