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Plieninger-Moody carbazole synthesis

Scheme 4 Variations on the Plieninger-Moody Carbazole Synthesis... Scheme 4 Variations on the Plieninger-Moody Carbazole Synthesis...
The first example of an indole-2,3-quinodimethane (IQM) undergoing a Diels-Alder cycloaddition to furnish a carbazole was reported by Plieninger and coworkers in 1964 [9], Thus, indole-3-acetic acid was readily converted to pyrano[3,4-fe]indol-3-ones upon treatment with carboxylic acid anhydrides (Scheme 1, equation 1). These stable synthetic equivalents of IQMs undergo Diels-Alder reactions with electron-deficient dienophiles (A-phenytma-leimide,maleicanhydride,dimethylacetylenedicarboxylate) (equation 2). Plieninger s discovery notwithstanding, it was Moody and coworkers who parlayed this chemistry into a powerful carbazole synthesis (equations 3,4) [10-18],... [Pg.437]

See other pages where Plieninger-Moody carbazole synthesis is mentioned: [Pg.438]    [Pg.438]    [Pg.437]   
See also in sourсe #XX -- [ Pg.437 , Pg.438 , Pg.440 ]



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