Journal of the Chemical Society. Perkin transactions I p. 1463 - 1467 (1990)
Update date:2022-08-04
Topics:
Cornforth, John
Ming-hui, Du
The synthesis of pyrroloisoquinolinediones from phthalic anhydride and pyrrolylmagnesium halides has been improved.A new synthesis, by cyclization of the novel 1-(2-carboxybenzoyl)pyrroles, was generally preferable.From pyrrolylmagnesium bromide and dimethylmaleic anhydride, followed by cyclization, 6,7-dimethylindolizine-5,8-dione was obtained.The process failed with maleic anhydride.Pyrrolo<1,2-b>isoquinoline-5,10-dione could be dinitrated in the pyrrolo ring (with some oxidation to isoquinoline-1,3,4-trione), reduced to 10-hydroxy-3,5-dihydropyrrolo<1,2-b>isoquinolin-5-one by zinc and acetic acid, and hydrogenated over palladium on carbon to 10-hydroxy-1,2,3,5-tetrahydropyrrolo<1,2-b>isoquinolin-5-one.The dihydro derivative reverted in air to the dione.
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