Gabriel-Colman Rearrangement (Phthalimidoacetic Ester→ Rearrangement, Gabriel Isoquinoline Synthesis)

S. Gabriel, J. Colman, Ber. 33, 980, 996, 2630 (1900); 35, 2421 (1902).

Formation of isoquinoline derivatives or substituted benzothiazines by the action of alkoxides on phthalimidoacetic or saccharin esters or ketones:



C. F. H. Allen, Chem. Rev. 47, 284 (1950); H. Henecka, Houben-Weyl 8, 578 (1952); J. H. M. Hill, J. Org. Chem. 30, 620 (1965); W. C. Groutas et al., Biochem. Biophys. Res. Commun. 194, 1491 (1993); idem et al., Bioorg. Med. Chem. 3, 187 (1995); S.-K. Kwon, J. Korean Chem. Soc. 40, 678 (1996). Mechanism: M. T. Ivery, J. E. Gready, J. Chem. Res. (S) 9, 349 (1993). Cf. Dieckmann Reaction.