6533b85afe1ef96bd12b94e2

RESEARCH PRODUCT

New electrophilic reactions of 2,2′-bisindolyls with acid chlorides and carbodienophiles

Ulf PindurY.-s. Kim

subject

chemistry.chemical_classificationAcylationIndole testchemistry.chemical_compoundchemistryOrganic ChemistryElectrophileAnthranilic acidDehydrogenationAldehydeMedicinal chemistryAryne

description

Some new acylation and cyclization reactions of 2,2′-bisindolyls 1, 2 are described. The product patterns constitute acyl derivatives 3, 4, 5 and an aldehyde 7, indolo[2,3-a]carbazoles 6, 14, 17, 19, 20 and cyclopentadiindoles 22 and 24. In the reaction with aryne or diazotated anthranilic acid, a 3-benzoylindole derivative 9 and phenylindolyl azo dye 10 are formed. N-methylmaleimide reacts with 2,2′-bisindolyl 2 via Michael type addition, dehydrogenation and cyclization to several functionalized or anellated indole derivatives 11, 12, 13 and 14, respectively.

https://doi.org/10.1002/jhet.5570330317